the ir spectra were obtained as kbr pellets in the range of 4004,000  cm on a shimadzu model 460 spectrophotometer . h nmr spectra were recorded at 400  mhz , and c nmr spectra were recorded at 100  mhz in dmso - d6 . the chemical shifts are reported in ppm (  ) , and referenced to the residual proton signal for dmso - d6 ( 2.49  ppm ) . mass spectrometric data ( ms ) were obtained by electron ionization ( ei , 70  ev ) or electrospray ionization ( esi ) . a mixture of 199  mg 2,3-dichloroquinoxaline ( 1.0  mmol ) , 0.1  cm hydrazine hydrate ( 99  % , 2.0  mmol ) , a suitable aldehyde ( 1.0  mmol ) , and 0.05  cm bromine ( 1.0  mmol ) were stirred in 5  cm h2o at room temperature under an argon atmosphere for 30  min . phenylacetylene ( 0.11  cm , 1  mmol ) , 53  mg pd / c ( 10  % , 0.05  mmol ) , and 276  mg k2co3 ( 2.0  mmol ) were added , and the resulting solution was heated at 70  c for 12  h , and then cooled to room temperature . the residue was purified by chromatography , eluting with chcl3/ch3oh ( 98:2 ) to afford the pure product ( table  2 ) . white solid ; yield 283  mg ( 82  % ) ; m.p . : 280282  c ; rf  =  0.53 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,200 , 1,650  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.327.42 ( m , 4h ) , 7.457.55 ( m , 4h ) , 7.67 ( d , j  =  4.8  hz , 1h ) , 7.81 ( d , j  =  4.1  hz , 1h ) , 7.867.92 ( m , 3h ) , 8.058.08 ( m , 1h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.26 , 96.37 , 123.80 , 127.55 , 127.85 , 128.11 , 128.21 , 128.70 , 128.95 , 129.22 , 129.55 , 129.76 , 130.45 , 132.10 , 132.45 , 138.92 , 142.17 , 145.11 , 149.12  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  346 ( [ m ] , 100 ) , 269 ( 52 ) , 245 ( 22 ) , 167 ( 16 ) ; hrms ( esi ) : m / z  =  346.1201 . white solid ; yield 367  mg ( 94  % ) ; m.p . : 284286  c ; rf  =  0.55 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,200 , 1,600 , 1,540 , 1,340  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.567.63 ( m , 3h ) , 7.737.75 ( m , 1h ) , 7.807.87 ( m , 3h ) , 7.95 ( dd , j  =  6.4 , 2.0  hz , 2h ) , 8.058.10 ( m , 2h ) , 8.168.19 ( m , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.39 , 96.45 , 121.36 , 122.72 , 127.45 , 128.25 , 128.35 , 128.47 , 128.66 , 129.42 , 129.58 , 129.68 , 131.36 , 132.45 , 132.60 , 135.54 , 142.36 , 145.78 , 149.25  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  391 ( [ m ] , 100 ) , 345 ( 32 ) , 314 ( 51 ) , 290 ( 21 ) , 169 ( 24 ) ; hrms ( esi ) : m / z  =  391.1037 . white solid ; yield 289  mg ( 74  % ) ; m.p . : 274276  c ; rf  =  0.52 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,230 , 1,610 , 1,530 , 1,340  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.28 ( s , 1h ) , 7.357.40 ( m , 2h ) , 7.467.52 ( m , 3h ) , 7.547.60 ( m , 3h ) , 7.647.71 ( m , 3h ) , 8.038.06 ( m , 1h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.26 , 96.35 , 121.10 , 122.45 , 127.52 , 128.45 , 129.26 , 129.45 , 129.64 , 129.88 , 130.20 , 131.36 , 132.25 , 132.45 , 142.36 , 145.56 , 148.92 , 149.55  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  391 ( [ m ] , 100 ) , 345 ( 35 ) , 314 ( 43 ) , 290 ( 26 ) , 167 ( 21 ) ; hrms ( esi ) : m / z  =  391.1042 . white solid ; yield 367  mg ( 94  % ) ; m.p . : 293295  c ; rf  =  0.54 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,210 , 1,620 , 1,540 , 1,320  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.40 ( d , j  =  8.4  hz , 1h ) , 7.557.61 ( m , 4h ) , 7.687.71 ( m , 1h ) , 7.807.86 ( m , 2h ) , 8.118.18 ( m , 3h ) , 8.55 ( d , j  =  8.2  hz , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  84.95 , 96.35 , 116.61 , 120.60 , 124.75 , 126.02 , 128.50 , 129.68 , 130.72 , 131.29 , 132.14 , 132.85 , 134.87 , 135.97 , 136.09 , 145.33 , 148.53 , 149.46  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  391 ( [ m ] , 100 ) , 345 ( 40 ) , 314 ( 47 ) , 290 ( 18 ) , 168 ( 29 ) ; hrms ( esi ) : m / z  =  391.1047 . white solid ; yield 276  mg ( 76  % ) ; m.p . : 305307  c ; rf  =  0.50 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,250 , 1,570  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.20 ( s , 1h ) , 7.357.43 ( m , 4h ) , 7.577.64 ( m , 4h ) , 7.827.86 ( m , 2h ) , 8.21 ( d , j  =  8.0  hz , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.80 , 96.42 , 116.62 , 122.26 , 122.92 , 124.85 , 127.70 , 128.37 , 128.81 , 129.21 , 130.35 , 130.56 , 133.51 , 133.65 , 141.52 , 146.23 , 146.56 , 149.55 , 160.42  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  364 ( [ m ] , 100 ) , 345 ( 27 ) , 287 ( 62 ) , 263 ( 42 ) , 167 ( 25 ) ; hrms ( esi ) : m / z  =  364.1152 . white solid ; yield 309  mg ( 85  % ) ; m.p . : 313315  c ; rf  =  0.51 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,230 , 1,590  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.20 ( s , 1h ) , 7.357.41 ( m , 2h ) , 7.557.62 ( m , 2h ) , 7.787.82 ( m , 2h ) , 7.907.98 ( m , 4h ) , 8.158.19 ( m , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.82 , 96.44 , 116.36 , 116.45 , 122.32 , 126.22 , 127.32 , 128.24 , 128.55 , 128.74 , 128.92 , 129.20 , 130.35 , 130.47 , 132.10 , 132.21 , 142.30 , 145.25 , 149.25 , 162.92  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  364 ( [ m ] , 100 ) , 345 ( 32 ) , 287 ( 67 ) , 263 ( 35 ) , 167 ( 29 ) ; hrms ( esi ) : m / z  =  364.1144 . white solid ; yield 315  mg ( 83  % ) ; m.p . : 276278  c ; rf  =  0.56 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,250 , 1,600  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.35 ( s , 1h ) , 7.437.52 ( m , 4h ) , 7.607.70 ( m , 4h ) , 8.068.12 ( m , 2h ) , 8.40 ( d , j  =  8.0  hz , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.65 , 96.53 , 123.42 , 127.53 , 127.65 , 128.21 , 128.32 , 128.42 , 128.65 , 129.25 , 129.64 , 130.36 , 130.54 , 132.25 , 132.36 , 132.46 , 138.65 , 142.35 , 145.65 , 149.58  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  382 ( [ m][cl ] , 31 ) , 380 ( [ m][cl ] , 100 ) , 345 ( 35 ) , 303 ( 57 ) , 279 ( 21 ) , 167 ( 25 ) ; hrms ( esi ) : m / z  =  380.0850 . white solid ; yield 326  mg ( 86  % ) ; m.p . : 289291  c ; rf  =  0.55 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,240 , 1,600  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.417.45 ( m , 1h ) , 7.557.63 ( m , 4h ) , 7.657.69 ( m , 1h ) , 7.717.77 ( m , 3h ) , 7.85 ( d , j  =  8.0  hz , 2h ) , 8.118.18 ( m , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.01 , 96.20 , 116.25 , 120.63 , 126.18 , 127.49 , 128.34 , 129.68 , 129.85 , 130.60 , 131.27 , 132.45 , 132.83 , 136.03 , 136.46 , 136.80 , 145.11 , 149.14  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  382 ( [ m][cl ] , 32 ) , 380 ( [ m][cl ] , 100 ) , 345 ( 30 ) , 303 ( 62 ) , 279 ( 26 ) , 168 ( 20 ) ; hrms ( esi ) : m / z  =  380.0850 . white solid ; yield 310  mg ( 75  % ) ; m.p . : 267269  c ; rf  =  0.57 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,210 , 1,620  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.20 ( s , 1h ) , 7.407.48 ( m , 4h ) , 7.557.62 ( m , 3h ) , 7.757.78 ( m , 2h ) , 8.128.15 ( m , 1h ) , 8.178.20 ( m , 1h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.35 , 96.23 , 127.80 , 127.95 , 128.44 , 128.84 , 128.92 , 129.10 , 129.25 , 129.54 , 130.92 , 131.44 , 132.35 , 132.74 , 133.55 , 138.22 , 142.62 , 145.84 , 149.12  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  418 ( [ m][cl2 ] , 12 ) , 416 ( [ m][cl][cl ] , 53 ) , 414 ( [ m][cl2 ] , 100 ) , 381 ( 23 ) , 339 ( 65 ) , 313 ( 30 ) , 269 ( 32 ) , 168 ( 15 ) ; hrms ( esi ) : m / z  =  414.0475 . white solid ; yield 288  mg ( 80  % ) ; m.p . : 218220  c ; rf  =  0.52 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,220 , 1,600  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  2.39 ( s , 3h ) , 7.36 ( d , j  =  8.0  hz , 2h ) , 7.507.62 ( m , 4h ) , 7.707.77 ( m , 3h ) , 8.088.14 ( m , 2h ) , 8.408.46 ( m , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  22.62 , 85.12 , 96.21 , 116.25 , 120.53 , 124.62 , 126.10 , 128.42 , 128.60 , 129.52 , 129.92 , 130.62 , 132.34 , 132.45 , 138.40 , 140.92 , 141.52 , 145.22 , 149.62  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  360 ( [ m ] , 100 ) , 345 ( 21 ) , 283 ( 64 ) , 259 ( 24 ) , 168 ( 22 ) ; hrms ( esi ) : m / z  =  360.1343 . white solid ; yield 304  mg ( 81  % ) ; m.p . : 250252  c ; rf  =  0.51 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,200 , 1,620  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  3.90 ( s , 3h ) , 7.20 ( d , j  =  8.7  hz , 2h ) , 7.417.52 ( m , 3h ) , 7.547.62 ( m , 3h ) , 7.677.70 ( m , 1h ) , 7.757.81 ( m , 2h ) , 8.06 ( d , j  =  8.4  hz , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  55.92 , 85.15 , 96.20 , 116.12 , 122.36 , 124.51 , 126.15 , 128.21 , 128.42 , 128.52 , 128.95 , 129.55 , 129.78 , 130.54 , 132.32 , 132.45 , 140.48 , 145.23 , 149.65  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  376 ( [ m ] , 100 ) , 345 ( 21 ) , 299 ( 64 ) , 275 ( 27 ) , 269 ( 32 ) , 168 ( 27 ) ; hrms ( esi ) : m / z  =  376.1360 . a mixture of 199  mg 2,3-dichloroquinoxaline ( 1.0  mmol ) , 0.1  cm hydrazine hydrate ( 99  % , 2.0  mmol ) , a suitable aldehyde ( 1.0  mmol ) , and 0.05  cm bromine ( 1.0  mmol ) were stirred in 5  cm h2o at room temperature under an argon atmosphere for 30  min . phenylacetylene ( 0.11  cm , 1  mmol ) , 53  mg pd / c ( 10  % , 0.05  mmol ) , and 276  mg k2co3 ( 2.0  mmol ) were added , and the resulting solution was heated at 70  c for 12  h , and then cooled to room temperature . the residue was purified by chromatography , eluting with chcl3/ch3oh ( 98:2 ) to afford the pure product ( table  2 ) . white solid ; yield 283  mg ( 82  % ) ; m.p . : 280282  c ; rf  =  0.53 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,200 , 1,650  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.327.42 ( m , 4h ) , 7.457.55 ( m , 4h ) , 7.67 ( d , j  =  4.8  hz , 1h ) , 7.81 ( d , j  =  4.1  hz , 1h ) , 7.867.92 ( m , 3h ) , 8.058.08 ( m , 1h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.26 , 96.37 , 123.80 , 127.55 , 127.85 , 128.11 , 128.21 , 128.70 , 128.95 , 129.22 , 129.55 , 129.76 , 130.45 , 132.10 , 132.45 , 138.92 , 142.17 , 145.11 , 149.12  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  346 ( [ m ] , 100 ) , 269 ( 52 ) , 245 ( 22 ) , 167 ( 16 ) ; hrms ( esi ) : m / z  =  346.1201 . white solid ; yield 367  mg ( 94  % ) ; m.p . : 284286  c ; rf  =  0.55 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,200 , 1,600 , 1,540 , 1,340  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.567.63 ( m , 3h ) , 7.737.75 ( m , 1h ) , 7.807.87 ( m , 3h ) , 7.95 ( dd , j  =  6.4 , 2.0  hz , 2h ) , 8.058.10 ( m , 2h ) , 8.168.19 ( m , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.39 , 96.45 , 121.36 , 122.72 , 127.45 , 128.25 , 128.35 , 128.47 , 128.66 , 129.42 , 129.58 , 129.68 , 131.36 , 132.45 , 132.60 , 135.54 , 142.36 , 145.78 , 149.25  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  391 ( [ m ] , 100 ) , 345 ( 32 ) , 314 ( 51 ) , 290 ( 21 ) , 169 ( 24 ) ; hrms ( esi ) : m / z  =  391.1037 . white solid ; yield 289  mg ( 74  % ) ; m.p . : 274276  c ; rf  =  0.52 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,230 , 1,610 , 1,530 , 1,340  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.28 ( s , 1h ) , 7.357.40 ( m , 2h ) , 7.467.52 ( m , 3h ) , 7.547.60 ( m , 3h ) , 7.647.71 ( m , 3h ) , 8.038.06 ( m , 1h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.26 , 96.35 , 121.10 , 122.45 , 127.52 , 128.45 , 129.26 , 129.45 , 129.64 , 129.88 , 130.20 , 131.36 , 132.25 , 132.45 , 142.36 , 145.56 , 148.92 , 149.55  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  391 ( [ m ] , 100 ) , 345 ( 35 ) , 314 ( 43 ) , 290 ( 26 ) , 167 ( 21 ) ; hrms ( esi ) : m / z  =  391.1042 . white solid ; yield 367  mg ( 94  % ) ; m.p . : 293295  c ; rf  =  0.54 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,210 , 1,620 , 1,540 , 1,320  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.40 ( d , j  =  8.4  hz , 1h ) , 7.557.61 ( m , 4h ) , 7.687.71 ( m , 1h ) , 7.807.86 ( m , 2h ) , 8.118.18 ( m , 3h ) , 8.55 ( d , j  =  8.2  hz , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  84.95 , 96.35 , 116.61 , 120.60 , 124.75 , 126.02 , 128.50 , 129.68 , 130.72 , 131.29 , 132.14 , 132.85 , 134.87 , 135.97 , 136.09 , 145.33 , 148.53 , 149.46  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  391 ( [ m ] , 100 ) , 345 ( 40 ) , 314 ( 47 ) , 290 ( 18 ) , 168 ( 29 ) ; hrms ( esi ) : m / z  =  391.1047 . white solid ; yield 276  mg ( 76  % ) ; m.p . : 305307  c ; rf  =  0.50 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,250 , 1,570  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.20 ( s , 1h ) , 7.357.43 ( m , 4h ) , 7.577.64 ( m , 4h ) , 7.827.86 ( m , 2h ) , 8.21 ( d , j  =  8.0  hz , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.80 , 96.42 , 116.62 , 122.26 , 122.92 , 124.85 , 127.70 , 128.37 , 128.81 , 129.21 , 130.35 , 130.56 , 133.51 , 133.65 , 141.52 , 146.23 , 146.56 , 149.55 , 160.42  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  364 ( [ m ] , 100 ) , 345 ( 27 ) , 287 ( 62 ) , 263 ( 42 ) , 167 ( 25 ) ; hrms ( esi ) : m / z  =  364.1152 . white solid ; yield 309  mg ( 85  % ) ; m.p . : 313315  c ; rf  =  0.51 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,230 , 1,590  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.20 ( s , 1h ) , 7.357.41 ( m , 2h ) , 7.557.62 ( m , 2h ) , 7.787.82 ( m , 2h ) , 7.907.98 ( m , 4h ) , 8.158.19 ( m , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.82 , 96.44 , 116.36 , 116.45 , 122.32 , 126.22 , 127.32 , 128.24 , 128.55 , 128.74 , 128.92 , 129.20 , 130.35 , 130.47 , 132.10 , 132.21 , 142.30 , 145.25 , 149.25 , 162.92  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  364 ( [ m ] , 100 ) , 345 ( 32 ) , 287 ( 67 ) , 263 ( 35 ) , 167 ( 29 ) ; hrms ( esi ) : m / z  =  364.1144 . white solid ; yield 315  mg ( 83  % ) ; m.p . : 276278  c ; rf  =  0.56 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,250 , 1,600  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.35 ( s , 1h ) , 7.437.52 ( m , 4h ) , 7.607.70 ( m , 4h ) , 8.068.12 ( m , 2h ) , 8.40 ( d , j  =  8.0  hz , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.65 , 96.53 , 123.42 , 127.53 , 127.65 , 128.21 , 128.32 , 128.42 , 128.65 , 129.25 , 129.64 , 130.36 , 130.54 , 132.25 , 132.36 , 132.46 , 138.65 , 142.35 , 145.65 , 149.58  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  382 ( [ m][cl ] , 31 ) , 380 ( [ m][cl ] , 100 ) , 345 ( 35 ) , 303 ( 57 ) , 279 ( 21 ) , 167 ( 25 ) ; hrms ( esi ) : m / z  =  380.0850 . white solid ; yield 326  mg ( 86  % ) ; m.p . : 289291  c ; rf  =  0.55 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,240 , 1,600  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.417.45 ( m , 1h ) , 7.557.63 ( m , 4h ) , 7.657.69 ( m , 1h ) , 7.717.77 ( m , 3h ) , 7.85 ( d , j  =  8.0  hz , 2h ) , 8.118.18 ( m , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.01 , 96.20 , 116.25 , 120.63 , 126.18 , 127.49 , 128.34 , 129.68 , 129.85 , 130.60 , 131.27 , 132.45 , 132.83 , 136.03 , 136.46 , 136.80 , 145.11 , 149.14  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  382 ( [ m][cl ] , 32 ) , 380 ( [ m][cl ] , 100 ) , 345 ( 30 ) , 303 ( 62 ) , 279 ( 26 ) , 168 ( 20 ) ; hrms ( esi ) : m / z  =  380.0850 . white solid ; yield 310  mg ( 75  % ) ; m.p . : 267269  c ; rf  =  0.57 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,210 , 1,620  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.20 ( s , 1h ) , 7.407.48 ( m , 4h ) , 7.557.62 ( m , 3h ) , 7.757.78 ( m , 2h ) , 8.128.15 ( m , 1h ) , 8.178.20 ( m , 1h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.35 , 96.23 , 127.80 , 127.95 , 128.44 , 128.84 , 128.92 , 129.10 , 129.25 , 129.54 , 130.92 , 131.44 , 132.35 , 132.74 , 133.55 , 138.22 , 142.62 , 145.84 , 149.12  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  418 ( [ m][cl2 ] , 12 ) , 416 ( [ m][cl][cl ] , 53 ) , 414 ( [ m][cl2 ] , 100 ) , 381 ( 23 ) , 339 ( 65 ) , 313 ( 30 ) , 269 ( 32 ) , 168 ( 15 ) ; hrms ( esi ) : m / z  =  414.0475 . : 218220  c ; rf  =  0.52 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,220 , 1,600  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  2.39 ( s , 3h ) , 7.36 ( d , j  =  8.0  hz , 2h ) , 7.507.62 ( m , 4h ) , 7.707.77 ( m , 3h ) , 8.088.14 ( m , 2h ) , 8.408.46 ( m , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  22.62 , 85.12 , 96.21 , 116.25 , 120.53 , 124.62 , 126.10 , 128.42 , 128.60 , 129.52 , 129.92 , 130.62 , 132.34 , 132.45 , 138.40 , 140.92 , 141.52 , 145.22 , 149.62  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  360 ( [ m ] , 100 ) , 345 ( 21 ) , 283 ( 64 ) , 259 ( 24 ) , 168 ( 22 ) ; hrms ( esi ) : m / z  =  360.1343 . white solid ; yield 304  mg ( 81  % ) ; m.p . : 250252  c ; rf  =  0.51 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,200 , 1,620  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  3.90 ( s , 3h ) , 7.20 ( d , j  =  8.7  hz , 2h ) , 7.417.52 ( m , 3h ) , 7.547.62 ( m , 3h ) , 7.677.70 ( m , 1h ) , 7.757.81 ( m , 2h ) , 8.06 ( d , j  =  8.4  hz , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  55.92 , 85.15 , 96.20 , 116.12 , 122.36 , 124.51 , 126.15 , 128.21 , 128.42 , 128.52 , 128.95 , 129.55 , 129.78 , 130.54 , 132.32 , 132.45 , 140.48 , 145.23 , 149.65  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  376 ( [ m ] , 100 ) , 345 ( 21 ) , 299 ( 64 ) , 275 ( 27 ) , 269 ( 32 ) , 168 ( 27 ) ; hrms ( esi ) : m / z  =  376.1360 . white solid ; yield 283  mg ( 82  % ) ; m.p . : 280282  c ; rf  =  0.53 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,200 , 1,650  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.327.42 ( m , 4h ) , 7.457.55 ( m , 4h ) , 7.67 ( d , j  =  4.8  hz , 1h ) , 7.81 ( d , j  =  4.1  hz , 1h ) , 7.867.92 ( m , 3h ) , 8.058.08 ( m , 1h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.26 , 96.37 , 123.80 , 127.55 , 127.85 , 128.11 , 128.21 , 128.70 , 128.95 , 129.22 , 129.55 , 129.76 , 130.45 , 132.10 , 132.45 , 138.92 , 142.17 , 145.11 , 149.12  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  346 ( [ m ] , 100 ) , 269 ( 52 ) , 245 ( 22 ) , 167 ( 16 ) ; hrms ( esi ) : m / z  =  346.1201 . white solid ; yield 367  mg ( 94  % ) ; m.p . : 284286  c ; rf  =  0.55 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,200 , 1,600 , 1,540 , 1,340  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.567.63 ( m , 3h ) , 7.737.75 ( m , 1h ) , 7.807.87 ( m , 3h ) , 7.95 ( dd , j  =  6.4 , 2.0  hz , 2h ) , 8.058.10 ( m , 2h ) , 8.168.19 ( m , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.39 , 96.45 , 121.36 , 122.72 , 127.45 , 128.25 , 128.35 , 128.47 , 128.66 , 129.42 , 129.58 , 129.68 , 131.36 , 132.45 , 132.60 , 135.54 , 142.36 , 145.78 , 149.25  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  391 ( [ m ] , 100 ) , 345 ( 32 ) , 314 ( 51 ) , 290 ( 21 ) , 169 ( 24 ) ; hrms ( esi ) : m / z  =  391.1037 . white solid ; yield 289  mg ( 74  % ) ; m.p . : 274276  c ; rf  =  0.52 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,230 , 1,610 , 1,530 , 1,340  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.28 ( s , 1h ) , 7.357.40 ( m , 2h ) , 7.467.52 ( m , 3h ) , 7.547.60 ( m , 3h ) , 7.647.71 ( m , 3h ) , 8.038.06 ( m , 1h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.26 , 96.35 , 121.10 , 122.45 , 127.52 , 128.45 , 129.26 , 129.45 , 129.64 , 129.88 , 130.20 , 131.36 , 132.25 , 132.45 , 142.36 , 145.56 , 148.92 , 149.55  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  391 ( [ m ] , 100 ) , 345 ( 35 ) , 314 ( 43 ) , 290 ( 26 ) , 167 ( 21 ) ; hrms ( esi ) : m / z  =  391.1042 . white solid ; yield 367  mg ( 94  % ) ; m.p . : 293295  c ; rf  =  0.54 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,210 , 1,620 , 1,540 , 1,320  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.40 ( d , j  =  8.4  hz , 1h ) , 7.557.61 ( m , 4h ) , 7.687.71 ( m , 1h ) , 7.807.86 ( m , 2h ) , 8.118.18 ( m , 3h ) , 8.55 ( d , j  =  8.2  hz , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  84.95 , 96.35 , 116.61 , 120.60 , 124.75 , 126.02 , 128.50 , 129.68 , 130.72 , 131.29 , 132.14 , 132.85 , 134.87 , 135.97 , 136.09 , 145.33 , 148.53 , 149.46  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  391 ( [ m ] , 100 ) , 345 ( 40 ) , 314 ( 47 ) , 290 ( 18 ) , 168 ( 29 ) ; hrms ( esi ) : m / z  =  391.1047 . white solid ; yield 276  mg ( 76  % ) ; m.p . : 305307  c ; rf  =  0.50 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,250 , 1,570  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.20 ( s , 1h ) , 7.357.43 ( m , 4h ) , 7.577.64 ( m , 4h ) , 7.827.86 ( m , 2h ) , 8.21 ( d , j  =  8.0  hz , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.80 , 96.42 , 116.62 , 122.26 , 122.92 , 124.85 , 127.70 , 128.37 , 128.81 , 129.21 , 130.35 , 130.56 , 133.51 , 133.65 , 141.52 , 146.23 , 146.56 , 149.55 , 160.42  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  364 ( [ m ] , 100 ) , 345 ( 27 ) , 287 ( 62 ) , 263 ( 42 ) , 167 ( 25 ) ; hrms ( esi ) : m / z  =  364.1152 . white solid ; yield 309  mg ( 85  % ) ; m.p . : 313315  c ; rf  =  0.51 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,230 , 1,590  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.20 ( s , 1h ) , 7.357.41 ( m , 2h ) , 7.557.62 ( m , 2h ) , 7.787.82 ( m , 2h ) , 7.907.98 ( m , 4h ) , 8.158.19 ( m , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.82 , 96.44 , 116.36 , 116.45 , 122.32 , 126.22 , 127.32 , 128.24 , 128.55 , 128.74 , 128.92 , 129.20 , 130.35 , 130.47 , 132.10 , 132.21 , 142.30 , 145.25 , 149.25 , 162.92  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  364 ( [ m ] , 100 ) , 345 ( 32 ) , 287 ( 67 ) , 263 ( 35 ) , 167 ( 29 ) ; hrms ( esi ) : m / z  =  364.1144 . white solid ; yield 315  mg ( 83  % ) ; m.p . : 276278  c ; rf  =  0.56 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,250 , 1,600  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.35 ( s , 1h ) , 7.437.52 ( m , 4h ) , 7.607.70 ( m , 4h ) , 8.068.12 ( m , 2h ) , 8.40 ( d , j  =  8.0  hz , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.65 , 96.53 , 123.42 , 127.53 , 127.65 , 128.21 , 128.32 , 128.42 , 128.65 , 129.25 , 129.64 , 130.36 , 130.54 , 132.25 , 132.36 , 132.46 , 138.65 , 142.35 , 145.65 , 149.58  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  382 ( [ m][cl ] , 31 ) , 380 ( [ m][cl ] , 100 ) , 345 ( 35 ) , 303 ( 57 ) , 279 ( 21 ) , 167 ( 25 ) ; hrms ( esi ) : m / z  =  380.0850 . white solid ; yield 326  mg ( 86  % ) ; m.p . : 289291  c ; rf  =  0.55 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,240 , 1,600  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.417.45 ( m , 1h ) , 7.557.63 ( m , 4h ) , 7.657.69 ( m , 1h ) , 7.717.77 ( m , 3h ) , 7.85 ( d , j  =  8.0  hz , 2h ) , 8.118.18 ( m , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.01 , 96.20 , 116.25 , 120.63 , 126.18 , 127.49 , 128.34 , 129.68 , 129.85 , 130.60 , 131.27 , 132.45 , 132.83 , 136.03 , 136.46 , 136.80 , 145.11 , 149.14  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  382 ( [ m][cl ] , 32 ) , 380 ( [ m][cl ] , 100 ) , 345 ( 30 ) , 303 ( 62 ) , 279 ( 26 ) , 168 ( 20 ) ; hrms ( esi ) : m / z  =  380.0850 . white solid ; yield 310  mg ( 75  % ) ; m.p . : 267269  c ; rf  =  0.57 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,210 , 1,620  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  7.20 ( s , 1h ) , 7.407.48 ( m , 4h ) , 7.557.62 ( m , 3h ) , 7.757.78 ( m , 2h ) , 8.128.15 ( m , 1h ) , 8.178.20 ( m , 1h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  85.35 , 96.23 , 127.80 , 127.95 , 128.44 , 128.84 , 128.92 , 129.10 , 129.25 , 129.54 , 130.92 , 131.44 , 132.35 , 132.74 , 133.55 , 138.22 , 142.62 , 145.84 , 149.12  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  418 ( [ m][cl2 ] , 12 ) , 416 ( [ m][cl][cl ] , 53 ) , 414 ( [ m][cl2 ] , 100 ) , 381 ( 23 ) , 339 ( 65 ) , 313 ( 30 ) , 269 ( 32 ) , 168 ( 15 ) ; hrms ( esi ) : m / z  =  414.0475 . white solid ; yield 288  mg ( 80  % ) ; m.p . : 218220  c ; rf  =  0.52 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,220 , 1,600  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  2.39 ( s , 3h ) , 7.36 ( d , j  =  8.0  hz , 2h ) , 7.507.62 ( m , 4h ) , 7.707.77 ( m , 3h ) , 8.088.14 ( m , 2h ) , 8.408.46 ( m , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  22.62 , 85.12 , 96.21 , 116.25 , 120.53 , 124.62 , 126.10 , 128.42 , 128.60 , 129.52 , 129.92 , 130.62 , 132.34 , 132.45 , 138.40 , 140.92 , 141.52 , 145.22 , 149.62  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  360 ( [ m ] , 100 ) , 345 ( 21 ) , 283 ( 64 ) , 259 ( 24 ) , 168 ( 22 ) ; hrms ( esi ) : m / z  =  360.1343 . white solid ; yield 304  mg ( 81  % ) ; m.p . : 250252  c ; rf  =  0.51 ; ir ( kbr ) : \documentclass[12pt]{minimal } 
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				 \begin{document}$$ \overline{\nu } $ $ \end{document }  =  2,200 , 1,620  cm ; h nmr ( 400  mhz , dmso - d6 ) :   =  3.90 ( s , 3h ) , 7.20 ( d , j  =  8.7  hz , 2h ) , 7.417.52 ( m , 3h ) , 7.547.62 ( m , 3h ) , 7.677.70 ( m , 1h ) , 7.757.81 ( m , 2h ) , 8.06 ( d , j  =  8.4  hz , 2h ) ppm ; c nmr ( 100  mhz , dmso - d6 ) :   =  55.92 , 85.15 , 96.20 , 116.12 , 122.36 , 124.51 , 126.15 , 128.21 , 128.42 , 128.52 , 128.95 , 129.55 , 129.78 , 130.54 , 132.32 , 132.45 , 140.48 , 145.23 , 149.65  ppm ; ms ( ei , 70  ev ) : m / z ( % )  =  376 ( [ m ] , 100 ) , 345 ( 21 ) , 299 ( 64 ) , 275 ( 27 ) , 269 ( 32 ) , 168 ( 27 ) ; hrms ( esi ) : m / z  =  376.1360 .
abstractcopper - free , pd / c - catalyzed , one - pot reaction of 2,3-dichloroquinoxaline with hydrazine hydrate , bromine , phenylacetylene , and a variety of aldehydes provides an efficient and direct method for the preparation of 1-aryl-4-(2-phenylethynyl)[1,2,4]triazolo[4,3-a]quinoxalines in water at 70  c . 
 this methodology involves the use of inexpensive reagents or catalysts , and thus permits a new and practical access to triazolo[4,3-a]quinoxalines.graphical abstract