Synthesis of thieno[2,3-b]quinoxalines from 2-haloquinoxalines

Journal of the Chemical Society. Perkin Transactions 1

Volumn , Issue 2, 2001, Pages 154-158

  Armengol, Montserrat ^a   Joule, John A ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CHEMICAL BONDS; DERIVATIVES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REDUCTION; SYNTHESIS (CHEMICAL); THIN LAYER CHROMATOGRAPHY;

CROSS COUPLING REACTIONS;

AROMATIC COMPOUNDS;

EID: 0035925018     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/b008459j     Document Type: Article

References (32)

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25. We thank the Nissan Chemical Company for a generous supply of 2,6-dichloroquinoxaline.
26. 4-Methoxyphenylethyne and 4-chlorophenylethyne were prepared via coupling of trimethylsilylacetylene with 4-methoxy- and 4-chloroiodobenzene respectively followed by desilylation (R. Liu and T.T. Tidwell, J. Chem. Soc., Perkin Trans. 2, 1996, 2757; G.T. Crisp and B.L. Flynn, J. Org. Chem., 1993, 58, 6614; E.-i. Negishi and T. Takahashi, J. Am. Chem. Soc., 1986, 108, 3402). 4-Nitro-and 3-nitrophenylethyne were prepared by condensation of the arylaldehyde with malonic acid, addition of bromine, and sequential eliminations of carbon dioxide and bromide and then hydrogen bromide (D.F. Delar, Org. Synth., 1963, Coll. Vol. IV, 731; C.P. Krimmel, L.E. Thielen, E.A. Brown and W.J. Heidtke, Org. Synth., 1962, Coll. Vol. IV, 961; E.R. Trumbull, R.T. Finn, K.M. Ibne-Rase and C.K. Saunders, J. Org. Chem., 1962, 27, 2343 (we found sodium hydrogen carbonate to be preferable to sodium hydroxide for the decarboxylative debromination); A.D. Allen and C.D. Cook, Can. J. Chem., 1963, 41, 1085). We thank Miss Mélanie Liutkus, a student from the University of Montpellier, France, for preparing the nitroarylethynes during a work experience period in Manchester.
27. 4-Methoxyphenylethyne and 4-chlorophenylethyne were prepared via coupling of trimethylsilylacetylene with 4-methoxy- and 4-chloroiodobenzene respectively followed by desilylation (R. Liu and T.T. Tidwell, J. Chem. Soc., Perkin Trans. 2, 1996, 2757; G.T. Crisp and B.L. Flynn, J. Org. Chem., 1993, 58, 6614; E.-i. Negishi and T. Takahashi, J. Am. Chem. Soc., 1986, 108, 3402). 4-Nitro-and 3-nitrophenylethyne were prepared by condensation of the arylaldehyde with malonic acid, addition of bromine, and sequential eliminations of carbon dioxide and bromide and then hydrogen bromide (D.F. Delar, Org. Synth., 1963, Coll. Vol. IV, 731; C.P. Krimmel, L.E. Thielen, E.A. Brown and W.J. Heidtke, Org. Synth., 1962, Coll. Vol. IV, 961; E.R. Trumbull, R.T. Finn, K.M. Ibne-Rase and C.K. Saunders, J. Org. Chem., 1962, 27, 2343 (we found sodium hydrogen carbonate to be preferable to sodium hydroxide for the decarboxylative debromination); A.D. Allen and C.D. Cook, Can. J. Chem., 1963, 41, 1085). We thank Miss Mélanie Liutkus, a student from the University of Montpellier, France, for preparing the nitroarylethynes during a work experience period in Manchester.
28. 4-Methoxyphenylethyne and 4-chlorophenylethyne were prepared via coupling of trimethylsilylacetylene with 4-methoxy- and 4-chloroiodobenzene respectively followed by desilylation (R. Liu and T.T. Tidwell, J. Chem. Soc., Perkin Trans. 2, 1996, 2757; G.T. Crisp and B.L. Flynn, J. Org. Chem., 1993, 58, 6614; E.-i. Negishi and T. Takahashi, J. Am. Chem. Soc., 1986, 108, 3402). 4-Nitro-and 3-nitrophenylethyne were prepared by condensation of the arylaldehyde with malonic acid, addition of bromine, and sequential eliminations of carbon dioxide and bromide and then hydrogen bromide (D.F. Delar, Org. Synth., 1963, Coll. Vol. IV, 731; C.P. Krimmel, L.E. Thielen, E.A. Brown and W.J. Heidtke, Org. Synth., 1962, Coll. Vol. IV, 961; E.R. Trumbull, R.T. Finn, K.M. Ibne-Rase and C.K. Saunders, J. Org. Chem., 1962, 27, 2343 (we found sodium hydrogen carbonate to be preferable to sodium hydroxide for the decarboxylative debromination); A.D. Allen and C.D. Cook, Can. J. Chem., 1963, 41, 1085). We thank Miss Mélanie Liutkus, a student from the University of Montpellier, France, for preparing the nitroarylethynes during a work experience period in Manchester.
29. 4-Methoxyphenylethyne and 4-chlorophenylethyne were prepared via coupling of trimethylsilylacetylene with 4-methoxy- and 4-chloroiodobenzene respectively followed by desilylation (R. Liu and T.T. Tidwell, J. Chem. Soc., Perkin Trans. 2, 1996, 2757; G.T. Crisp and B.L. Flynn, J. Org. Chem., 1993, 58, 6614; E.-i. Negishi and T. Takahashi, J. Am. Chem. Soc., 1986, 108, 3402). 4-Nitro-and 3-nitrophenylethyne were prepared by condensation of the arylaldehyde with malonic acid, addition of bromine, and sequential eliminations of carbon dioxide and bromide and then hydrogen bromide (D.F. Delar, Org. Synth., 1963, Coll. Vol. IV, 731; C.P. Krimmel, L.E. Thielen, E.A. Brown and W.J. Heidtke, Org. Synth., 1962, Coll. Vol. IV, 961; E.R. Trumbull, R.T. Finn, K.M. Ibne-Rase and C.K. Saunders, J. Org. Chem., 1962, 27, 2343 (we found sodium hydrogen carbonate to be preferable to sodium hydroxide for the decarboxylative debromination); A.D. Allen and C.D. Cook, Can. J. Chem., 1963, 41, 1085). We thank Miss Mélanie Liutkus, a student from the University of Montpellier, France, for preparing the nitroarylethynes during a work experience period in Manchester.
30. 4-Methoxyphenylethyne and 4-chlorophenylethyne were prepared via coupling of trimethylsilylacetylene with 4-methoxy- and 4-chloroiodobenzene respectively followed by desilylation (R. Liu and T.T. Tidwell, J. Chem. Soc., Perkin Trans. 2, 1996, 2757; G.T. Crisp and B.L. Flynn, J. Org. Chem., 1993, 58, 6614; E.-i. Negishi and T. Takahashi, J. Am. Chem. Soc., 1986, 108, 3402). 4-Nitro-and 3-nitrophenylethyne were prepared by condensation of the arylaldehyde with malonic acid, addition of bromine, and sequential eliminations of carbon dioxide and bromide and then hydrogen bromide (D.F. Delar, Org. Synth., 1963, Coll. Vol. IV, 731; C.P. Krimmel, L.E. Thielen, E.A. Brown and W.J. Heidtke, Org. Synth., 1962, Coll. Vol. IV, 961; E.R. Trumbull, R.T. Finn, K.M. Ibne-Rase and C.K. Saunders, J. Org. Chem., 1962, 27, 2343 (we found sodium hydrogen carbonate to be preferable to sodium hydroxide for the decarboxylative debromination); A.D. Allen and C.D. Cook, Can. J. Chem., 1963, 41, 1085). We thank Miss Mélanie Liutkus, a student from the University of Montpellier, France, for preparing the nitroarylethynes during a work experience period in Manchester.
31. 4-Methoxyphenylethyne and 4-chlorophenylethyne were prepared via coupling of trimethylsilylacetylene with 4-methoxy- and 4-chloroiodobenzene respectively followed by desilylation (R. Liu and T.T. Tidwell, J. Chem. Soc., Perkin Trans. 2, 1996, 2757; G.T. Crisp and B.L. Flynn, J. Org. Chem., 1993, 58, 6614; E.-i. Negishi and T. Takahashi, J. Am. Chem. Soc., 1986, 108, 3402). 4-Nitro-and 3-nitrophenylethyne were prepared by condensation of the arylaldehyde with malonic acid, addition of bromine, and sequential eliminations of carbon dioxide and bromide and then hydrogen bromide (D.F. Delar, Org. Synth., 1963, Coll. Vol. IV, 731; C.P. Krimmel, L.E. Thielen, E.A. Brown and W.J. Heidtke, Org. Synth., 1962, Coll. Vol. IV, 961; E.R. Trumbull, R.T. Finn, K.M. Ibne-Rase and C.K. Saunders, J. Org. Chem., 1962, 27, 2343 (we found sodium hydrogen carbonate to be preferable to sodium hydroxide for the decarboxylative debromination); A.D. Allen and C.D. Cook, Can. J. Chem., 1963, 41, 1085). We thank Miss Mélanie Liutkus, a student from the University of Montpellier, France, for preparing the nitroarylethynes during a work experience period in Manchester.
32. 4-Methoxyphenylethyne and 4-chlorophenylethyne were prepared via coupling of trimethylsilylacetylene with 4-methoxy- and 4-chloroiodobenzene respectively followed by desilylation (R. Liu and T.T. Tidwell, J. Chem. Soc., Perkin Trans. 2, 1996, 2757; G.T. Crisp and B.L. Flynn, J. Org. Chem., 1993, 58, 6614; E.-i. Negishi and T. Takahashi, J. Am. Chem. Soc., 1986, 108, 3402). 4-Nitro-and 3-nitrophenylethyne were prepared by condensation of the arylaldehyde with malonic acid, addition of bromine, and sequential eliminations of carbon dioxide and bromide and then hydrogen bromide (D.F. Delar, Org. Synth., 1963, Coll. Vol. IV, 731; C.P. Krimmel, L.E. Thielen, E.A. Brown and W.J. Heidtke, Org. Synth., 1962, Coll. Vol. IV, 961; E.R. Trumbull, R.T. Finn, K.M. Ibne-Rase and C.K. Saunders, J. Org. Chem., 1962, 27, 2343 (we found sodium hydrogen carbonate to be preferable to sodium hydroxide for the decarboxylative debromination); A.D. Allen and C.D. Cook, Can. J. Chem., 1963, 41, 1085). We thank Miss Mélanie Liutkus, a student from the University of Montpellier, France, for preparing the nitroarylethynes during a work experience period in Manchester.