Alternative products in one-pot reaction of benzylidenemalononitrile,N-methyl-2-thiocarbamoylacetamide,and ω-bromoacetophenone |
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Authors: | A. Krauze M. Viļums L. Sīle G. Duburs |
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Affiliation: | (1) Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia |
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Abstract: | N-Methyl-2-benzoylmethylsulfanyl-4-phenylnicotinamide and N-methyl-2-(4-phenyl-1,3-thiazol-2-yl)-acetamide have been obtained as alternative products to the desired N-methyl-2,3-dihydro-7H-thiazolo[3,2-a]pyridine-8-carboxamide by a one-pot cyclocondensation of benzylidenemalononitrile, N-methyl-2-thiocarbamoylacetamide, piperidine, and ω-bromoacetophenone. 2-Amino-1-methyl-6-oxo-4-phenyl-5-(4-phenyl-1,3-thiazol-2-yl)-1,6-dihydropyridine-3-carbonitrile has been obtained as main product by treatment of benzylidenemalononitrile with N-methyl-2-(1,3-thiazol-2-yl)acetamide. Dedicated to Professor I. Kalvinsh on his 60th birthday __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 777–781, May, 2007. |
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Keywords: | 2-(benzoylmethylsulfanyl)nicotinamide 2,3-dihydro-7H-thiazolo[3,2-α ]pyridine-8-carboxamide N-methyl-2-(1,3-thiazol-2-yl)acetamide 6-oxo-5-(thiazol-2-yl)-1,6-dihydropyridine-3-carbonitrile |
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