Tandem transformations of 10-substituted tetrahydrobenzo[b][1,6]naphthyridines resulted from the Michael addition of the nitrogen atom of the tetrahydropyridine fragment to the triple bond of activated alkynes |
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Authors: | L. G. Voskressensky T. N. Borisova I. V. Vorob’ev N. M. Postika E. A. Sorokina A. V. Varlamov |
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Affiliation: | (1) Peoples’ Friendship University of Russia, 6 ul. Miklukho-Maklaya, 117198 Moscow, Russian Federation |
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Abstract: | A reaction of 10-R-substituted tetrahydrobenzo[b][1,6]naphthyridines (R = CN, CONH2, Me) with dimethyl acetylenedicarboxylate, methyl and ethyl propiolates, and acetylacetylene has been studied. It was found that 1-acryloyl-10-cyanotetrahydrobenzo[b][1,6]naphthyridines are the major products of the reaction of alkyl propiolates with 10-cyano-substituted naphthyridines, whereas the reaction with 10-carbamoyl-substituted naphthyridines gives a mixture of 1-acryloyl-substituted naphthyridines and hexahydrobenzo[b]pyrido[3,4,5-d,e][1,6]naphthyridines. The latter are the only products in the reaction of 10-carbamoyl-substituted naphthyridines with acetylacetylene. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1516–1527, July, 2008. |
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Keywords: | alkynes the Michael reaction benzo[b][1,6]naphthyridines benzo[b]pyrido-[3,4,5-d,e][1,6]naphthyridines |
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