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.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1516–1527, July, 2008.
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Voskressensky, L.G., Borisova, T.N., Vorob’ev, I.V. et al. 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. Russ Chem Bull 57, 1547–1558 (2008). https://doi.org/10.1007/s11172-008-0200-y
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DOI: https://doi.org/10.1007/s11172-008-0200-y