Synthesis of 5-oxo-1,2,3,5,6,7-hexahydroimidazo-[1,2-a]pyridine-8-carbonitriles, 6-oxo-2,3,4,6,7,8-hexahydro-1H-pyrido[1,2-a]pyrimidine-9-carbonitriles, and 7-oxo-1,2,3,4,5,7,8,9-octahydropyrido[1,2-a][1,3]diazepine-10-carbonitriles

Pedro Victory, Núria Busquets, JoséI I. Borrell, Jordi Teixidó, Carlos de Alvaro, Anna Arenas, Angel Alvarez-Larena, Joan F. Piniella

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5 Citations (Scopus)

Abstract

A simple method for the synthesis of the title compounds is described. Thus, α,β-unsaturated esters (1) are transformed in the already described 2-methoxy-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitriles (3) which are treated with NH2(CH2)nNH2 (n = 2, 3, 4) to afford the corresponding bicyclic compounds (4, 5, and 6). The nitrogen bridged nature of these compounds is determined by an X-ray structure analysis of 4b. A ring opening-ring closure mechanism is proposed for the formation of structures (4-6) on the basis of the reaction between 3b and 15N,15N′-ethylenediamine which afforded 15N,15N′-4b. © 1995.
Original languageEnglish
Pages (from-to)2173-2179
JournalHeterocycles
Volume41
Issue number10
Publication statusPublished - 1 Oct 1995

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