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Paper | Regular issue | Vol 41, No. 10, 1995, pp.2173-2179
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7051
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, José I. Borrell,* Jordi Teixidó, Carlos de Alvaro, Anna Arenas, Angel Alvarez-Larena, and Joan F. Piniella

*Departament de Química Orgànica, CETS Institut Químic de Sarrià , Universitat Ramon Llull, E-08017 Barcelona, Spain


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 is determined by an X-ray structure analysis of 4a. 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.