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Report | Regular issue | Vol 12, No. 5, 1979, pp.695-697
Published online, 1st January, 1970
DOI: 10.3987/R-1979-05-0695
New Synthesis of Aminopropylbensenes and 1,2,3,4-Tetrahydroazocines from N-Substituted Tetrahydronicotinamides with Acetylenic Esters

R. Morrin Acheson and Giuseppe Paglietti*

*Instituto di Chimica Farmaceutica, University of Sassari, Via Muroni 23/a, 07100 Sassari, Italy

Abstract

Some N-substituted tetrahydronicotinamides (1) and dimethyl acetylenedicarboxylate (DMAD) gave the dienamines (3) through a known type of carboxamide elimination. However, these compounds further undergo cycloaddition to DMAD and via the intermediate (5) formed the aminopropylbenzenes (7-9) by a trans-elimination. In contrast (1b) with methyl propiolate, along with small amounts of dienamine (4) and aminopropylbenzene (10), gave in 40% yield the tetrahydroazocine (12), thus providing a new route to this class of heterocycles.