Tetrahedron

The intramolecular 1, 3-dipolar cyclisation of mesoionic species generated by the thermolysis of the mixed anhydrides of acetic and N-alkynoyl-1, 2, 3, 4- …

M Sainsbury, RH Strange, PR Woodward, PA Barsanti

Index: Sainsbury, Malcolm; Strange, Rosalind H.; Woodward, Peter R.; Barsanti, Paul A. Tetrahedron, 1993 , vol. 49, # 10 p. 2065 - 2076

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Citation Number: 10

Abstract

The intramolecular cyclisations of mesoionic intermediates formed by heating N-alkynoyl-1, 2, 3, 4-tetrahydroisoquinoline-3-carboxylic acids [alkylnoyl side chains: RC C-(CH2) 2CO, where n= 3 or 4] with acetic anhydride, have been investigated. The final products are octahydropentaleno [2, 3-a] isoquinolines and hexahydroindeno [2, 3-a] isoquinolines respectively, formed by the expulsion of carbon dioxide from the initial adducts. The ...