Intramolecular diels-alder reactions of 3H-pyrroles resulting from thermal rearrangements of 2H-pyrroles

A Eddaif, A Laurent, P Mison, N Pellissier…

Index: Eddaif, Abdelhamid; Laurent, Andre; Mison, Pierre; Pellissier, Nicole; Carrupt, Pierre-Alain; Vogel, Pierre Journal of Organic Chemistry, 1987 , vol. 52, # 25 p. 5548 - 5560

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Citation Number: 16

Abstract

The syntheses of methyl-and phenyl-substituted 2H-pyrroles 8 bearing a but-3-enyl or pent- 4-enyl side chain are reported. The thermolyses of 8 yielded tricyclic derivatives with the 2- azabicyclo [2.2. l] hept-2-ene moiety resulting from the intramolecular Diels-Alder additions of 3H-pyrrole intermediates. No product resulting from the intramolecular cycloaddition of 2H- pyrroles or of 1H-pyrroles was observed. Thermochemical analysis and ab initio STO-3G ...