Tetrahedron

X Y ZH systems as potential 1, 3-dipoles. Part 36. 1, 5-Electrocyclisation processes via oxidation of tertiary amines. Pyrrolo-dihydroisoquinolines and-dihydro-β- …

R Grigg, P Myers, A Somasunderam, V Sridharan

Index: Grigg, Ronald; Myers, Peter; Somasunderam, Anoma; Sridharan, Visuvanathar Tetrahedron, 1992 , vol. 48, # 44 p. 9735 - 9744

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Citation Number: 30

Abstract

A range of tertiary N-allylamines derived from 1, 2, 3, 4-tetrahydroisoquinoline undergo oxidative cyclisation, induced by Ag2CO3, to pyrrolo-dihydroisoquinolines in moderate to good yield. Analogous oxidative cyclisations are reported for N-allyl-tetrahydro-β-carbolines and a pyrrolidine. The reactions proceed via formation of a 1, 5-dipole followed by an electrocyclisation and subsequent aromatisation.