Tetrahedron letters

Flash vacuum pyrolysis of 1-allybenzotriazoles and dihydrobenzoxazines: Formation of quinolines

SJ Barker, GB Jones, KR Randles, RC Storr

Index: Barker, S. J.; Jones, G. B.; Randles, K. R.; Storr, R. C. Tetrahedron Letters, 1988 , vol. 29, # 8 p. 953 - 954

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Citation Number: 19

Abstract

1-Allylbenzotriazoles (l)l would appear to be potential precursors to quinolines since flash vacuum pyrolysis should lead to the diradical (2) which on intramolecular H transfer would give (3) and hence (7) by electrocyclisation and dehydrogenation. This is indeed the case; 1-allylbenzotriazole (1; R1 = R* = H) on flash pyrolysis at 75Qoc/lO-* torr gives quinoline in 46% yield. Unfortunately, the synthetic utility of the route is limited because alkyl substituents, R1 and ...