Domino reactions. One-pot preparation of fluoreno [2, 3, 4-ij] isoquinoline derivatives from conjugated ketene imines

…, A Vidal, J Fenau-Dupont, JP Declerq

Index: Molina, Pedro; Alajarin, Mateo; Vidal, Angel; Fenau-Dupont, J.; Declerq, J. P. Journal of Organic Chemistry, 1991 , vol. 56, # 12 p. 4008 - 4016

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Citation Number: 34

Abstract

Iminophosphoranes 4, derived from ethyl a-azido-2-(allyloxy)-3-methoxycinnamates, react with ketenes to give the corresponding ketene imines, which by thermal treatment at 150- 160 OC undeqo a consecutive electrocyclic ring cloeure/Claisen rearrangement/second ring cloeum/double aromatization proms to give boquinoline derivativea 7 and/or the previously unknown fluoreno [2, 3, 4-i~~ imquinolines 9 in moderate yields. S ily, ...