A novel two-stage route to the 2a, 5a-diazacyclopenta [jk] fluorene ring system

AH Jackson, PVR Shannon, DJ Wilkins

Index: Jackson, Anthony; Shannon, Patrick V. R.; Wilkins, David J. Journal of the Chemical Society, Chemical Communications, 1987 , # 9 p. 653 - 654

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Abstract

The title ring system has been synthesised by phosphoryl chloride mediated cyclisation of the condensation product of tryptamine with diketene. ... In connection with studies' of the cyclisation of N-acyltrypt- amines to form spirocyclic systems related to indole alkaloids, we synthesised N-acetoacetyltryptamine (la), mp 77-78 "C, in 80% yield by treatment of tryptamine with diketene in tetrahydrofuran at 20°C for 2 h. Treatment of the amide (la) in dichloromethane with ...