A simple Synthesis of the Debrominated Analogue of Veranamine. (February 2015)

• Record Type: Journal Article
• Authors: Liang, Dawei; Wang, Yueqiu; Wang, Yanyan; Di, Donghua
• Is Part Of: Journal of chemical research. Volume 39:Number 2(2015)
• Page Start: 105
• Page End: 107
• Publication Date: 2015-02
• Subjects: facile synthesis -- veranamine -- benzo[c][2, 7]naphthyridine -- 2-bromoaniline -- Sonogashira coupling; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.3184/174751915X14225441524178
• Languages: English
• ISSNs: 1747-5198

Abstract

A facile synthesis of 4, 5, 5-trimethyl-5, 6-dihydrobenzo[c][2, 7]naphthyridine, the debrominated analogue of the marine alkaloid veranamine, has been achieved in three steps with a 38% overall yield. from the commercially available 2-bromoaniline. The key benzo[c][2, 7]naphthyridine moiety was constructed using a Sonogashira coupling, a tandem Rupe rearrangement–Donnelly–Farrell cyclisation and a Diels–Alder reaction as the key steps. The synthetic strategy allows rapid access to various analogues of veranamine.