A Hofmann Rearrangement–Ring Expansion Cascade for the Synthesis of 1‐Pyrrolines: Application to the Synthesis of 2, 3‐Dihydro‐1H‐pyrrolo[2, 1‐a]isoquinolinium Salts. Issue 7 (19th February 2016)

• Record Type: Journal Article
• Authors: Huang, He; Yang, Qinghua; Zhang, Qianqian; Wu, Jie; Liu, Yizhen; Song, Chuanjun; Chang, Junbiao
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 7(2016)
• Page Start: 1130
• Page End: 1135
• Publication Date: 2016-02-19
• Subjects: 1‐pyrroline -- 2, 3‐dihydro‐1H‐pyrrolo[2, 1‐a]isoquinolinium salt -- cascade reaction -- cyclobutanecarboxamide -- rearrangement -- ring expansion; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201501071
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Treatment of cyclobutanecarboxamide with bis(trifluoroacetoxy)iodobenzene, PhI(OCOCF3 )2, resulted in the formation of 1‐pyrroline via Hofmann rearrangement of the former followed by in situ ring expansion reaction of the cyclobutylamine intermediate. Further elaboration of this methodology to the synthesis of 2, 3‐dihydro‐1 H ‐pyrrolo[2, 1‐ a ]isoquinolinium salts has also been described. Abstract :