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

详细信息    查看全文

• 作者：He Huang ; Qinghua Yang ; Qianqian Zhang ; Jie Wu ; Yizhen Liu ; Chuanjun Song and Junbiao Chang
• 关键词：1-pyrroline ; 2 ; 3-dihydro-1H-pyrrolo[2 ; 1-a]isoquinolinium salt ; cascade reaction ; cyclobutanecarboxamide ; rearrangement ; ring expansion
• 刊名：Advanced Synthesis & Catalysis
• 出版年：2016
• 出版时间：March 31, 2016
• 年：2016
• 卷：358
• 期：7
• 页码：1130-1135
• 全文大小：408K
• ISSN：1615-4169

文摘

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-1H-pyrrolo[2,1-a]isoquinolinium salts has also been described.