Brønsted Acid‐Promoted Cascade Alkylation/Cyclization of Pyrroles with N, N‐Dimethylaminomethyleneglutaconic Acid Dinitrile: A Concise Route to Cyclopenta[b]pyrroles. Issue 14 (11th September 2015)

• Record Type: Journal Article
• Authors: Wu, Kaikai; Wu, Ping; Chen, Jiping; Sun, Chenglin; Yu, Zhengkun
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 14/15(2015)
• Page Start: 3353
• Page End: 3358
• Publication Date: 2015-09-11
• Subjects: Brønsted acid -- cyclization -- cyclopenta[b]pyrroles -- N, N‐dimethylaminomethyleneglutaconic acid dinitrile -- pyrroles; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201500546
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A Brønsted acid ( p ‐TsOH⋅H2 O) promoted alkylation/cyclization cascade reaction of pyrroles with N, N ‐dimethylaminomethyleneglutaconic acid dinitrile was efficiently realized to afford functionalized cyclopenta[ b ]pyrroles with excellent diastereoselectivity. Deamination of the corresponding ammonium salts of the cyclopenta[ b ]pyrroles with methyl iodide led to dihydrocyclopenta[ c ]pyrroles. The cascade reaction pathway was confirmed by isolation and transformation of the reaction intermediate, i.e., the 2‐alkylated pyrrole. Abstract :