One-pot synthesis of 3,4-disubstituted 1H-pyrroles from 2-tropanones



: Airaksinen AJ, Ahlgren M, Vepsalainen J

Publisher: AMER CHEMICAL SOC

: 2002

: Journal of Organic Chemistry

: JOURNAL OF ORGANIC CHEMISTRY

: J ORG CHEM

: 67

: 14

: 5019

: 5021

: 3

: 0022-3263

DOI: https://doi.org/10.1021/jo0257703


3,4-Disubstituted pyrroles (2, 3) were prepared from 6/7-carboxyethyl-3-phenyl-3-tropen-2-ones (1) regioselectively and with high yields by using tosylmethyl isocyanide (TosMIC). This procedure enables the synthesis of pyrroles substituted with two distinct groups: a phenyl group and a substituted pyrrolidine analogue. The crystal structure of product 2a was determined, and the analogous derivatives were identified by H-1 and C-13 NMR spectroscopy.



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