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Synthesis 2004(6): 918-922
DOI: 10.1055/s-2004-815976
DOI: 10.1055/s-2004-815976
PAPER
© Georg Thieme Verlag Stuttgart · New York
Allylated β-Ketoesters as Precursors in Paal-Knorr-Type Pyrrole Synthesis: Preparations of Chiral and Bispyrroles
Further Information
Received
7 January 2004
Publication Date:
12 February 2004 (online)
Publication History
Publication Date:
12 February 2004 (online)
Abstract
A simple and facile preparation of chiral and bis-pyrroles is described here. This method involves a modified Paal-Knorr reaction using 1,4-dicarbonyl systems derived from ozonolysis of allylated β-ketoester.
Key words
Paal-Knorr synthesis - chiral and bispyrroles - ozonolysis - allylated β-ketoester
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References
Solvents such as MeOH, CH3CN, THF, EtOAc, CH2Cl2, and toluene were screened with CH3CN giving the highest yield and cleanest products as determined by LCMS. The reactions were also run at r.t., 50 °C, and 80 °C to determine the optimal temperature. A variety of acids such as aq HCl and aq H2SO4were screened in addition to p-TsOH.