Regioselective Synthesis Of 3-Acylated Indolizines Using a Brederick-Type Reagent

T. Przewloka; S. Chen; Z. Xia; H. Li; S. Zhang; D. Chimmanamada; E. Kostik; D. James; K. Koya; L. Sun

doi:10.1055/s-2007-968972

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Synfacts 2007(10): 1034-1034
DOI: 10.1055/s-2007-968972

Synthesis of Heterocycles

Regioselective Synthesis Of 3-Acylated Indolizines Using a Brederick-Type Reagent

Contributor(s): Victor Snieckus, Jignesh J. Patel
T. Przewloka, S. Chen, Z. Xia, H. Li, S. Zhang, D. Chimmanamada, E. Kostik, D. James, K. Koya, L. Sun*
Synta Pharmaceuticals Corp., Lexington, USA

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Publication History

Publication Date:
07 November 2007 (online)

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Significance

A regioselective, reasonably efficient synthesis of 3-acylated indolizines by reaction of 2-picolinium salts with the modified Brederick-type reagent derived from DMF-Me₂SO₄ is reported. A small selection of functional groups was tolerated. This method provides the desired compounds of type A selectively in comparison with the product from the Chichibabin cyclocondensation product type B (A. E. Chichibabin, F. N. Stepanov Chem. Ber. 1929, 62B, 1068).