New synthesis of 2,2 '-heteroarylpyrroles from ...



Title New synthesis of 2,2 '-heteroarylpyrroles from heteroarylchlorocarbenes
Author(s) Y. N. Romashin, Michael T. H. Liu, W. Ma, R. A. Moss
Journal Tetrahedron Letters
Date 1999
Volume 40
Issue 40
Start page 7163
End page 7165
Abstract 2,2'-Pyridyl- and 2,2'-thienylpyrroles containing substituents at the 1- and 3-positions of the pyrrole ring have been prepared from the reaction of heteroarylchlorocarbenes with 1-azabuta-1,3-dienes. Laser flash photolysis of heteroarylchlorocarbene in isooctane in the presence of 1-azabuta-1,3-diene yields an azomethine ylide (lambda=550 nm) as an intermediate. The kinetic parameters for the ylide formation and further 1,5-intramolecular cyclization to the pyrrole ring have been determined. (C) 1999 Elsevier Science Ltd. All rights reserved.

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