By Moody C.J.
This quantity features a diversity of subject matters resembling the activation and manipulation of pyrroles, the synthesis of annelated pyrroles utilizing acylation reactions and the synthesis of kainoids, a kinfolk of hugely biologically energetic nitrogen heterocycles.
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Extra resources for Advances in Nitrogen Heterocycles, Volume 3
Ionization of Pyrrole-3-triflates . . . . . . . . C~ D. Pyrrolo[ 1,2-a]indoles . . . . . . . . . . . E. 7-Aminoaziridinomitosenes . . . . . . . . . Acknowledgments .......................... Reference and Notes . . . . . . . . . . . . . 83. Copyright 9 1998 by JAI Press Inc. All rights of reproduction in any form reserved. ISBN: 0-7623-0209-7 45 ...... 46 46 46 47 49 49 60 63 67 71 77 77 46 ERIC D. EDSTROM I. INTRODUCTION The efficient and regioselective synthesis of substituted pyrrole tings continues to be an important goal in organic synthesis.
As a result, the population of the 3,4-1q2 form is increased relative Osmium Activation of Pyrroles 27 to that for the unsubstituted pyrrole complex (20) to the point that cycloaddition becomes the dominant pathway, even for dipolarophiles as mild as methyl acrylate or acrylonitrile. 12,~4 To the extent that the enolate resulting from conjugate addition at the 13-carbon can be stabilized, the rate of this reaction pathway is enhanced. For example, 13-Michael additions are observed for MVK, acrolein, and acetylenic electrophiles even without the presence of a Lewis acid.
7 The further utility and extension of this acylative method for pyrrole synthesis had not been developed at the time our efforts commenced. ~R ~ I OH3 0 0 ~-N I CH3 R (3) 0 (4) B. General Scheme for Acylative Pyrrole Annulation In 1990 we initially became interested in the possibility of utilizing the acylative version of the Knorr pyrrole synthesis for the construction of pyrrolo[2,3-d]pyrimidines. Over the past 7 years this notion has been 48 ERIC D. E D S T R O M expanded into a useful strategy for the construction of several pyrroleannulated heterocyclic systems including pyrrolo[2,3-d]pyrimidines, 8a'g pyrrolo[ 1,2-c]pyridines, 8r imidazo[ 1,2-c]pyrimidin-3-ones, 8b 3,4-disubstituted indoles, 8f indole-4,7-quinones, and pyrrolo[1,2-a]indoles.