Issue 20, 2011

Intramolecular Povarov reactions involving 3-aminocoumarins

Abstract

A series of pentacyclic heterocyclic systems (15 examples, 69–89%) have been synthesized using intramolecular Povarov reactions involving 3-aminocoumarins and O-cinnamylsalicylaldehydes. The Povarov adducts are formed with high selectivity for the trans,trans relative stereochemistry in the newly-formed [6,6] fused ring system. One example of a Povarov adduct featuring a new [6,5] fused ring system is reported. In this case, cis,trans relative stereochemistry was preferred.

Graphical abstract: Intramolecular Povarov reactions involving 3-aminocoumarins

Supplementary files

Article information

Article type
Paper
Submitted
01 Jun 2011
Accepted
18 Jul 2011
First published
20 Jul 2011

Org. Biomol. Chem., 2011,9, 7196-7206

Intramolecular Povarov reactions involving 3-aminocoumarins

A. A. Kudale, D. O. Miller, L. N. Dawe and G. J. Bodwell, Org. Biomol. Chem., 2011, 9, 7196 DOI: 10.1039/C1OB05867C

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