Radical reactions with 3 H-quinazolin-4-ones: synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin

WR Bowman, MRJ Elsegood, T Stein…

Index: Bowman, W. Russell; Elsegood, Mark R. J.; Stein, Tobias; Weaver, George W. Organic and Biomolecular Chemistry, 2007 , vol. 5, # 1 p. 103 - 113

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Citation Number: 86

Abstract

Alkyl, aryl, heteroaryl and acyl radicals have been cyclised onto the 2-position of 3H- quinazolin-4-one. The side chains containing the radical precursors were attached to the nitrogen atom in the 3-position. The cyclisations take place by aromatic homolytic substitution hence retain the aromaticity of the 3H-quinazolin-4-one ring. The highest yields were obtained using hexamethylditin to facilitate cyclisation rather than reduction without ...