Issue 1, 2007
From the journal:

Organic & Biomolecular Chemistry

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

W. Russell Bowman,*a   Mark R. J. Elsegood,a   Tobias Steina  and  George W. Weaver*a  

* Corresponding authors

a Department of Chemistry, Loughborough University, Loughborough, Leics, UK
E-mail: g.w.weaver@lboro.ac.uk
Fax: 44(0) 1509 223925
Tel: 44(0) 1509 222584

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 cyclisation. The alkaloids deoxyvasicinone 2, mackinazolinone 3, tryptanthrin 4, luotonin A 5 and rutaecarpine 8 were synthesised by radical cyclisation onto 3H-quinazolin-4-one.

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

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Article information

DOI
https://doi.org/10.1039/B614075K
Article type
Paper
Submitted
27 Sep 2006
Accepted
19 Oct 2006
First published
03 Nov 2006

Org. Biomol. Chem., 2007,5, 103-113

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

W. R. Bowman, M. R. J. Elsegood, T. Stein and G. W. Weaver, Org. Biomol. Chem., 2007, 5, 103 DOI: 10.1039/B614075K

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