Maqola

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

W. Russell BowmanDepartment of Chemistry, Loughborough University, Loughborough, Leics, UKM.R.J. ElsegoodDepartment of Chemistry, Loughborough University, Loughborough, Leics, UKTobias SteinDepartment of Chemistry, Loughborough University, Loughborough, Leics, UKGeorge W. WeaverDepartment of Chemistry, Loughborough University, Loughborough, Leics, UK

2006en

ABI

Annotatsiya

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 , mackinazolinone , tryptanthrin , luotonin A and rutaecarpine were synthesised by radical cyclisation onto 3H-quinazolin-4-one.

Identifikatorlar

DOI: 10.1039/b614075k

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