1701-95-7Relevant articles and documents
Radical reactions with 3H-quinazolin-4-ones: Synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin
Bowman, W. Russell,Elsegood, Mark R. J.,Stein, Tobias,Weaver, George W.
, p. 103 - 113 (2008/03/14)
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. This journal is The Royal Society of Chemistry.
HETEROCYCLIZATION WITH IMINIUM CHLORIDES, II. SYNTHESIS OF 4H--BENZOXAZINE-4-ONES AND QUINAZOLINONES
Bitter, I.,Szoecs, L.,Toeke, L.
, p. 57 - 66 (2007/10/02)
Reactions between methyl anthranilate and a variety of PI salts afforded 2-ammonio-4H--benzoxazine-4-one chlorides which were subjected to nucleophilic reactions.With primary amines, 2-ureidoanthraniloyl amides were obtained, which were smoothly cyclized in boiling acetic anhydride or dimethylformamide to give 1H,3H-quinazoline-2,4-diones.