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Synthesis of Chrysogine, a Metabolite of Penicillium chrysogenum and some related 2-substituted 4-(3H)-Quinazolinones

โœ Scribed by Jan Bergman; Anna Brynolf

Book ID
104204138
Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
885 KB
Volume
46
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

Syntheses of both enantiomers of chrysogine. 2-(a-hydroxyethyl)4(3H)quinazolinone, 1 from 2aminobenzamide are reported. Thus reaction of 2aminobenxamide and optically active a-acetoxypropionyl chloride gave 9, which upon saponification and cyclization induced by aqueous sodium carbonate at room temperature gave chrysogine. The enantiomeric purity of 1 was determined by NMR. Inversion of (-)-(S>l. using the Mitsunobo maction. gave (+)-@Q-l. Reduction of 2-acetyL4(3H)quinazolinone 2 with baker's yeast gave the Senantiomer of 1. The cyclization method used could be extended and a number of 2-(a-hydroxy)alkyl-4-(3H)quinazolinones are also reported.

๐Ÿ“œ SIMILAR VOLUMES

Convenient synthesis of some 2-substitut
Convenient synthesis of some 2-substituted 4(3H)-quinazolinone derivatives
โœ I. Philipova; G. Dobrikov; K. Krumova; J. Kaneti ๐Ÿ“‚ Article ๐Ÿ“… 2006 ๐Ÿ› Journal of Heterocyclic Chemistry ๐ŸŒ English โš– 125 KB

## Abstract magnified image A series of 2โ€substitutedโ€4(3__H__)โ€quinazolinones **13โ€20** has been synthesized in good yields using the reaction of double lithiated 2โ€methylquinazolinoneโ€4 with a variety of aromatic aldehydes. They have been easily transformed in high yields into the corresponding