Tetrahedron p. 1295 - 1310 (1990)
Update date:2022-08-05
Topics:
Bergman, Jan
Brynolf, Anna
Syntheses of both enantiomers of chrysogine, 2-(α-hydroxyethyl)-4(3H)-quinazolinone, 1 from 2-ammobenzamide are reported. Thus reaction of 2-aminobenzamide and optically active α-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)-1, using the Mitsunobo reaction, gave (+)-(R)-1. Reduction of 2-acetyl-4(3H)-qumazolinone 2 with baker's yeast gave the S-enantiomer of 1. The cyclization method used could be extended and a number of 2-(a-hydroxy)alkyl-4-(3H)-quinazolinones are also reported.
View MoreJinzhou Jiutai Pharmaceutical Co.,Ltd
Contact:+86-0416-5179890
Address:No.41, Taianli, Taihe District, Jinzhou, Liaoning
Baoding City Light Industry And Textiles Imp.& Exp. Corp. Chemical Department.
Contact:86-312-3262436
Address:NO.658 CHAOYANG SOUTH STREET,BAODING CITY HEBEI CHINA
Jiangsu Hualun Chemical Industry Co., Ltd
website:http://www.hualunchem.com
Contact:+86-0514-86464168 86507985
Address:39# Middle Renmin Road, Dinghuo Town
Contact:+86-21-61318535
Address:Building 29,No.2139 Xizha Road, Fengxian District, Shanghai
Contact:17316303296
Address:240 Amboy Ave
Doi:10.1002/poc.1328
(2008)Doi:10.1021/ja00398a016
(1981)Doi:10.1002/hlca.19560390629
(1956)Doi:10.1002/macp.1960.020360101
(1960)Doi:10.1038/sj.tpj.6500039
(1958)Doi:10.1021/ja01572a066
(1957)