Journal of the Chemical Society. Perkin transactions I p. 1047 - 1055 (1996)
Update date:2022-07-29
Topics:
Atkinson, Robert S.
Barker, Emma
Edwards, Paul J.
Thomson, Gordon A.
3-Diacylaminoquinazolinones 10 and 15 have high enough barriers to rotation around their N-N bonds to allow separation of each into diastereoisomers. Interconversion of diastereoisomers 10a and 10b occurs on heating in boiling toluene and thermodynamic parameters for this process have been measured. The barriers to rotation around the N-N bonds in analogous monoacylaminoquinazolinones are not sufficient to permit isolation of stereoisomers at room temperature unless the exocyclic nitrogen is additionally substituted e.g. by an alkyl group as in 28. X-Ray crystal structure determinations carried out on 10a, 10b, 15a and 28b confirm the presence of chiral axes. Reaction of both diastereoisomers 15a and 15b with 1-phenylethylamine takes place with exclusive reaction at the 1-acetoxypropionyl carbonyl group and with partial kinetic resolution: the preferred sense of enantioselectivity obtained is dominated by the N-N axis.
View MoreShanghai Sharing technologies Co., Ltd.
Contact:86-021-66787223
Address:No11, Lane 225, Jinxiang Road,Pudong district
Contact:+86-15850770348
Address:51 OF XIANGFANGCUN ROAD, Nanjing 210002, China
Anhui Biochem United Pharmaceutical Co., Ltd.
Contact:0086 551 5167062 / 5228268
Address:No. 30 Hongfeng Road, Hi-Tech Development Zone, Hefei (230088), China
Jiangsu Hualun Chemical Industry Co., Ltd
website:http://www.hualunchem.com
Contact:+86-0514-86464168 86507985
Address:39# Middle Renmin Road, Dinghuo Town
website:https://www.sinoshiny.com/products
Contact:+86-20-62802632;62802633
Address:Room 330 GIGCAS Building,No.511 Kehua Street,Tianhe District
Doi:10.1021/jm9705770
(1998)Doi:10.1007/BF01165911
(1996)Doi:10.1016/j.tet.2005.03.066
(2005)Doi:10.1039/P19960002061
(1996)Doi:10.1002/(SICI)1099-1344(199608)38:8<725::AID-JLCR885>3.0.CO;2-G
(1996)Doi:10.1016/S0960-894X(96)00265-X
(1996)
