Journal of Organic Chemistry p. 5660 - 5666 (1985)
Update date:2022-08-04
Topics:
Natale, N. R.
McKenna, John I.
Niou, Chorng-Shyr
Borth, Mark
Hope, Hakon
2-(5'-Alkylisoxazol-4'-yl)-Δ2-oxazoline was metalated at the C-5' alkyl group, and the lithio anion was quenched with a variety of electrophiles.Alkyl halides, aldehydes, and acylpyridinium salts were used as electrophiles.The lithio anion was oxygenated with MOOPH or N-(phenylsulfonyl)oxaziridene.The isoxazolyloxazoline system was converted to the isoxazolyl carboxylic acid, aldehyde, ketone, and chiral oxazoline.The isoxazolyloxazoline was formed, metalated, and deprotected in synthetically useful yields and represents a facile entry into functionally complex isoxazoles.To determine the necessity of the oxazoline protection/deprotection scheme, dianions of isoxazole-4-carboxylic acids were studied.The dianion method was found to be more efficient for simple alkyl halides, but limited in scope.
View MoreShandong Xiangde Biotechnology Co., Ltd
Contact:+86 -15066639877
Address:Sanba street
Hangzhou yi lu biont technology Co., LTD
Contact:+86-571-88152630
Address:Hangzhoushi HuafengRoad Yicheng3Building1001room.
Synochem Ingredients Corp., Ltd.
Contact:+86-512-5636 2180
Address:Zhangjiagang Free Trade Zone
Contact:+91 9963263336
Address:Plot#146A, IDA Mallapur, Hyderabad - 500072
Qingdao S. H. Huanyu Imp. & Exp. Co., Ltd.
Contact:86-532-88250866
Address:Room 615, World Trade Centre Building B, Hongkong Middle Roda 6#, Qingdao, Shandong, China
Doi:10.1248/cpb.26.2236
(1978)Doi:10.1021/jm00385a028
(1987)Doi:10.1021/ja00262a010
(1986)Doi:10.1021/jo00353a019
(1986)Doi:10.1039/jr9610004510
(1961)Doi:10.1021/jm00152a001
(1986)