Tetrahedron p. 4329 - 4338 (1987)
Update date:2022-08-03
Topics:
Nasielski, J.
Heilporn, S.
Nasielski-Hinkens, R.
Geerts-Evrard, F.
Contrary to what is observed with other ?-deficient heteroaromatic N-oxides, the reaction of 2,3-diphenylquinoxaline-N1-oxide with OPCl3 gives only very poor yields of chlorinated quinoxalines.It is shown that the major product arises from an unprecedented attack by the nucleophilic oxygen atom of the reagent at a carbon atom of the homocycle of the O-phosphorylated N-oxide, leading ultimately to the corresponding mono- (or di-) aryl ester of phosphoric acid.Using a much smaller excess of OPCl3 and dilution of the medium with an inert solvent strongly increase the yield of chlorination products.It is suggested that, after the initial O-phosphorylation, phosphate formation might be the primary step in all the Meisenheimer reactions.
View MoreJinhua City Mingzhu Pharmaceutical Co.,Ltd.
Contact:15857995878 0579-82207761
Address:No.169 Shenze Road, New Area,Jinpan Development Zone, Jinhua
ZHANGJIAGANG FREE TRADE ZONE YONG HAN INTERNATIONAL TRADING CO., LTD(expird)
Contact:86 512 57910558
Address:qianjin M road
Contact:Tel: +86-25-58353800
Address:23 Lijing Road, Nanjing Hi-Tech Zone, Nanjing, Jiangsu, China, 210061
Zhuhai Rundu Pharmaceutical co.,Ltd
Contact:+86-756-7630755
Address:No.6,North Airport Road,Sanzao Town,Jinwan District
Shanghai Yingrui Biopharma Co., Ltd
Contact:021-3358 8661*8003
Address:shanghai
Doi:10.1002/anie.201002992
(2011)Doi:10.1080/00397910802604216
(2009)Doi:10.1021/ol900937f
(2009)Doi:10.1002/ejoc.201700463
(2017)Doi:10.1039/c3tc32035a
(2014)Doi:10.1002/ardp.19592920705
(1959)