Helvetica Chimica Acta p. 1305 - 1314 (1996)
Update date:2022-08-30
Topics:
Mlostoń, Grzegorz
Romański, Jaroslaw
Linden, Anthony
Heimgartner, Heinz
In order to trap 'thiocarbonyl-aminides' A, formed as intermediates in the reaction of thiocarbonyl compounds with phenyl azide, a mixture of 2,2,4,4-tetramethyl-3-thioxocyclobutanone (1), phenyl azide, and fumarodinitrile (8) was heated to 80° until evolution of N2 ceased. Two interception products of the 'thiocarbonylaminide' A (Ar = Ph) were formed: the known 1,4,2-dithiazolidine 3 (cf. Scheme 1) and the new 1,2-thiazolidine 12 (Scheme 2). The structure of the latter was established by X-ray crystallography (Fig. 1). The analogous 'three-component reaction' with dimethyl fumarate (9) yielded, instead of 8, in addition to the known interception products 3 and 6 (Scheme 1), two unexpected products 15 and 16 (Scheme 3), of which the structures were elucidated by X-ray crystallography (Fig. 2). Their formation is rationalized by a primary [2 + 3] cycloaddition of diazo compound 18 with 1 to give 19, followed by a cascade of further reactions (Scheme 4).
View MoreContact:+86-0311-84455288-844
Address:Mayu Industrial Park, Jinzhou, Hebei, China.
Weifang Yukai Chemical Co.,Ltd.
website:http://www.yukaichem.com/en.html
Contact:+86-536-8865336
Address:binhai economic development zone,262737 shangdong,china
Contact:+86-10-62651721
Address:29 Yongxing Road, Daxing District,Beijing China
Anhui Xinyuan Technology Co.,Ltd
website:http://www.ahxytech.com/
Contact:0086-559-3515800
Address:Huangshan City of Anhui Province Huizhou Huizhou District Road, 21-9
website:http://www.alwaychem.com
Contact:+86-532-8586-4000, 8586-5000
Address:NO.51, TAIPING ROAD, QINGDAO, CHINA. 266001
Doi:10.1006/jssc.2001.9126
(2001)Doi:10.1021/jacs.7b13189
(2018)Doi:10.1039/d1cc01072g
(2021)Doi:10.1021/np1009493
(2011)Doi:10.1016/j.chembiol.2020.12.004
(2021)Doi:10.1016/j.cclet.2015.12.005
(2016)