New Journal of Chemistry p. 9373 - 9376 (2018)
Update date:2022-08-05
Topics:
Il'In, Mikhail V.
Bolotin, Dmitrii S.
Suslonov, Vitalii V.
Kukushkin, Vadim Yu
The reaction of aminonitrones R1C(NH2) = N+(Me)O- (R1 = Alk, Ar) with isocyanides R2NC (R2 = Alk, Ar; 1.2 equiv.) and Br2 (1 equiv.) conducted in CHCl3 (RT, 5 min) gives 2-methyl-5-amino-1,2,4-oxadiazolium bromides in good to excellent yields (65-95%; 16 examples). These species are highly electrophilically activated and 5-cyclohexylamino-2-methyl-3-phenyl-1,2,4-oxadiazolium bromide, taken as a model compound for the reactivity study, reacts rapidly under mild conditions with hydroxylamine, hydrazine, or benzamidine, to give 5-cyclohexylamino-3-phenyl-1,2,4-oxadiazole (88%), 5-cyclohexylamino-3-phenyl-1,2,4-triazole (95%), and 2-cyclohexylamino-4,6-diphenyl-1,3,5-triazine (64%), respectively. Treatment of the oxadiazolium salt with excess water provides N-benzoyl-N′-cyclohexylurea (95%).
View MoreHubei Xinghuo Chemical Co., Ltd.,
Contact:13925817279 13907299441
Address:Xinghuo Fine Chemistry Industrial Park, Xiaochang County, Hubei Province, China
website:http://www.lonwinchem.com
Contact:Tel: 86-21-59858395
Address:No#966,Huaxu Road,Shanghai 201702,P.R.China
Zhejiang Rongkai Chemical Technology Co.,Ltd.
Contact:+86-578-8185786
Address:Shangjiang Industrial Zone,Suichang
Changyi Xinxing Technology Development Co., Ltd.
Contact:0086-510-86651065(Time Zone:8),86651656
Address:94 Yingbinxilu WestRoad, Huangtu Town, Jiangyin City, Jiangsu, China
Contact:86-21-50966856
Address:Building 5,300 Chuanzhan Road,Pudong New District,Shanghai
Doi:10.1021/jo00918a028
(1974)Doi:10.1002/jlcr.893
(2005)Doi:10.1002/ejoc.202000151
(2020)Doi:10.1007/s007060170009
(2001)Doi:10.1016/S0008-6215(00)81314-2
(1973)Doi:10.1021/ja00798a027
(1973)