Journal of Organic Chemistry p. 4056 - 4071 (2017)
Update date:2022-08-05
Topics:
Filimonov, Valeriy O.
Dianova, Lidia N.
Galata, Kristina A.
Beryozkina, Tetyana V.
Novikov, Mikhail S.
Berseneva, Vera S.
Eltsov, Oleg S.
Lebedev, Albert T.
Slepukhin, Pavel A.
Bakulev, Vasiliy A.
High yield solvent-base-controlled, transition metal-free synthesis of 4,5-functionalized 1,2,3-thiadiazoles and 1,2,3-triazoles from 2-cyanothioacetamides and sulfonyl azides is described. Under diazo transfer conditions in the presence of a base in an aprotic solvent 2-cyanothioacetamides operating as C-C-S building blocks produce 5-amino-4-cyano-1,2,3-thiadiazoles exclusively. The use of alkoxide/alcohol system completely switches the reaction course due to the change of one of the reaction centers in the 2-cyanothioacetamide (C-C-N building block) resulting in the formation of 5-sulfonamido-1,2,3-triazole-4-carbothioamide sodium salts as the only products. The latter serve as good precursors for 5-amino-1,2,3-thiadiazole-4-carboximidamides, the products of Cornforth-type rearrangement occurring in neutral protic medium or under acid conditions. According to DFT calculations (B3LYP/6-311+G(d,p)) the rearrangement proceeds via intermediate formation of a diazo compound, and can be catalyzed by acids via the protonation of oxygen atom of the sulfonamide group.
View MoreWuxi Morality Chemical Co., Ltd(expird)
Contact:
Address:B/7F, 321th WuYun Rd, Wanda Plaza, Wuxi City, 214174, China
Wuxi Morality Chemical Co., Ltd(expird)
Contact:
Address:B/7F, 321th WuYun Rd, Wanda Plaza, Wuxi City, 214174, China
Shijiazhuang City Xiehe Pharmaceutical Co., Ltd
Contact:+86-311-80817929
Address:Shangzhuang,Shijiazhuang,China
Tianjin Bright Future Technology Co., Ltd
Contact:0086-22-58016666
Address:NO.136 DongTeng Lake Street Tianjin Economic and Technology Development Area,Tainjin,China
Rugao Jinling Chemical Co., Ltd.(expird)
Contact:0086-513-68005586
Address:Lianluo new village huangshi town Rugao city Jiangsu Province.
Doi:10.1016/S0040-4039(00)97519-1
(1982)Doi:10.1016/0277-5387(94)00355-I
(1995)Doi:10.1021/ja01167a602
(1950)Doi:10.2533/000942904777677524
(2004)Doi:10.1016/j.carres.2007.07.011
(2007)Doi:10.1016/S0040-4020(01)92855-8
(1970)