Reactions of the activated, rigid, α-diazomethine group of 1,2,5-thiadiazole 1,1-dioxides with nitrogenated nucleophiles. Part III: aliphatic monoamines and phenylhydrazine
作者:José Alberto Caram、Oscar Enrique Piro、Eduardo Ernesto Castellano、María Virginia Mirífico、Enrique Julio Vasini
DOI:10.1002/poc.1022
日期:2006.4
forming the corresponding thiadiazolines in an equilibrium monoaddition reaction. The equilibrium constants were evaluated and compared. With primary amines and PhN2H3, the nucleophile added to both CN double bonds of 1a and displaced the sulfamide moiety. In the case of the reaction of 1a with PhN2H3, the intermediate monoaddition thiadiazoline, 3-(2-phenylhydrazino)-3,4-diphenyl-1,2,5-thiadiazoline 1,1-dioxide
的反应Ñ丁胺(BuNH 2),2-氨基乙醇(H 2 N(CH 2)2 OH),二乙胺(ET 2 NH),和苯(PHN 2 ħ 3)与3,4-二苯基- (1A),并在非质子溶剂溶液中通过循环伏安法(CV)和1 H-和13 C-NMR研究了菲咯啉[9,10-c] -1,2,5-噻二唑1,1-二氧化物(1b)。反应过程取决于底物-亲核试剂的组合:将Et 2 NH添加到1a或1b中,在平衡单加成反应中形成相应的噻二唑啉。评估并比较平衡常数。用伯胺和PhN 2 H 3,亲核试剂加到1a的两个C N双键上,并取代了磺酰胺部分。在1a与PhN 2 H 3反应的情况下,还分离出中间体单加成噻二唑啉3-(2-苯基肼基)-3,4-二苯基-1,2,5-噻二唑啉1,1-二氧化物。BuNH 2和H 2 N(CH 2)2 OH与1a反应生成α-双亚胺,而1a与PhN反应2 H 3得到α-双bis。通过单晶X射线衍射分