Preparations of diversely substituted thiosemicarbazides and N-hydroxythioureas

Abstract

Thiosemicarbazides 5 (yields 50-97%) and N-hydroxythioureas 6 (yields 71-99%) of variable substitution patterns are prepared efficiently by reactions of 1-(thiocarbamoyl)benzotriazoles 4a-i with hydrazines or hydroxylamines, respectively.

C-Aminoimidoylation and C-Thiocarbamoylation of Esters, Sulfones, and Ketones

“…Recently, we synthesized (i) 1,2,3-trisubstituted guanidines, N- hydroxy-, and N- amino-guanidines using novel benzotriazole-1-carboxamidine N -aminoimidoylating reagents (Scheme ), and (ii) di- and trisubstituted thioureas, N -hydroxythioureas, and thiosemicarbazides using novel 1-(alkyl/arylthiocarbamoyl)benzotriazole thiocarbamoylating reagents (Scheme ). In the present paper, we demonstrate that esters, sulfones, and ketones can be C-aminoimidoylated by benzotriazole-1-carboxamidines 8a − g and C-thiocarbamoylated by 1-(alkyl/arylthiocarbamoyl)benzotriazoles 9a − i.…”

Bis(benzotriazolyl)methanethione

“…7 (E) Thiosemicarbazides and N-hydroxythioureas of diverse substitution patterns have also been synthesized using bis(benzotriazole-1-yl)methanethione as a precursor by reaction of the appropriate hydrazine and corresponding hydroxylamine, respectively. 8 (F) The Diels-Alder addition of bis(benzotriazole-1-yl)methanethione to cyclopentadiene provides the moisture-stable crystalline adduct. 9 (G) Katritzki et al have reported the synthesis of acyclic and cyclic 1,2,3-trisubstituted guanidines 10 in high yield with a convenient method for the guanylation of various primary and secondary amines by the use of (bisbenzotriazol-1-yl-methylene)amines and benzotriazole-1-carboxamidines.…”

Tetracyanoethylene as a building block in the facile synthesis of heteroyl-tetrasubstituted thiazoles

“…Due to the accessibility and ability of carbothioamides and their analogs to act as bifunctional nucleophiles [1][2][3][4][5][6], they play a significant role among other nitrogen and sulfur-containing compounds.…”