34757-99-8Relevant academic research and scientific papers
Synthesis of 1,2-benzisothiazolin-3-one by transamination of sulfenamides
Shimizu, Masao,Takeda, Ayanobu,Fukazawa, Hidenori,Abe, Yoshimoto,Shibuya, Isao
, p. 1855 - 1864 (2007/10/03)
N-Substituted sulfenamoylbenzoates were synthesized by transamination of N-unsubstituted sulfenamoylbenzoates with amines. The reaction did not always proceed by simple amine exchange between the amines and ammonia on the sulfur atom of the sulfenamides. In reactions with aliphatic amines, the sulfenamides cyclized to form N-substituted 1,2-benzisothiazolin-3-ones. The synthesis of 1,2-benzisothiazolin-3-ones by intramolecular transamination was also investigated by S-amination of 2-mercaptobenzamides.
An effective synthesis of N-substituted 2-sulfenamoylbenzoates and 1,2-benzisothiazolin-3-ones that uses 1,2-benzisothiazolin-3-one as a leaving group
Shimizu, Masao,Sugano, Yoshinori,Konakahara, Takeo,Gama, Yasuo,Shibuya, Isao
, p. 3779 - 3783 (2007/10/03)
N-Substituted 2-sulfenamoylbenzoates and 1,2-benzisothiazolin-3-ones were effectively synthesized by the substitution reaction between S-[2-(3-oxo-1,2-benzisothiazolinyl)]-2-mercaptobenzoates (2) and primary amines. The substitution reaction occurred on the sulfur atom of the 2-sulfenamoyl group of 2, and 1,2-benzisothiazolin-3-one behaved as a leaving group. The eliminated 1,2-benzisothiazolin-3-one could be reused as a starting material for the synthesis of 2. N,N-Disubstituted 2-sulfenamoylbenzoates were prepared by the reaction of 2 with secondary amines.
