34774-96-4Relevant academic research and scientific papers
Benzo[c]isothiazole 2-Oxides: Three-Dimensional Heterocycles with Cross-Coupling and Functionalization Potential
Lamers, Philip,Buglioni, Laura,Koschmieder, Steffen,Chatain, Nicolas,Bolm, Carsten
, p. 3649 - 3653 (2016/11/25)
A robust method for the synthesis of benzo[c]isothiazole 2-oxides has been developed providing a range of functionalized derivatives starting from anilines and DMSO. The reaction sequence can be performed on a gram scale and leads to products that can easily be modified by standard cross-coupling reactions. (Figure presented.).
Formation of Sommelet-Hauser-Type Products, 2-Aminoarylmethyl Sulphides, and Nitrenium Ion Products, 2- and 4-Aminoaryl Sulphides, via an N-Arylazasulphonium Salt
Takeuchi, Hiroshi,Itou, Kazuaki,Murai, Hirotaka,Koyama, Kikuhiko
, p. 3156 - 3188 (2007/10/02)
Reactions of a salt (1) formed at -60 deg C from trifluoroacetic anhydride and dimethyl sulphoxide (DMSO) with primary and secondary arylamines gave 2-aminoarylmethyl sulphides (6), (6') and (12) by a Sommelet-Hauser rearrangement of an ylide (5) formed by loss of a methyl proton of an N-arylazasulphonium salt (3) in the absence of base.The use of ethyl methyl sulphoxide instead of DMSO afforded a similar product (19b) by loss of not the ethyl but the methyl proton.However, the use of diethyl sulphoxide merely caused loss of an ethyl group from the N-arylazasulphonium salt to yield ethanesulphenanilide (20).The reaction of (1) with N-phenyl-1-naphthylamine gave mainly aminoaryl sulphides (13) and (14) via an arylnitrenium ion from the N-arylazasulphonium salt.In fact, the reaction of dimethyl sulphide (DMS) with arylnitrenium ions formed in the acid decomposition of aryl azides gave no Sommelet-Hauser-type products but 2- and 4-aminoaryl sulphides (22), (22') and (23).We also discuss the possibility of the N-arylazasulphonium salt being formed by reaction of the arylnitrenium ion with DMS.
Thermal Reaction of Arylnitrenes with Dimethyl Sulphide, Thioanisole, and Tetrahydrothiophene
Benati, Luisa,Montevecchi, P. Carlo,Spagnolo, Piero
, p. 625 - 627 (2007/10/02)
The thermal decomposition of the aryl azides (1) into dimethyl sulphide (2), thioanisole (3), and tetrahydrothiophene (4) generally affords the 2-substituted anilines (5)-(7) in practicable yields by Sommelet-Hauser rearrangement of the intermediate N-arylsulphimides (11a-c) which result from arylnitrene attack at the sulphur atom of (2)-(4).This constitutes a potential synthetic procedure.
Process for preparing azasulfonium halide salts
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, (2008/06/13)
Preparing azasulfonium halide salt derivatives of an aniline by reacting a halogen with a non-carbonylic dihydrocarbon sulfide, a beta-carbonylic hydrocarbon sulfide, or a β-thio ester or amide to form a halogen: sulfur compound complex and then reacting the complex with an aniline to form the azasulfonium halide salts. The azasulfonium halide salts are useful as intermediates in processes for making ortho-alkylated anilines, indoles, and 2-oxindoles which have a variety of known uses.
