Synthesis of novel N-aroyl- and N-arylsulfonylisothiazole-2-imines by cyclization of thiocyanatovinylaldehyde hydrazones

doi:10.1016/S0040-4039(00)91960-9

Tetrahedron Letters

Volume 34, Issue 12, 19 March 1993, Pages 1909-1912

https://doi.org/10.1016/S0040-4039(00)91960-9 Get rights and content

Abstract

The synthesis of N-aroyl- and N-arylsulfonylisothiazole-2-imines 7c-f as well as the corresponding acceptor-substituted 2-aminoisothiazolium sa

New N-aroyl- and N-arylsulfonylisothiazole-imines are synthesized from thiocyanatovinylaldehyde and acceptor-substituted hydrazines.

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The reaction of 2-aryl-5,6-dihydro-4H-cyclopenta[d]isothiazolium perchlorates 122 (n=0) with anilines produced in nearly quantitative yields (95–99%) only vinamidines 128 (n=0) as the main products of sufficient purity (00JPR675). β-Thiocyanatovinylaldehydes 119 were also versatile C3S building blocks in the synthesis of acceptor substituted 2-amino-isothiazolium salts 131 and 132 by intramolecular cyclocondensation of thiocyanatovinylaldehyde hydrazones 129 (93TL1909). The alternative cyclization route to 1,2,3-thiadiazines was not observed.
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2003, Tetrahedron
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Saccharin and other derivatives of isothiazole-1,1-dioxide do not comply with the normal (4n+2)π-electron rule for aromaticity, but in view of the fact that they have been shown earlier to have a degree of π-electron delocalisation through the sulfur atom, and for convenience of classification of their chemical reactions, they are considered to be aromatic in the subsequent sections dealing with their chemistry. The aromaticity of the heterorings containing N, S and/or O was studied from crystallographic structure data (CSD) of some isothiazole derivatives.17,18 The polychloronitrodiene 5 gave 3-trichloromethyl-4,5-dichloroisothiazole 6 on heating strongly with neat sulphur.
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Synthesis of novel N-aroyl- and N-arylsulfonylisothiazole-2-imines by cyclization of thiocyanatovinylaldehyde hydrazones

Abstract

Helv. Chim. Acta

J. Prakt. Chem. Chem. Ztg.

Synthesis

Organ. Mass. Spectrom.

J. Am. Chem. Soc.

J. Heterocycl. Chem.

Indian J. Chem.