Synthesis of novel N-aroyl- and N-arylsulfonylisothiazole-2-imines by cyclization of thiocyanatovinylaldehyde hydrazones
New N-aroyl- and N-arylsulfonylisothiazole-imines are synthesized from thiocyanatovinylaldehyde and acceptor-substituted hydrazines.
References (15)
- et al.
Helv. Chim. Acta
(1991) - et al.
J. Prakt. Chem. Chem. Ztg.
(1992) Synthesis
(1973)Organ. Mass. Spectrom.
(1975)- et al.
J. Am. Chem. Soc.
(1979) J. Heterocycl. Chem.
(1968)- et al.
Indian J. Chem.
(1988)
Cited by (15)
Isothiazolium Salts and Their Use as Components for the Synthesis of S,N-Heterocycles
2007, Advances in Heterocyclic ChemistryCitation Excerpt :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.
The chemistry of isothiazoles
2003, TetrahedronCitation Excerpt :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.
Isothiazoles
1996, Comprehensive Heterocyclic Chemistry II: A Review of the Literature 1982-1995The first synthesis of an A-ring fused steroidal isothiazole
1994, Tetrahedron LettersFive-Membered Ring Systems: With N & S (Se) Atoms
1994, Progress in Heterocyclic Chemistry