Isothiazoles (1,2-thiazoles): synthesis, properties and applications

Abstract

The most recent achievements in the chemistry of The most recent achievements in the chemistry of isothiazoles are generalised and systematised. The main applica-isothiazoles are generalised and systematised. The main applications of isothiazole derivatives are surveyed. The bibliography tions of isothiazole derivatives are surveyed. The bibliography includes 293 references includes 293 references. .

Complete 1H and 13C NMR spectral assignment of benzo[d]isothiazole derivatives and of an isoindole isoster

“…After refluxing for 2 h, the reaction mixture was cooled, and then the solvent was removed under reduced pressure. The residue was extracted with CH 2 Cl 2 , washed with 2 N HCl, and then dried over Na 2 …”

“…For a number of years, we have designed, synthetized and tested series of 3-substituted benzisothiazole derivatives [3 -10] and more recently, we have discovered novel 2-aminobenzo[d]isothiazole-3-one derivatives displaying new, interesting biological properties. [11 -14] Although a lot of structural data have been reported in the literature concerning the chemistry of the benzofused isothiazoles, [1,2,15] detailed information about 1 H and 13 C NMR signals of the class of compounds is still lacking. In pursuing studies on this class of benzisothiazole derivatives, structural elucidation is a significant part of our work.…”

“…[1,2] The benzo [d]isothiazole ring can be a substituent of a bioactive scaffold or the pharmacophore of a bioactive molecule. For a number of years, we have designed, synthetized and tested series of 3-substituted benzisothiazole derivatives [3 -10] and more recently, we have discovered novel 2-aminobenzo[d]isothiazole-3-one derivatives displaying new, interesting biological properties.…”

“…In pursuing studies on this class of benzisothiazole derivatives, structural elucidation is a significant part of our work. So, we decided to perform the complete 1 H and 13 C NMR assignment of a novel 3-substituted derivative (1) and of the previously described 3-amino-5-methylbenzo [d]isothiazole (2), the parent compound of 5-methyl substituted benzo [d]isothiazoles extensively investigated by us (Table 1). [3,7 -9,16] Moreover, we report here the complete spectral assignment of the key intermediate (3) used for the synthesis of 2-aminobenzo[d]isothiazol-3-one derivatives [11 -14] and of its desulfurated isoster, the 2-aminoisoindolin-1-one analog (4) ( Table 2).…”

Synthesis of some naphthyl-substituted nitrogen heterocycles on the basis of (Z)-3-chloro-3-(2-naphthyl)propenal

“…The 13 C NMR spectrum of pyrazole II was reported in [4]; however, neither procedure for preparation of this compound nor its other spectral data were given (although the authors noted that this compound was previously unknown). The molecule of naphthylpyrazole II contains an N-nucleophilic center (NH); therefore, we examined its alkylation with 2-nitropentachloro-1,3-butadiene (III) which is known as a highly reactive electrophilic agent toward various amines [5]. The reaction involved replacement of both geminal chlorine atoms in the dichloronitrovinyl fragment of III and resulted in formation of a bis-pyrazole structure, 3,4,4-trichloro-1,1-bis[5-(2-naphthyl)pyrazol-1-yl]-2-nitro-1,3-butadiene (IV) (Scheme 1).…”