ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Thienoanneleted 6aλ4-Thia-1,6-diazapentalenes by Baseinduced Dimerisation of 5-Methyl-isothiazolium SaltsIsothiazolium salts 2 and 3 are easily available by reaction of (Z/E)-β-thiocyanatovinyl aldehydes with primary aliphatic and aromatic amines in acetic acid or with aromatic amine hydrochlorides, respectively. Preparative advantages of this reaction are demonstrated and discussed. Reaction of 3 with secondary amines results in an unexpected formation of 6aλ4-thia-1,6-diazapentalenes 5, a new typ of thiadiazapentalenes anellated with a heterocyclic ring system. The structure of 5 was evidenced by IR, UV, 1H-, 13C-n.m.r. spectral data and supported by elemental analysis. By means of 15N- and 13C-n.m.r. spectroscopy the synthesized thiadiazapentalenes were found to be stable towards protonation.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19923340105