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Communication | Regular issue | Vol 14, No. 2, 1980, pp.149-157
Published online, 1st January, 1970
DOI: 10.3987/R-1980-02-0149
Heterocyclic Systems Containing Bridgehead Nitrogen Atom. Part XXXVII. Reaction of Marcapto-as-benzotriazines with Halogenoacetic Acid, α-Halogenoketones and Alkyl Halides

Saroj Bala, Madan Lal Sachdeva, Ram Nath Handa, and Hrushi Kesh Pujari*

*Department of Chemistry, Kurukshetra University, Kurukshetra-136119, India

Abstract

Mercapto-as-benzotriazines (IIa,b) obtained by the reaction of corresponding o-phenylenediamines (Ia,b) with thiosemicarbazide, on condensation with halogenoacetic acid, yields benzotriazine-3-thiolacetic acids (IIIa,b) which on treatment with acetic anhydride underwent cyclodehydration to furnish 9H-thiazolo[2,3-c]-as-benzotriazin-3(2H)-ones (IVa,b) and not 5H-thiazolo[3,2-b]-as-benzotriazin-3(2H)-ones (VIIIa,b) as revealed by NMR spectral data. Similar condensation of IIa,b with α-halogenoketones followed by the PPA cyclization of the intermediate ketones (Va,b) yields 9H-thiazolo[2,3-c]-as-benzotriazines (VIa,b). The reaction of IIa with 1,2-dibromoethane yields 9H-2,3-dihydro-6,7-dimethylthiazolo[2,3-c]-as-benzotriazine (VII). Thiazolo-benzotriazine (IV, VI and VII) is a novel and hitherto unknown heterocyclic system and is reported here for the first time.