Reactions of hydrazidoyl halides: synthesis of imidazo[2,1-b]thiazole, thiazolo[2,3-c]-as-triazole and heterocyclic enaminonitriles
TL;DR: Arylazo derivatives of imidazo[2,1-b]thiazoles could be obtained via reaction of hydrazidoyl halides with 2-aminothiazole as mentioned in this paper.
Abstract: Arylazo derivatives of imidazo[2,1-b]thiazoles could be obtained via reaction of hydrazidoyl halides with 2-aminothiazole. Thiazolo[2,3-c]-as-triazole and heterocyclic enaminonitriles were obtained in good yields from hydrazidoyl halides and triethylamine and from malonitrile, respectively. Pyrazolo[3,4-d]pyrimidines and pyrazolo[3,4-d]pyridazines were obtained via reaction of heterocyclic enaminonitriles with formic acid and hydrazine hydrate, respectively. The structures of the products were assigned and confirmed on the basis of their elemental analyses and spectral data.
Cites background from "Reactions of hydrazidoyl halides: s..."
...In another report , it was indicated that reaction of other 2-amino-4-methylthiazole derivatives 34 with the 2oxohydrazonoyl halides 1A, B led to the formation of the respective 5-arylazoimidazo[2,1-b]thiazoles 35 (Scheme 12)....
... to yield, however, the other isomeric products 38 (Scheme 13) ....
...Similar reaction of 2-aminobenzothiazole 210 with ethyl N(arylhydrazono)chloroacetate 1B afforded 212 via cyclization of the initially formed respective amidrazone (Scheme 72) ....
...Imidazo[2,1-b]benzothiazoles Reactions of 2-aminobenzothiazole 210 with N-aryl 2oxopropanehydrazonoyl chloride 1A and N-aryl 2-oxo-2phenylethanehydrazonoyl bromides 1E were reported to give the respective 3-arylazoimidazo[1,2-a]benzothiazoles 211 (Scheme 72) ....
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