Studies with heteroaromatic amines. A new route to 2-azolylamino-2-thiazolin-4-ones

Authors: Khadijah M. Al-Zaydi Asma Al-Shamary,; Elnagdi, Mohamed H.

Source: Journal of Chemical Research, Volume 2006, Number 6, June 2006 , pp. 408-411(4)

Publisher: Science Reviews 2000 Ltd

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Abstract:

Heteroaromatic chloroacetamides 3a-c on treatment with potassium thiocyanate afforded the thiazolylamino-thiazolines 6a-c via intermediacy of 4a-c and 5a-c. Compounds 6a-c condensed with dimethylformamide dimethylacetal (DMFDMA) to yield the Z-enamines 7a-c. The enamines 7a and 7b could be converted into the enamines 8a-e and 9a,b on treatment with amines. However, reacting 10c with morpholine afforded 11b. Compounds 9a,b, as well as 9c, were also obtained on reacting 6a-c with triethyl orthoformate and piperidine in DMF. The structures of 6a and 11b were confirmed by X-ray crystal structure determination.

Keywords: 2-THIAZOLIN-4-ONES, ENAMINES, DMFDMA, DIMROTH REAR

Document Type: Research article

DOI: http://dx.doi.org/10.3184/030823406777946671

Publication date: 2006-06-01

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