A study of the reaction of 2-thiazolin-4-ones with some electrophiles under microwave irradiation versus conventional condition |
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Authors: | Khadijah M Al-Zaydi |
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Institution: | Chemistry Department, Girls’ College of Education, King Abdul-Aziz University, Jeddah, P.O. Box 50918, Jeddah 21533, Saudi Arabia |
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Abstract: | Coupling of 5-dimethylaminomethylene-3-methyl-2-(pyridine-2-ylimino)-thiazolidin-4-one (3) with diazotized methyl anthranilate afforded the 3-methyl-5-(2-methoxycarbonylphenylhydrazono)-2-pyridine-2-ylimino)thiazolidin-4-one (5). Reaction of 2-(arylamino)thiazol-4-ones 1a,b with arylidenemalononitriles under microwave irradiation gave 2-substituted amino-5-arylidenethiazolin-4-ones 9a–f. Alternatively, compound 9 could also be obtained by reacting compound 1 with aromatic aldehydes. Treatment of compound 9 with acetic acid yielded the corresponding thiazolin-2,4-diones 10. However, the reaction of 1 with cyanoacetic acid yielded the corresponding 4-cyanoacetyl derivative 12, in good yield. The 1H, 13C NMR spectra of some representative products and X-ray crystal structure determination are discussed. |
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Keywords: | 2-Thiazolin-4-one derivatives Microwave irradiation Enamines X-ray crystal structure determination |
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