Studies on the syntheses of heterocycles from 3-arylsydnone-4-carbohydroximic acid chlorides with N-arylmaleimides, [1,4]naphthoquinone and aromatic amines |
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Authors: | Mei-Hsiu Shih |
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Affiliation: | Department of Chemical Engineering, Southern Taiwan University of Technology, Tainan 710, Taiwan, ROC |
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Abstract: | 3-Arylsydnone-4-carbohydroximic acid chlorides (1) could react with N-arylmaleimides (3a–b) or 2-methyl-N-phenylmale-imide (3c) to give 3-(3-arylsydnon-4-yl)-5-aryl-3a,6a-dihydro-pyrrolo[3,4-d]isoxazole-4,6-diones (4a–h) or 6a-methyl-3-(3-arylsydnon-4-yl)-5-phenyl-3a,6a-dihydro-pyrrolo[3,4-d]isoxazole-4,6-diones (4i–l), respectively. However, 3-(arylsydnon-4-yl)-naphtho[2,3-d]isoxazole-4,9-diones (6a–d) were obtained in good yield by the reaction of carbohydroximic acid chlorides 1 with [1,4]naphthoquinone. Furthermore, 2-(3-arylsydnon-4-yl)benzoxazoles (9a–d) and 2-(3-arylsydnon-4-yl)benzothiazoles (9e–h) were obtained via the reaction of carbohydroximic acid chlorides 1 with ortho-substituted aromatic amines 7a and b. |
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Keywords: | nitrile oxides benzoxazoles benzothiazoles 3-arylsydnone-4-carbohydroximic acid chlorides 5-aryl-3-(3-arylsydnone-4-yl)-3a,6a-dihydro-pyrrolo[3,4-d]isoxazole-4,6-diones 3-(arylsydnon-4-yl)naphtho[2,3-d]isoxazole-4,9-diones |
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