Acylation and Cyclodehydration of Benzofuran-, Benzothiophene-, and Indolyl-3-acetic Acid Arylamides. Synthesis of Novel Benzofuro[2,3-c]-, Benzothieno[2,3-c], and Indolo[2,3-c]pyrilium and Pyridine Derivatives |
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Authors: | S. V. Tolkunov V. S. Tolkunov V. I. Dulenko |
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Affiliation: | (1) L. M. Litvinenko Institute of Physical Organic and Carbon Chemistry, National Academy of Sciences of Ukraine, Donetsk, 83114 |
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Abstract: | The acylation of benzo[b]furan-, benzo[b]thiophene, and indolyl-3-acetic acid arylamides using acetic anhydride in the presence of 70% perchloric acid occurs at the -position of the heterocycle to give 2-acetylbenzo[b]furan-, 2-acetylbenzo[b]thiophene, and 2-acetylindolyl-3-acetic acid arylamides. Depending on the amount of perchloric used in the reaction they undergo cyclodehydration to 3-arylamino-1-methylhetero[2,3-c]pyrilium salts and to N-aryl-1-methyl-3(2H)hetero[2,3-c]pyridones. |
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Keywords: | 2-acetylbenzo[b]thiophene-3-acetic acid arylamides 2-acetylbenzo[b]furan-3-acetic acid arylamides 2-acetylindolyl-3-acetic acid arylamides 3-arylamino-1-methylhetero[2,3-c]pyrilium N-aryl-1-methyl-3(2H)hetero[2,3-c]pyridones cyclodehydration |
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