Reactivity of 3-formyl- and 3-cyanothiochromones toward some N- and C-nucleophiles. Novel synthesis of 3-substituted 2-aminothiochromones |
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Authors: | Vyacheslav Ya. Sosnovskikh Dmitri V. Sevenard Viktor O. Iaroshenko |
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Affiliation: | a Department of Chemistry, Ural State University, 620083 Ekaterinburg, Russian Federation b Hansa Fine Chemicals GmbH, BITZ, Fahrenheitstrasse 1, 28359 Bremen, Germany c Institut für Chemie, Universität Rostock, Albert-Einstein-Strasse 3a, 18059 Rostock, Germany |
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Abstract: | The reactions of 3-formylthiochromone with o-phenylenediamines, o-aminobenzenethiol, and indoles proceeded at the aldehyde group to give 3-(benzimidazol-2-yl)thiochromone, 3-(benzothiazol-2-yl)thiochromone, and 3-di(indol-3-yl)methylthiochromones, respectively. 3-Formyl- and 3-cyanothiochromones react with primary aromatic amines and phenylhydrazine to give the corresponding anils and phenylhydrazones of 3-formyl- and 2-amino-3-formylthiochromones. The reaction of 3-cyanochromones with o-phenylenediamines gave 2-amino-3-[(2-aminophenyl)iminomethyl]-4H-chromen-4-ones. |
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Keywords: | 3-Formyl- and 3-cyanothiochromones Anils and phenylhydrazones of 3-formyl- and 2-amino-3-formylthiochromones 3-(Benzimidazol-2-yl)- and 3-(benzothiazol-2-yl)thiochromones 3-Di(indol-3-yl)methylthiochromones Nucleophilic addition Regioselectivity |
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