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Specific features of the reactions of quinazoline and its 4-hydroxy and 4-chloro substituted derivatives with C-nucleophiles |
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| Authors: | Yuri A. Azev Sergey V. Shorshnev |
| Affiliation: | a Ural Scientific Research Institute of the Technology of Medical Preparations, 620219 Ekaterinburg, Russian Federation b Department of Chemistry, Ural State Technical University, 620002 Ekaterinburg, Russian Federation c Chembridge Corporation, 119435 Moscow, Russian Federation |
| Abstract: | Reactions of quinazoline 1 with indole, pyrogallol and 1-phenyl-3-methylpyrazol-5-one in the presence of acid led to C-4 adducts 2, 3 and 5. Adduct 4 is formed by heating 1 with 1,3-dimethylbarbituric acid without acid catalysis. 1-Phenyl-3-methylpyrazol-5-one reacts with 1 without acid catalysis to form dipyrazolylmethane 6. 4-Chloroquinazoline 8 reacts with 1-phenyl-3-methylpyrazol-5-one to form 4-(1-phenyl-3-methyl-5-oxopyrazol-4-yl) quinazoline 9 and dipyrazolylmethane 6. Heating 8 with 2-methylindole leads to the formation of 4-(2-methylindol-3-yl) quinazoline 10 and tris(2-methylindol-3-yl)methane 11. |
| Keywords: | Quinazoline Nucleophiles Transformations |
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