New synthesis of 2-trifluoromethyl-2,3-dihydro-1H-quinolin-4-ones |
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| Authors: | Yuefa Gong |
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| Affiliation: | a Department of Chemistry, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, PR China
b National Institute of Advanced Industrial Science and Technology (AIST), Anagohara, Shimoshidami, Moriya-ku, 2266-98 Nagoya, Japan |
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| Abstract: | N-(1-Ethoxy-2,2,2-trifluoroethyl)anilines 2a-2f, prepared from trifluoroacetaldehyde ethyl hemiacetal and aniline, readily reacted with diethyl malonate in the presence of sodium hydride, giving substituted products 5a-5f in high yields. Compounds 5a-5f subjected to hydrolysis and decarboxylation under specified conditions yielded the 4,4,4-trifluorobutyric acids 6a-6e or 7. Direct ring-closure of 6a-6e with polyphosphoric acid gave 2-trifluoromethyl-2,3-dihydro-1H-quinolin-4-ones 9a-9e. |
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| Keywords: | Quinolinone Trifluoroacetaldehyde Ring-closure 3-Anilino-4,4,4-trifluorobutyric acid |
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