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A convenient one-pot synthesis of 2-(trifluoromethyl)-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one derivatives and their further transformations |
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| Authors: | Shaodi Song Baifan Dai Guifang Jin Min Shao |
| Institution: | a Department of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, China b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China c Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, China |
| Abstract: | The trifluoromethyl containing heterocycles, 2-hydroxy-4-aryl-3-(thien-2-oyl)-2-(trifluoromethyl)-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one derivatives 4, were synthesized via a one-pot three-component reaction of aldehyde 1 with 1,3-cyclohexanedione 2 and 4,4,4-trifluoro-1-(thien-2-yl)butane-1,3-dione 3 in the presence of a catalytic amount of Et3N. The effect of bases and solvents on the reaction efficiency and yield was briefly investigated. Treatment of 4 with an excess amount of NH4OAc in ethanol afforded 2-trifluoromethyl-1H-quinolin-5-one derivatives 5. Refluxing of 4 with TsOH in CHCl3 gave the corresponding dehydrated products 8. |
| Keywords: | One-pot multi-component reaction Fluorinated heterocycles Trifluoromethyl-1 3-dione Dehydration |
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