A convenient one-pot synthesis of 2-(trifluoromethyl)-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one derivatives and their further transformations

作者：Song Shaodi; Song Liping^*; Dai Baifan; Yi Hai; Jin Guifang; Zhu Shizheng; Shao Min

来源：Tetrahedron, 2008, 64(24): 5728-5735.

DOI：10.1016/j.tet.2008.04.020

• one-pot multi-component reaction
• fluorinated heterocycles
• trifluoromethyl-1,3-dione
• dehydration

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 Et(3)N. The effect of bases and solvents on the reaction efficiency and yield was briefly investigated. Treatment of 4 with an excess amount of NH(4)OAc in ethanol afforded 2-trifluoromethyl-1H-quinolin-5-one derivatives 5. Refluxing of 4 with TsOH in CHCl(3) gave the corresponding dehydrated products 8.

• 出版日期2008-6-9
• 单位中国科学院; 上海大学