DBN-Mediated Addition Reaction of α-(Trifluoromethyl)styrenes with Diazoles, Triazoles, Tetrazoles, and Primary, Secondary, and Secondary Cyclic Amines
Jingjing He, Chuan Liu, Yupian Deng, Qianding Zeng, Yi Zhang, Ying Liu, Pai Zheng and Song Cao*
*Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology (ECUST), Shanghai 200237, China,
Email: scao
ecust.edu.cn
J. He, C. Liu, Y. Deng, Q. Zeng, Y. Zhang, Y. Liu, P. Zheng, S. Cao, Org. Lett., 2022, 24, 2299-2304.
DOI: 10.1021/acs.orglett.2c00410
Abstract
A mild and efficient DBN-mediated addition of α-(trifluoromethyl)styrenes to diazoles, triazoles, tetrazoles, and primary, secondary, and secondary cyclic amines provides various β-trifluoromethyl nitrogen-containing heterocycles and β-trifluoromethyl amines.
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General procedure
To a glass tube charged with a stirring bar were added DBN (124.2 mg, 1.0 mmol, 1.0 equiv), 1-(formyl)-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene 1r (200.0 mg, 1.0 mmol), amine nucleophile (1.0 mmol, 1.0 equiv) and DMF (8 mL). The reaction vial was sealed with a rubber septum and then the reaction mixture was stirred at room temperature for 1 h (monitored by TLC and GC/MS). After the completion of reaction, the reaction mixture was quenched with saturated aqueous solution of NH4Cl (30 mL) and extracted with ethyl acetate (3 × 30 mL). The organic layer was separated and dried over Na2SO4, filtered and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel using n-hexane/ethyl acetate as eluent to afford the pure target compounds.
Key Words
ID: J54-Y2022
