Ionic Liquid–Mediated One-Pot Synthesis of 5-(Trifluoromethyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine Derivatives

Abstract

A facile one-pot synthesis of 5-(trifluoromethyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives is described via a three-component reaction of aldehydes with 5-aminotetrazole and ethyl 4,4,4-trifluoro-3-oxobutanoate or 4,4,4-trifluoro-1-phenylbutane-1,3-dione in ionic liquid. This method has the advantages of short synthetic route, operational simplicities, good yields, ecofriendliness, and recyclability of the solvent.

GRAPHICAL ABSTRACT

Keywords:

• Cyclization
• ionic liquid
• tetrazolo[1,5-a]pyrimidine
• trifluoromethylated

ACKNOWLEDGMENTS

We are grateful for financial support by the Natural Science Foundation of China (Nos. 20672090 and 200810102050), the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (09KJA430003), the Natural Science Foundation of Xuzhou City (XM09B016), the Graduate Foundation of Xuzhou Normal University (09YLB030), and the Qing Lan Project (08QLT001).

Notes

^a [byp⁺][],1-butylpyridinium tetrafluoroborate, [bmim⁺][], 3-butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate.

^b Isolated yield.

^a [bmim⁺][] was used as solvent.

^b Isolated yield.

^a Isolated yield.

^a Isolated yield.