Synthesis and Characterization of 4′-Bromomethyl-2-(N-trityl-1H-tetrazol-5-yl) Biphenyl

Abstract

Biphenyl tetrazole ring is an important component of the Sartan family of novel drugs. 4′-Bromomethyl-2-(N-trityl-1H-tetrazol-5-yl)biphenyl was synthesized in this article from 4′-methyl-2-cyano-biphenyl through three steps. 4′-Methyl-2-cyano-biphenyl was reacted with azide ions with the help of ammonium chloride as catalyst in an autoclave with high conversion to afford the tetrazole compounds in 70.6% yield. After being protected by the trityl group with 92.6% yield, 4′-methyl-2-(N-trityl-1H-tetrazol-5-yl) biphenyl was brominated with N-bromosuccinimide (NBS) in cyclohexane with 2,2′-azo-isobutyronitrile (AIBN) acting as an initiator to provide the title compound in 83.8% yield.

Keywords:

• Angiotensin II
• free radical bromination
• synthesis
• tetrazole ring
• trityl protection

ACKNOWLEDGMENT

We are grateful to Professors Z. H. He and H. J. Lu from Zhengzhou University for their help.