Brønsted acid-catalyzed alkylation of tetrazoles with alcohols

Tetrazoles hold significant pharmaceutical importance, being a key component in various drugs with hypertensive, antimicrobial, antiviral, antiallergic, cytostatic and nootropic biological activities. Traditionally, tetrazoles have been alkylated using alkyl halides under basic conditions. However, alcohols are the most convenient alkylating reagents. While Lewis and Brønsted acid-catalyzed alkylations of tetrazoles using alcohols have been reported, their drawbacks include the necessity to use excess of strong Brønsted acid, narrow scope, long reaction time and poor functional group tolerance. Recently, we developed a methodology for the alkylation of 5-substituted tetrazoles with benzhydryl and benzylic alcohols in the presence of 5 mol% of a mild Brønsted acid catalyst HBF4 (aq). The developed protocol features low acid catalyst loading, short reaction times, generally high yields and high N2 selectivity. In addition, the developed methodology exhibits excellent functional group tolerance.

Name thesis:degree_name

Master of Science (MSc)

Discipline thesis:degree_discipline

Applied Bioscience

Grantor

University of Ontario Institute of Technology

Year dc:date.issued

2025

Author dc:creator

• Butt, Arsala

Advisor dc:contributor.advisor

• Bolshan, Yuri

Language dc:language.iso

en

Handle dc:identifier.uri

https://hdl.handle.net/10155/2001

OAI identifier oai:identifier

oai:ontariotechu.scholaris.ca:10155/2001