Potassium Periodate Mediated Oxidative Cyclodesulfurization toward Benzofused Nitrogen Heterocycles

Chuthamat Duangkamol; Wong Phakhodee; Mookda Pattarawarapan

doi:10.1055/s-0039-1690855

Synthesis, Table of Contents

Synthesis 2020; 52(13): 1981-1990
DOI: 10.1055/s-0039-1690855

paper

Potassium Periodate Mediated Oxidative Cyclodesulfurization toward Benzofused Nitrogen Heterocycles

Authors

Chuthamat Duangkamol

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
Wong Phakhodee

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand

^bResearch Center on Chemistry for Development of Health Promoting Products from Northern Resources, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand Email: Mookdap55@gmail.com
Mookda Pattarawarapan∗

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand

^bResearch Center on Chemistry for Development of Health Promoting Products from Northern Resources, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand Email: Mookdap55@gmail.com

Abstract

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Abstract

A convenient oxidative cyclodesulfurization method toward the synthesis of benzofused nitrogen heterocycles using inexpensive and readily available potassium periodate as an oxidant was developed. Upon treating isothiocyanates with ortho-substituted anilines bearing N,N-, N,O-, and N,S-bis-nucleophiles, followed by an intramolecular cyclization of the in situ generated monothioureas, substituted 2-aminobenzazole series were rapidly accessible in good to excellent yields. The protocol can accommodate various substituents on both substrates while allowing more efficient, greener, and operational simpler process relative to other oxidative coupling reactions. Tetracyclic quinazolinone derivatives were also afforded in high yields in a single preparative step and chromatography-free.

Key words

cyclization - oxidation - 2-aminobenzimidazoles - 2-aminobenzoxazoles - 2-aminobenzothiazoles - quinazolinones - periodate

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References

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