Potassium Periodate Mediated Oxidative Cyclodesulfurization toward Benzofused Nitrogen Heterocycles

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 withortho-substituted anilines bearingN,N-,N,O-, andN,S-bis-nucleophiles,...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 52; no. 13; pp. 1981 - 1990
Main Authors Duangkamol, Chuthamat, Phakhodee, Wong, Pattarawarapan, Mookda
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.07.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DESIGN
ACID
ONE-POT SYNTHESIS
2-aminobenzothiazoles
oxidation
cyclization
SUBSTITUTED 2-AMINOBENZIMIDAZOLES
2-aminobenzimidazoles
DOMINO 3-COMPONENT APPROACH
AMINATION
periodate
2-aminobenzoxazoles
BENZOXAZOLES
DESULFURIZATION
quinazolinones
CONCISE SYNTHESIS
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Summary: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 withortho-substituted anilines bearingN,N-,N,O-, andN,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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0039-1690855