Journal
SYNTHESIS-STUTTGART
Volume 52, Issue 13, Pages 1981-1990Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690855
Keywords
cyclization; oxidation; 2-aminobenzimidazoles; 2-aminobenzoxazoles; 2-aminobenzothiazoles; quinazolinones; periodate
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Funding
- Thailand Research Fund through the Royal Golden Jubilee Ph.D. Programme [PHD/0086/2557]
- Chiang Mai University
- Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education Commission, Ministry of Education, Thailand
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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.
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