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Synthesis 2020; 52(13): 1981-1990
DOI: 10.1055/s-0039-1690855
DOI: 10.1055/s-0039-1690855
paper
Potassium Periodate Mediated Oxidative Cyclodesulfurization toward Benzofused Nitrogen Heterocycles
This work was supported by The Thailand Research Fund through the Royal Golden Jubilee Ph.D. Programme (Grant No. PHD/0086/2557) to C.D. This research work was also partially supported by Chiang Mai University and the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education Commission, Ministry of Education, Thailand.Further Information
Publication History
Received: 02 January 2020
Accepted after revision: 26 February 2020
Publication Date:
16 March 2020 (online)
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 - periodateSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690855.
- Supporting Information
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