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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| Published in | Synthesis (Stuttgart) Vol. 52; no. 13; pp. 1981 - 1990 |
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| Language | English |
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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 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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| AbstractList | 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. |
| Author | Pattarawarapan, Mookda Duangkamol, Chuthamat Phakhodee, Wong |
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| Keywords | 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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| Title | Potassium Periodate Mediated Oxidative Cyclodesulfurization toward Benzofused Nitrogen Heterocycles |
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