Diversified Aminohydantoins from Ureas and Thioureas Tethered to Amides

Intramolecular cyclization of thioureas or ureas tethered to amides afforded 2‐iminohydantoins and 2‐amino‐1H‐imidazol‐4(5H)‐ones in very high yields (87–100 %) regardless of the substituent (alkyls or aryls). This reaction proceeds through carbodiimides and iminium ions as intermediates. Among the...

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Veröffentlicht in:European journal of organic chemistry 2012-05, Vol.2012 (13), p.2542-2548
Hauptverfasser: Bepary, Sukumar, Youn, In Kwon, Lim, Hee-Jong, Lee, Ge Hyeong
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Sprache:eng
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Zusammenfassung:Intramolecular cyclization of thioureas or ureas tethered to amides afforded 2‐iminohydantoins and 2‐amino‐1H‐imidazol‐4(5H)‐ones in very high yields (87–100 %) regardless of the substituent (alkyls or aryls). This reaction proceeds through carbodiimides and iminium ions as intermediates. Among the reagents used to generate the carbodiimides, CBr4/Ph3P, CCl4/Ph3P, O,O′‐bis(2′‐pyridyl)thiocarbonate, and HgO were investigated. Intramolecular cyclization of thioureas or ureas tethered to amides afforded 2‐iminohydantoins and 2‐amino‐1H‐imidazol‐4(5H)‐ones in very high yields (87–100 %) regardless of the substituent (alkyls or aryls). This reaction proceeds through carbodiimides and iminium ions as intermediates.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201200025