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 |
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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. |
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ISSN: | 1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.201200025 |