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Diversified Aminohydantoins from Ureas and Thioureas Tethered to Amides
Author(s) -
Bepary Sukumar,
Youn In Kwon,
Lim HeeJong,
Lee Ge Hyeong
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200025
Subject(s) - chemistry , iminium , substituent , intramolecular force , reagent , medicinal chemistry , organic chemistry , thiourea , ion
Intramolecular cyclization of thioureas or ureas tethered to amides afforded 2‐iminohydantoins and 2‐amino‐1 H ‐imidazol‐4(5 H )‐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, CBr 4 /Ph 3 P, CCl 4 /Ph 3 P, O , O′ ‐bis(2′‐pyridyl)thiocarbonate, and HgO were investigated.