Diversified Aminohydantoins from Ureas and Thioureas Tethered to Amides | Zendy

Bepary Sukumar | Zendy; Youn In Kwon | Zendy; Lim HeeJong | Zendy; Lee Ge Hyeong | Zendy

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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.

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