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Molecular‐Iodine‐Mediated, Efficient One‐Pot Synthesis of 2‐Iminohydantoins and 2‐Amino‐1H‐imidazol‐4(5H)‐ones by Cyclodeselenization of Selenourea‐Tethered Amides/Peptides
Author(s) -
Prabhu Girish,
Santhosh L.,
Nagendra G.,
Panduranga Veladi,
Sureshbabu Vommina V.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601858
Subject(s) - iodine , tripeptide , chemistry , intramolecular force , combinatorial chemistry , amino acid , substrate (aquarium) , organic chemistry , biochemistry , oceanography , geology
An efficient one‐pot synthesis of 2‐iminohydantoins and 2‐amino‐1H‐imidazol‐4(5H)‐ones via iodine mediated intramolecular cyclodeselenization of intermediate selenourea tethered amides/peptides is described. The method employs selenophilic ability of environmentally benign iodine to effect the deselenization at room temperature, thereby avoids harsh conditions that are generally employed in the synthesis of iminohydantoins. Significantly 2‐(N‐alkylamino)‐1H‐imidazol‐4(5H)‐ones and 2‐iminohydantoin conjugates of di‐ and tripeptides could be synthesized. Other advantages of the method include mild condition, short duration, wide substrate scope, simple workup and purification of the products.