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

摘要

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.