Complementary regioselectivity in the synthesis of iminohydantoins: remarkable effect of amide substitution on the cyclization†‡
María García-Valverde,Stefano Marcaccini,Alfonso González-Ortega,Francisco Javier Rodríguez,Josefa Rojo,Tomás Torroba
Organic & Biomolecular Chemistry Pub Date : 12/05/2012 00:00:00 , DOI:10.1039/C2OB27098F
Abstract

Complementary regioselective synthesis of iminohydantoins from isocyanoacetamides controlled by the substituent on the amide group has been described. 4-Iminohydantoins were the major products when the starting materials were N-alkyl isocyanoamides, whereas 2-iminohydantoins were the major products with N-aryl isocyanoamides.

Graphical abstract: Complementary regioselectivity in the synthesis of iminohydantoins: remarkable effect of amide substitution on the cyclization