Tandem Ritter and hydration reaction on γ-hydroxy-α,β-alkynoic esters: Synthesis of γ-N-acylamino-β-keto esters and ethyl 5-oxazoleacetates

ORGN 126

K. Srinivasa Rao, javediqbaldrf@hotmail.com1, D. Srinivasa Reddy1, Manojit Pal1, K. Mukkanti, javediqbaldrf@hotmail.com2, and Javed Iqbal1. (1) Discovery Research, Dr. Reddy’s Laboratories Ltd, Bollaram Road, Miyapur, Hyderabad, 500 049, India, (2) Chemistry Division, Institute of Science&Technology, Kukatpally, Hyderabad, 500 072, India, JNT University, Kukatpally, Hyderabad, 500 072, India, Hyderabad, 500 072, India
Ritter reaction on γ-hydroxy-α,β-alkynoic esters with alkyl nitriles followed by hydration in the presence of conc. H2SO4 produced γ-N-acylamino-β-keto esters, which are important building blocks in synthesis of natural products, heterocyles, and in peptidomimetics. The same reaction with aromatic nitriles resulted in ethyl-5-oxazoleacetate derivatives. Scope, limitations, and applications of this reaction will be presented in this poster