Tandem Ring Opening and Oximation of Ethyl 3‐Aroyl‐1‐cyano‐4‐hydroxy‐2,4,6‐triarylcyclohexanecarboxylate by Hydroxylamine

Abstract

The reaction of hydroxylamine hydrochloride with ethyl 3‐aroyl‐1‐cyano‐4‐hydroxy‐2,4,6‐triarylcyclohexanecarboxylate has led to the formation of ethyl 2‐[amino(hydroxyimino)methyl]‐3‐aryl‐5‐(hydroxyimino)‐5‐arylpentanoate via a tandem ring opening and oximation process. The structures of the products are confirmed by NMR and X‐ray techniques, and the conformational features of the product arrived at are compared with a molecular dynamics simulation study.

Keywords:

• 3‐aroyl‐1‐cyano‐4‐hydroxy‐2,4,6‐triarylcyclohexanecarboxylate
• NMR analysis
• PM3 calculation
• tandem reaction
• X‐ray structure

Acknowledgments

The authors thank Department of Science and Technology (DST), New Delhi, for the NMR facility under the Intensified Research in High Priority Area (IRHPA) program and DST (Funds for Improvement of Science and Technology (FIST)), New Delhi, for the single‐crystal X‐ray diffractometer facility. Financial support from Council of Scientific and Industrial Research (CSIR), New Delhi, for S. Saravanan is gratefully acknowledged.