Novel Synthesis and Stereochemical Structure of 2H-2,6-Methano-1,3-Benzoxazocine-5-Carbohydrazides

Abstract

A novel synthetic approach for 5,6-dihydro-2,4-disubstituted-2 H-2,6-methano-1,3-benzoxazocine-5-carbohydrazides 4a–j was achieved through the reaction of 1-aryl-3-(2-hydroxyphenyl)prop-2-en-1-ones 1a–c with cyanoacetohydrazones 2a,b in the presence of sufficient amount of secondary amines 3a,b. Single crystal X-ray diffraction study of 4c supports the established structure and reveals that the relative configuration is 2 R,5 S,6 R.