A simple and efficient synthesis of novel N,N′‐bis (1H‐pyrrol‐1‐yl)‐1‐[2‐(2‐aryl‐5‐methyl‐3‐oxo‐2,4‐dihydro‐3H‐1,2,4‐triazol‐4‐yl)ethyl]‐1H‐1,2,3‐triazole‐4,5‐dicarboxamides
Post Graduate Department of Studies in Chemistry, Karnatak University, Dharwad ‐ 580 003, INDIA
Abstract:
One‐pot reaction of 3‐aryl‐5‐methyl‐1,3,4‐oxadiazolin‐2‐ones 1a‐g with ethanolamine yielded the 4‐(2‐hydroxyethyl)‐2‐aryl‐5‐methyl‐2,4‐dihydro‐3H‐1,2,4‐triazolin‐3‐ones 2a‐g which were converted to the azido compounds 6a‐g . These azides on 1,3‐dipolar cycloaddition with DMAD afforded the dimethyl‐1‐[2‐(2‐aryl‐5‐methyl‐3‐oxo‐1,2,4‐triazol‐4‐yl)ethyl]‐1H‐1,2,3‐triazol‐4,5‐dicarboxylates 7a‐g which on conversion to bishydrazides 8a‐g and further cyclisation with 2,5‐hexanedione afforded the title compounds 9a‐g . This new short route for the so far unkown bis‐(triazolinone‐triazole)ethanes involves mild and convergent 1,3‐dipolar cycloaddition reaction yielding overall good yields of the products.
