A simple and efficient synthesis of novel N , N ′‐bis (1 H ‐pyrrol‐1‐yl)‐1‐[2‐(2‐aryl‐5‐methyl‐3‐oxo‐2,4‐dihydro‐3 H ‐1,2,4‐triazol‐4‐yl)ethyl]‐1 H ‐1,2,3‐triazole‐4,5‐dicarboxamides

• Published in: Journal of heterocyclic chemistry 2007-11, Vol.44 (6), p.1363-1371
• Main Authors: Latthe, Prashant R., Sunagar, Vinay A., Badami, Bharati V.
• Format: Article
• Language: English
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.5570440620

magnified image 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‐3 H ‐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]‐1 H ‐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.