Synthetic exploitation of the ring-opening of 3,4-dinitrothiophene. Part 7. Access to disubstituted 1,2,5-oxadiazole-2-oxides and 2-phenyl-2H-1,2,3-triazole-1-oxides

✍ Scribed by Vania Armani; Carlo Dell'Erba; Novi Marino; Giovanni Petrillo; Cinzia Tavani

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 591 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)01086-1

✦ Synopsis

1.4-Dlalkyl-and 1,4-diar~I-~,3-bls(hydr(~~~lmlno)butancs 7, 1rom reductton ol the corresponding 1,4-dlsubsututed 23.dmltrw I ,3-butadlenes 2, are transformed M Ith satlsl'actor> ytelds Into 3,4disubstituted 1,?,5-oxadt~~~le-2-o-rlde 5 and 4,S-disubstttuted ?-phen~l-2H-1,2.3-triazole-l-ou~des 6. Dtmtrobutadtenes 2 are obtamed from the reaction of 3,4-dmttrothtophene rwth diethylamme and subsequent treatment of'the ensumg bls(diethylamlno)butadlene 1 wth Gngnard reagents; thus the 01 erall transformation represents a novel approach IO I,?,~-oudiuole and 1,2,3-trwolc qstems 1 M a nng-