Parallel synthesis of 1,2,4-triazole derivatives using microwave and continuous-flow techniques
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An efficient and convenient solution-phase synthesis of a 1H-1,2,4-triazole library with potential agrochemical activity is reported employing microwave-assisted organic synthesis (MAOS) and continuous-flow microfluidic synthetic methods starting from commercially available 3,5-dibromo-1H-1,2,4-triazole (1). MAOS was used for the synthesis of 5-amino-3-bromo-1,2,4-triazole analogs 3 and for their 3-aryl derivatives 4 via Suzuki–Miyaura coupling with polymer-supported catalyst. A microfluidic hydrogenation reactor integrated into an automated parallel synthesis platform was built and utilized for the reductive dehalogenation reactions providing 5-aminotriazoles (5).
KeywordsMicrowave-assisted organic synthesis Continuous-flow hydrogenation 1H-1,2,4-triazole
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- 1.New Report Global Biopesticides Market (2010–2015) Shifting Trends in Agrochemical Industry Published By MarketsandMarkets, http://www.marketsandmarkets.com
- 2.Shaber SH, Flynn KE, Fujimoto TT (1993) (Heterocyclylalkyl) ethyl-1,2,4-triazoles. EP0529973Google Scholar
- 5.Prasad AR, Rao AN, Ramalingan T, Sattur PB (1988) Synthesis and biological activity 4-amino-3-aryloxyalkyl-5-mercapto-1,2,4-triazoles. Indian Drugs 25(7): 301–304Google Scholar
- 7.Maxwell JR, Wasdahl DA, Weltson DC, Stenberg VI (1984) Synthesis of 5-aryl-2H-tetrazoles, 5-aryl-2H-tetrazole-2-acetic acids, and [(4-phenyl-5-aryl-4H-1,2,4-triazol-3-yl)thio]acetic acids as possible superoxide scavengers and antiinflammatory agents. J Med Chem 27: 1565–1570. doi: 10.1021/jm00378a007 PubMedCrossRefGoogle Scholar
- 9.Libnow S, Wille S, Christiansen A, Hein M, Reinke H, Köckerling M, Miethchen R (2006) Synthesis and reactivity of halogenated 1,2,4-triazole nucleoside analogues with high potential for chemical modifications. Synthesis 496–508. doi: 10.1055/s-2006-926281
- 10.Zumbrunn A (1998) The first versatile synthesis of 1-alkyl-3-fluoro-1H-[1,2,4]triazoles. Synthesis 1357–1361. doi: 10.1055/s-1998-6080
- 11.Glunz PW, Wurtz N, Cheng X (2006) Heterocyclic compounds as inhibitors of factor VIIA. WO2006062972A2Google Scholar