A Simple and Efficient Synthesis of 3,4,5-Trisubstituted/N-Fused 1,2,4-Triazoles via Ceric Ammonium Nitrate Catalyzed Oxidative Cyclization of Amidrazones with Aldehydes Using Polyethylene Glycol as a Recyclable Reaction Medium

Abstract

An environmentally benign protocol is described for the synthesis of 3,4,5-trisubstituted 1,2,4-triazoles and N-fused 1,2,4-triazoles via ceric ammonium nitrate catalyzed oxidative cyclization of amidrazones and aldehydes using polyethylene glycol as recyclable reaction medium. This protocol is effective toward various substrates having different functionalities. The easy recyclability of the reaction medium makes the process economic and potentially viable for commercial applications.

Key words

polyethylene glycol - ceric ammonium nitrate - 1,2,4-triazoles - [1,2,4]triazolo[4,3-a]pyridines - [1,2,4]triazolo[4,3-a]pyrazines

• References

• 1a Mulakayla N, Reddy CH U, Iqbal J, Pal M. Tetrahedron 2010; 66: 4919
• 1b Bo Y, Lin C, Ruiying F, Zhiping G. Eur. J. Pharmacol. 1999; 380: 145
• 1c Yang B, Fang R. Acta Pharm. Sin. 1996; 17: 361
• 1d Li C.-S, An C.-Y, Li X.-M, Gao S.-S, Cui C.-M, Sun H.-F, Wang B.-G. J. Nat. Prod. 2011; 74: 1331
• 1e Zhou X, Xu T, Wen K, Yang X.-W, Xu S.-H, Liu Y. Biosci. Biotechnol. Biochem. 2010; 74: 1089
• 2 Collin X, Sauleau A, Coulon J. Bioorg. Med. Chem. Lett. 2003; 13: 2601
• 3 Papakonstantinou-Garoufalias S, Pouli N, Marakos P, Chytyroglou-Ladas A. Farmaco 2002; 57: 973
• 4 De Clercq E. J. Clin. Virol. 2004; 30: 115
• 5 Navidpour L, Shadnia H, Shafaroodi H, Amini M, Dehpour AR, Shafiee A. Bioorg. Med. Chem. 2007; 15: 1976
• 6 Naito Y, Akahoshi F, Takeda S, Okada T, Kajii M, Nishimura H, Sugiura M, Fukaya C, Kagitani Y. J. Med. Chem. 1996; 39: 3019
• 7 Saha AK, Liu L, Simoneaux R, Decorte B, Meyer C, Skrzat S, Breslin HJ, Kukla MJ, End DW. Bioorg. Med. Chem. Lett. 2005; 15: 5407
• 8 Hester JB. Jr, Rudzik AD, Kamdar BV. J. Med. Chem. 1971; 14: 1078
• 9 Hitotsuyanagi Y, Motegi S, Fukaya H, Takeya K. J. Org. Chem. 2002; 67: 3266
• 10a Dash C, Shaikh MM, Ghosh P. J. Chem. Sci. 2011; 123: 97
• 10b Sudheer Quraishi MA. Corros. Sci. 2013; 70: 161
• 10c Meyer D, Strassner T. J. Org. Chem. 2011; 76: 305
• 10d Klingele MH, Brooker S. Coord. Chem. Rev. 2003; 241: 119
• 10e Haasnoot JG. Coord. Chem. Rev. 2000; 131: 200
• 11a Holm SC, Straub BF. Org. Prep. Proced. Int. 2011; 43: 319
• 11b Moulin A, Bibian M, Blayo A.-L, Habnouni SE, Martinez J, Fehrentz J.-A. Chem. Rev. 2010; 110: 1809
• 11c Garratt PJ In Comprehensive Heterocyclic Chemistry II . Vol. 4. Storr RC. Elsevier; Oxford: 1996: 127-163
• 11d Al-Masoudi A, Al-Soud YA, Al-Salihi NJ, Al-Masoudi NA. Chem. Heterocycl. Compd. 2006; 42: 1377
• 12a Meanwell NA, Romine JL, Rosenfeld MJ, Martin SW, Trehan AK, Wright JJ. K, Malley MF, Gougoutas JZ, Brassard CL, Buchanan JO, Federic ME, Fleming JS, Gamberdella M, Hartl KS, Zavoico GB, Seiler SM. J. Med. Chem. 1993; 36: 3884
• 12b Reichelt A, Falsey JR, Rzasa RM, Thiel OR, Achmatowicz MM, Larsen RD, Zhang D. Org. Lett. 2010; 12: 792
• 12c Hajos Gy, Messmer A. J. Heterocycl. Chem. 1978; 15: 463
• 12d Jones G In Advances in Heterocyclic Chemistry . Katritzky AR. Elsevier Science; San Diego: 2002
• 13a Molander GA. Chem. Rev. 1992; 92: 29
• 13b Hwu JR, King KY. Curr. Sci. 2001; 81: 1043
• 13c Nair V, Mathew J, Prabhakaran J. Chem. Soc. Rev. 1997; 26: 127
• 13d Hwu JR, Chen CN, Shaio S.-S. J. Org. Chem. 1995; 60: 826
• 14a Chandrasekhar S, Narasimhulu Ch, Sultana SS, Reddy NR. Org. Lett. 2002; 4: 4399
• 14b Chandrasekhar S, Narasimhulu Ch, Saritha B, Sultana SS. Tetrahedron Lett. 2004; 45: 5865
• 14c Mao J, Guo J, Fang F, Ji S.-J. Tetrahedron 2008; 64: 3905
• 15 Mangarao N, Mahaboob Basha G, Ramu T, Srinuvasarao R, Prasanthi S, Siddaiah V. Tetrahedron Lett. 2014; 55: 177
• 16 Siddaiah V, Mahaboob Basha G, Ramu T, Mangarao N, Sudhakar D, Santosh KY, Christopher V. Tetrahedron Lett. 2014; 55: 2691
• 17 Siddaiah V, Mahaboob Basha G, Padma Rao G, Viplava Prasad U, Suryachendra Rao R. Synth. Commun. 2012; 42: 627
• 18 Mazaahir K, Anwar J, Divya B. J. Chem. Sci. 2010; 122: 607
• 19 Thiel OR, Achmatowicz MM, Reichelt A, Larsen RD. Angew. Chem. Int. Ed. 2010; 49: 8395