Regioselective Synthesis of 5-(Trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidines from β-Enamino Diketones

Abstract

The use of β-enamino diketones as an easy entry to the regioselective synthesis of [1,2,4]triazolo[1,5-a]pyrimidines is reported. These ketones reacted with 3-amino-1H-1,2,4-triazoles to furnish exclusively 6-substituted 5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidines in yields of up to 95%. The regioselectivity of the reactions performed was maintained regardless of the substituent in the starting ketone or aminoazole.

Key words

β-enamino diketones - 1,3-diones - triazolopyrimidines - aminotriazoles - fluorinated heterocycles

• References

• 1 Emelina EE, Petrov AA. Russ. J. Org. Chem. 2009; 45: 417
• 2 Okamura T, Kurogi Y, Hashimoto K, Nishikawa H, Nagao Y. Bioorg. Med. Chem. Lett. 2004; 14: 2443
• 3 Novinson T, Springer RH, O’Brien DE, Scholten MB, Miller JP, Robins RK. J. Med. Chem. 1982; 25: 420
• 4 Kleschick WA, Gerwick BC, Carson CM, Monte WT, Snider SW. J. Agric. Food Chem. 1992; 40: 1083
• 5 Nie J, Guo H.-C, Cahard D, Ma J.-A. Chem. Rev. 2011; 111: 455
• 6 Rulev AY, Romanov AR. RSC Adv. 2016; 6: 1984
• 7 Tsai SW. J. Mol. Catal. B: Enzym. 2016; 127: 98
• 8 Zhu W, Wang J, Wang S, Gu Z, Aceña JL, Izawa K, Liu H, Soloshonok VA. J. Fluorine Chem. 2014; 167: 37
• 9 Ruzziconi R, Buonerba F. J. Fluorine Chem. 2013; 152: 12
• 10 Kolosov MA, Kulyk OG, Starchenko OI, Orlov VD. Chem. Heterocycl. Compd. 2013; 49: 1166
• 11 Lipson VV, Desenko SM, Ignatenko IV, Shishkin OV, Shishkina SV. Russ. Chem. Bull. 2006; 55: 345
• 12 Lipson VV, Desenko SM, Orlov VD, Shishkin OV, Shirobokova MG, Chernenko VN, Zinov’eva LI. Chem. Heterocycl. Compd. 2000; 36: 1329
• 13 Druzhinin SV, Balenkova ES, Nenajdenko VG. Tetrahedron 2007; 63: 7753
• 14 Kuznetsova OA, Filyakova VI, Pashkevich KI, Ulomskii EN, Plekhanov PV, Rusinov GL, Kodess MI, Rusinov VL. Russ. Chem. Bull. 2003; 52: 1190
• 15 Boechat N, Pinheiro LC. S, Silva TS, Aguiar AC. C, Carvalho AS, Bastos MM, Costa CC. P, Pinheiro S, Pinto AC, Mendonça JS, Dutra KD. B, Valverde AL, Santos-Filho OA, Ceravolo IP, Krettli AU. Molecules 2012; 17: 8285
• 16 Liu YC, Qu RY, Chen Q, Yang JF, Cong-Wei N, Zhen X, Yang GF. J. Agric. Food Chem. 2016; 64: 4845
• 17 Krasovsky AL, Moiseev AM, Nenajdenko VG, Balenkova ES. Synthesis 2002; 901
• 18 Zanatta N, Amaral SS, dos Santos JM, Fernandes L. daS, Bonacorso HG, Martins MA. P. J. Heterocycl. Chem. 2011; 48: 1085
• 19 Frizzo CP, Scapin E, Marzari MR. B, München TS, Zanatta N, Bonacorso HG, Buriol L, Martins MA. P. Ultrason. Sonochem. 2014; 21: 958
• 20 Da Silva MJ. V, Poletto J, Jacomini AP, Pianoski KE, Gonçalves DS, Ribeiro GM, Melo SM. D. S, Back DF, Moura S, Rosa FA. J. Org. Chem. 2017; 82: 12590
• 21 Silva RG. M, Da Silva MJ. V, Jacomini AP, Moura S, Back DF, Basso EA, Rosa FA. RSC Adv. 2018; 8: 4773
• 22 Rosa FA, Machado P, Fiss GF, Vargas PS, Fernandes TS, Bonacorso HG, Zanatta N, Martins MA. P. Synthesis 2008; 3639
• 23 Souza TF, Silva MJ. V, Silva RG. M, Gonçalves DS, Simon PA, Jacomini AP, Basso EA, Moura S, Martins MA. P, Back DF, Rosa FA. Asian J. Org. Chem. 2017; 6: 627
• 24 Berber H, Soufyane M, Santillana-Hayat M, Mirand C. Tetrahedron Lett. 2002; 43: 9233
• 25 Touzot A, Soufyane M, Berber H, Toupet L, Mirand C. J. Fluorine Chem. 2004; 125: 1299
• 26 Mirand C, Soufyane M, van den Broek S, Khamliche L. Heterocycles 1999; 51: 2445
• 27 Rosa FA, Machado P, Rossatto M, Vargas PS, Bonacorso HG, Zanatta N, Martins MA. P. Synlett 2007; 3165
• 28 Chernyshev VM, Astakhov AV, Starikova ZA. Tetrahedron 2010; 66: 3301
• 29 Wang L.-H, Zhao J. Eur. J. Org. Chem. 2018; 4345
• 30 Souza L, Santos J, Mittersteiner M, Andrade V, Lobo M, Santos F, Bortoluzzi A, Bonacorso H, Martins M, Zanatta N. Synthesis 2018; 50: 3686
• 31 CCDC 1488187 (3e) and CCDC 1865842 (1b) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.