Solvent- and Metal-Controlled Regiodivergent Synthesis of Tri­fluoromethylated Pyrazol-3-yl- and Pyrazol-5-ylphosphonates

Abstract

Convenient approaches to the selective syntheses of trifluoro­methylated pyrazol-3-yl- and pyrazol-5-ylphosphonates have been developed based on solvent- and metal-controlled reaction of diethyl (4,4,4-trifluoro-3-oxobut-1-yn-1-yl)phosphonate and monosubstituted hydrazines.

Key words

pyrazoles - phosphonates - cyclization - conjugated ynones - organofluorine compounds

Publication History

Received: 15 September 2021

Accepted after revision: 08 November 2021

Accepted Manuscript online:
08 November 2021

Article published online:
04 January 2022

• References

• 1a Fustero S, Sánchez-Roselló M, Barrio P, Simón-Fuentes A. Chem. Rev. 2011; 111: 6984
• 1b Ji Ram V, Sethi A, Nath M, Pratap R. Five-Membered Heterocycles . In The Chemistry of Heterocycles, Chap. 5 . Elsevier; Amsterdam: 2019: 149-478
• 2a Ojwach SO, Darkwa J. Inorg. Chim. Acta 2010; 363: 1947
• 2b Withbroe GJ, Singer RA, Sieser JE. Org. Process Res. Dev. 2008; 12: 480
• 2c Mukherjee A, Sarkar A. ARKIVOC 2003; (ix): 87
• 3a El Boutaybi M, Taleb A, Touzani R, Bahari Z. Mater. Today: Proc. 2020; 31: S96
• 3b Halcrow MA. Dalton Trans. 2009; 2059
• 3c Pérez J, Riera L. Eur. J. Inorg. Chem. 2009; 4913
• 3d Trofimenko S. Prog. Inorg. Chem. 1986; 34: 115-210
• 4a Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
• 4b Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
• 4c Hagmann WK. J. Med. Chem. 2008; 51: 4359
• 4d Berger R, Resnati G, Metrangolo P, Weber E, Hulliger J. Chem. Soc. Rev. 2011; 40: 3496
• 5a Zhou Y, Wang J, Gu Z, Wang S, Zhu W, Aceña JL, Soloshonok VA, Izawa K, Liu H. Chem. Rev. 2016; 116: 422
• 5b Mykhailiuk PK. Chem. Rev. 2021; 121: 1670
• 5c Meyer F. Chem. Commun. 2016; 52: 3077
• 5d Nenajdenko VG. Fluorine in Heterocyclic Chemistry . Springer; Berlin: 2014
• 5e Petrov VA. Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications. Wiley; Hoboken: 2009
• 5f Gakh AA, Kirk KL. Fluorinated Heterocycles . ACS Symposium Series, Oxford University Press/American Chemical Society; Washington DC: 2009
• 6a Iaroshenko V. Organophosphorus Chemistry: From Molecules to Applications. Wiley; Hoboken: 2019
• 6b Dutartre M, Bayardon J, Jugé S. Chem. Soc. Rev. 2016; 45: 5771
• 6c Timperley C. Best Synthetic Methods: Organophosphorus(V) Chemistry. Academic Press; London: 2015
• 6d Queffélec C, Petit M, Janvier P, Knight DA, Bujoli B. Chem. Rev. 2012; 112: 3777
• 6e Pradere U, Garnier-Amblard EC, Coats SJ, Amblard F, Schinazi RF. Chem. Rev. 2014; 114: 9154
• 6f George A, Veis A. Chem. Rev. 2008; 108: 4670
• 6g Quin LD. A Guide to Organophosphorus Chemistry . Wiley-Interscience; New York: 2000
• 7 Goulioukina NS, Makukhin NN, Beletskaya IP. Russ. Chem. Rev. 2016; 85: 667
• 8a Duda B, Tverdomed SN, Röschenthaler G.-V. RSC Adv. 2012; 2: 9135
• 8b Duda B, Tverdomed SN, Bassil BS, Röschenthaler G.-V. Tetrahedron 2014; 70: 8084
• 8c Duda B, Tverdomed SN, Ionin BI, Röschenthaler G.-V. Eur. J. Org. Chem. 2012; 3684
• 8d Mitrofanov AY, Bychkova VA, Nefedov SE, Beletskaya IP. J. Org. Chem. 2020; 85: 14507
• 9 Aksinenko AY, Goreva TV, Epishina TA, Martynov IV, Sokolov VB. J. Fluorine Chem. 2015; 178: 291
• 10 Huang Q, He D, Han J, Chen J, He W, Deng H, Shao M, Zhang H, Cao W. Synthesis 2018; 50: 3731
• 11a Duda B, Tverdomed SN, Röschenthaler G.-V. J. Org. Chem. 2011; 76: 71
• 11b Duda B, Tverdomed SN, Röschenthaler G.-V. Org. Biomol. Chem. 2011; 9: 8228
• 11c Alonso C, González M, Fuertes M, Rubiales G, Ezpeleta JM, Palacios F. J. Org. Chem. 2013; 78: 3858
• 11d Liu H, He D, Sun Z, He W, Han J, Chen J, Deng H, Shao M, Zhang H, Cao W. Tetrahedron 2018; 74: 135
• 11e Shen Y, Han J, Sun X, Wang X, Chen J, Deng H, Shao M, Shi H, Zhang H, Cao W. Tetrahedron 2015; 71: 4053
• 11f Wu J, Zhang H, Ding X, Tan X, Shen HC, Chen J, He W, Deng H, Song L, Cao W. J. Fluorine Chem. 2019; 220: 54
• 11g Chalyk BA, Sosedko AS, Volochnyuk DM, Tolmachev AA, Gavrilenko KS, Liashuk OS, Grygorenko OO. Org. Biomol. Chem. 2018; 16: 9152
• 12 Shen Y, Zheng J, Xin Y, Lin Y, Qi M. J. Chem. Soc., Perkin Trans. 1 1995; 997
• 13 Huang Q, Tran G, Gomez Pardo D, Tsuchiya T, Hillebrand S, Vors J.-P, Cossy J. Tetrahedron 2015; 71: 7250
• 14 Nájera C, Beletskaya IP, Yus M. Chem. Soc. Rev. 2019; 48: 4515
• 15a Nájera C, Sydnes LK, Yus M. Chem. Rev. 2019; 119: 11110
• 15b Chalyk BA, Khutorianskyi A, Lysenko A, Fil Yu, Kuchkovska YuO, Gavrilenko KS, Bakanovych Iu, Moroz YS, Gorlova AO, Grygorenko OO. J. Org. Chem. 2019; 84: 15212
• 15c Hsieh M.-T, Lin H.-C, Kuo S.-C. Tetahedron 2016; 72: 5880
• 16 Kumar V, Aggarwal R, Singh SP. Heterocycles 2008; 75: 2893
• 17a Mitrofanov AY, Nefedov SE, Beletskaya IP. Asian J. Org. Chem. 2021; 10: 2611
• 17b Mitrofanov AY, Beletskaya IP. Mendeleev Commun. 2021; 31: 536
• 17c Mitrofanov AY, Rousselin Y, Khrustalev VN, Cheprakov AV, Bessmertnykh-Lemeune A, Beletskaya IP. Eur. J. Inorg. Chem. 2019; 1300
• 17d Mitrofanov AY, Rousselin Y, Khrustalev VN, Cheprakov AV, Bessmertnykh-Lemeune A, Beletskaya IP. Eur. J. Inorg. Chem. 2019; 1313
• 17e Murashkina AV, Mitrofanov AY, Grishin YK, Rybakov VB, Beletskaya IP. ChemistrySelect 2018; 3: 6810
• 17f Mitrofanov A, Bessmertnykh-Lemeune A, Stern C, Guilard R, Gulyukina N, Beletskaya I. Synthesis 2012; 44: 3805
• 18 Singh RP, Cao G, Kirchmeier RL, Shreeve JM. J. Org. Chem. 1999; 64: 2873
• 19 Boreux A, Lonca GH, Riant O, Gagosz F. Org. Lett. 2016; 18: 5162
• 20 Bonacorso HG, Wentz AP, Lourega RV, Cechinel CA, Moraes TS, Coelho HS, Zanatta N, Martins MA. P, Hoeerner M, Alves SH. J. Fluorine Chem. 2006; 127: 1066
• 21a Hsieh M.-T, Kuo S.-C, Lin H.-C. Adv. Synth. Catal. 2015; 357: 683
• 21b Topchiy MA, Zharkova DA, Asachenko AF, Muzalevskiy VM, Chertkov VA, Nenajdenko VG, Nechaev MS. Eur. J. Org. Chem. 2018; 3750
• 22 Muzalevskiy VM, Rulev AY, Romanov AR, Kondrashov EV, Ushakov IA, Chertkov VA, Nenajdenko VG. J. Org. Chem. 2017; 82: 7200