An Efficient Substrate-Induced Method for the Synthesis of CF3-Substituted Cyclopropanes by Metal-Free Reaction of Trifluoromethyl Styrylisoxazoles with Nitromethane

Qing-he Zhao; Guang-hao Yu; Ye-chen Meng; Feng Sui; Mi-yi Yang; Li Liu; Hui-jie Li; Feng Li; Hai Ma

doi:10.1055/s-0040-1705976

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(09): 1597-1604
DOI: 10.1055/s-0040-1705976

paper

An Efficient Substrate-Induced Method for the Synthesis of CF₃-Substituted Cyclopropanes by Metal-Free Reaction of Trifluoromethyl Styrylisoxazoles with Nitromethane

Qing-he Zhao

^aInstitute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China

,

Guang-hao Yu

^aInstitute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China

,

Ye-chen Meng

^cHengshui No. 5 Middle School, Shengli West Road, Hengshui, Hebei Province, P. R. of China

,

Feng Sui

^aInstitute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China

,

Mi-yi Yang

^aInstitute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China

,

Li Liu

^aInstitute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China

,

Hui-jie Li

^aInstitute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China

,

Feng Li∗

^bCollege of Chemistry and Chemical Engineering, Shangqiu Normal University, 298 Wenhua Road, Shangqiu, Henan 476000, P. R. of China

,

Hai Ma∗

^aInstitute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China

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Abstract

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Abstract

A series of (trifluoromethyl)cyclopropanes (TFCPs) tolerating a broad range of functional groups, known as tert-butyl bioisosteres, have been obtained from the cyclization reaction between nitromethane and 5-[β-(trifluoromethyl)styryl]isoxazoles in 70–94% yields and 75:25 to 90:10 dr. This method offers practical access to this cyclopropyl moiety of pharmacological interest, employing an inorganic base under phase-transfer conditions.

Key words

styrylisoxazole - cyclization - trifluoromethyl - cyclopropane - inorganic base - phase-transfer catalyst

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Referenzen

References
1 Lau YY, Krishna G, Yumibe NP, Grotz DE, Sapidou E, Norton L, Chu I, Chen C, Soares AD, Lin C.-C. Pharm. Res. 2002; 19: 1606

2a Pauling L. The Nature of the Chemical Bond . Cornell University Press; Ithaca: 1960
2b Bondi A. J. Phys. Chem. 1964; 68: 441

3a Themed issue on Fluorous Chemistry: Gladysz JA, Curran DP. Eds. Tetrahedron 2002; 58: 3823-4132
3b Ma J.-A, Cahard D. Chem. Rev. 2004; 104: 6119
3c Bégué JP, Bonnet-Delpon D. Bioorganic and Medicinal Chemistry of Fluorine . Wiley; Hoboken: 2008
3d Braun MG, Katcher MH, Doyle AG. Chem. Sci. 2013; 4: 1216
3e Westphal MV, Wolfstädter BT, Plancher JM, Gatfield J, Carreira EM. ChemMedChem 2015; 10: 461
3f Barnes-Seeman D, Jain M, Bell L, Ferreira S, Cohen S, Chen ZH, Amin J, Snodgrass B, Hatsis P. ACS Med. Chem. Lett. 2013; 4: 514
3g Sebhat IK, Franklin C, Lo MM.-C, Chen D, Jewell JP, Miller R, Pang J, Palyha O, Kan Y, Kelly TM, Guan X.-M, Marsh DJ, Kosinski JA, Metzger JM, Lyons K, Dragovic J, Guzzo PR, Henderson AJ, Reitman ML, Nargund RP, Wyvratt MJ, Lin LS. ACS Med. Chem. Lett. 2011; 2: 43
3h Cho EJ, Senecal TD, Kinzel K, Zhang Y, Watson DA, Buchwald SL. Science 2010; 328: 1679
3i Nagib DA, MacMillan DW. C. Nature 2011; 480: 224
3j Zeng Y, Zhang L, Zhao Y, Ni C, Zhao J, Hu J. J. Am. Chem. Soc. 2013; 135: 2955

4a Bezençon O, Heidmann B, Siegrist R, Stamm S, Richard S, Pozzi D, Corminboeuf O, Roch C, Kessler M, Ertel EA, Reymond I, Pfeifer T, de Kanter R, Toeroek-Schafroth M, Moccia LG, Mawet J, Moon R, Rey M, Capeleto B, Fournier E. J. Med. Chem. 2017; 60: 9769
4b Wityak J, McGee KF, Conlon MP, Song RH, Duffy BC, Clayton B, Lynch M, Wang G, Freeman E, Haber J, Kitchen DB, Manning DD, Ismail J, Khmelnitsky Y, Michels P, Webster J, Irigoyen M, Luche M, Hultman M, Bai M, Kuok ID, Newell R, Lamers M, Leonard P, Yates D, Matthews K, Ongeri L, Clifton S, Mead T, Deupree S, Wheelan P, Lyons K, Wilson C, Kiselyov A, Toledo-Sherman L, Beconi M, Muñoz-Sanjuan I, Bard J, Dominguez C. J. Med. Chem. 2015; 58: 2967
4c Mori T, Ujihara K, Matsumoto O, Yanagi K, Matsuo N. J. Fluorine Chem. 2007; 128: 1174
4d Lapointe BT, Fuller PH, Gunaydin H, Liu K, Sciammetta N, Trotter BW, Zhang H, Barr KJ, MacLean JK. F, Molinari D, Simov V. US 2018016239, 2018
4e Liu G, Abraham S, Liu X, Xu S, Rooks AM, Nepomuceno R, Dao A, Brigham D, Gitnick D, Insko DE, Gardner MF, Zarrinkar PP, Christopher R, Belli B, Armstrong RC, Holladay MW. Bioorg. Med. Chem. Lett. 2015; 25: 3436
4f Grygorenko OO, Artamonov OS, Komarov IV, Mykhailiuk PK. Tetrahedron 2011; 67: 803
4g Bos M, Poisson T, Pannecoucke X, Charette AB, Jubault P. Chem. Eur. J. 2017; 23: 4950

5 Le Maux P, Juillard S, Simonneaux G. Synthesis 2006; 1701

6a Morandi B, Mariampillai B, Carreira EM. Angew. Chem. Int. Ed. 2011; 50: 1101
6b Tinoco A, Steck V, Tyagi V, Fasan R. J. Am. Chem. Soc. 2017; 139: 5293
6c Li S, Cao W.-J, Ma J.-A. Synlett 2017; 28: 673
6d Kotozaki M, Chanthamath S, Fujii T, Shibatomi K, Iwasa S. Chem. Commun. 2018; 54: 5110
6e Wei Y, Tinoco A, Steck V, Fasan R, Zhang Y. J. Am. Chem. Soc. 2018; 140: 1649
6f Huang W.-S, Schlinquer C, Poisson T, Pannecoucke X, Charette AB, Jubault P. Chem. Eur. J. 2018; 24: 10339
6g Artamonov OS, Slobodyanyuk EY, Volochnyuk DM, Komarov IV, Tolmachev AA, Mykhailiuk PK. Eur. J. Org. Chem. 2014; 3592
6h Artamonov OS, Mykhailiuk PK, Voievoda NM, Volochnyuk DM, Komarov IV. Synthesis 2010; 443
6i Artamonov OS, Slobodyanyuk EY, Shishkin OV, Komarov IV, Mykhailiuk PK. Synthesis 2013; 45: 225
6j Zhu C.-L, Yang L.-J, Li S, Zheng Y, Ma J.-A. Org. Lett. 2015; 17: 3442
6k Zhu C.-L, Ma J.-A, Cahard D. Asian J. Org. Chem. 2016; 5: 66
6l Lv S, Zhou H, Yu X, Xu Y, Zhu H, Wang M, Liu H, Dai Z, Sun G, Gong X, Sun X, Wang L. Commun. Chem. 2019; 2: 69

7a Burtoloso AC. B, Dias RM. P, Leonarczyk IA. Eur. J. Org. Chem. 2013; 2013: 5005
7b Deng X.-Y, Lin J.-H, Xiao J.-C. J. Fluorine Chem. 2015; 179: 116
7c Deng X.-Y, Lin J.-H, Zheng J, Xiao J.-C. Chem. Commun. 2015; 51: 8805
7d Zheng J, Lin J.-H, Deng X.-Y, Xiao J.-C. Org. Lett. 2015; 17: 532
7e Zheng J, Lin J.-H, Yu L.-Y, Wei Y, Zheng X, Xiao J.-C. Org. Lett. 2015; 17: 6150
7f Duan Y, Zhou B, Lin J.-H, Xiao JC. Chem. Commun. 2015; 51: 13127
7g Duan Y, Lin J.-H, Xiao JC, Gu Y.-C. Org. Lett. 2016; 18: 2471
7h Hock KJ, Hommelsheim R, Mertens L, Ho J, Nguyen TV, Koenigs RM. J. Org. Chem. 2017; 82: 8220
7i Huang Q, Zheng Q, Duan Y, Lin J.-H, Xiao J.-C, Zheng X. J. Org. Chem. 2017; 82: 8273
7j Wang Z, Yang Y, Gao F, Wang Z, Luo Q, Fang L. Org. Lett. 2018; 20: 934
7k Cheng B, Zu B, Li Y, Tao C, Zhang C, Wang R, Li Y, Zhai H. Org. Biomol. Chem. 2018; 16: 3564

8a Müller P, Grass S, Shahi SP, Bernardinelli G. Tetrahedron 2004; 60: 4755
8b Wang Y, Zhu S, Zhu G, Huang Q. Tetrahedron 2001; 57: 7337
8c Denton JR, Sukumaran D, Davies HM. L. Org. Lett. 2007; 9: 2625

9a Fuchikami T, Shibata Y, Suzuki Y. Tetrahedron Lett. 1986; 27: 3173
9b Gröger C, Musso H, Roßnagel I. Chem. Ber. 1980; 113: 3621

10 Phelan JP, Lang SB, Compton JS, Kelly CB, Dykstra R, Gutierrez O, Molander GA. J. Am. Chem. Soc. 2018; 140: 8037

11a Zhang H, Barr KJ, Lapointe BT, Gunaydin H, Liu K, Trotter BW. WO 2017075185, 2017
11b Winter M, Gaunersdorfer C, Roiser L, Zielke K, Monkowius U, Waser M. Eur. J. Org. Chem. 2018; 2018: 418
11c Allgäuer DS, Jangra H, Asahara H, Li Z, Chen Q, Zipse H, Ofial AR, Mayr H. J. Am. Chem. Soc. 2017; 139: 13318
11d Riches SL, Saha C, Fontán Filgueira N, Grange E, McGarrigle EM, Aggarwal VK. J. Am. Chem. Soc. 2010; 132: 7626

12a Mercadante MA, Kelly CB, Hamlin TA, Delle Chiaie KR, Drago MD, Duffy KK, Dumas MT, Fager DC, Glod BL. C, Hansen KE, Hill CR, Leising RM, Lynes CL, MacInnis AE, McGohey MR, Murray SA, Piquette MC, Roy SL, Smith RM, Sullivan KR, Truong BH, Vailonis KM, Gorbatyuk V, Leadbeater NE, Tilley LJ. Chem. Sci. 2014; 5: 3983
12b Kelly CB, Mercadante MA, Carnaghan ER, Doherty MJ, Fager DC, Hauck JJ, MacInnis AE, Tilley LJ, Leadbeater NE. Eur. J. Org. Chem. 2015; 2015: 4071

13a Zhang Y, Wei B.-W, Lin H, Zhang L, Liu J.-X, Luo H.-Q, Fan X.-L. Green Chem. 2015; 17: 3266
13b Zhang Y, Wei B.-W, Zou L.-N, Kang M.-L, Luo H.-Q, Fan X.-L. Tetrahedron 2016; 72: 2472

14a Xie J.-W, Wang Z, Yang W.-J, Kong L.-C, Xu D.-C. Org. Biomol. Chem. 2009; 7: 4352
14b Chen Z, Zheng Y, Ma J.-A. Angew. Chem. Int. Ed. 2017; 56: 4569
14c Kashihara M, Yadav MR, Nakao Y. Org. Lett. 2018; 20: 1655
14d Ouyang K, Hao W, Zhang W.-X, Xi Z. Chem. Rev. 2015; 115: 12045

15 CCDC 1574943 (2i) contains 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.
16 Kawai H, Yuan Z, Kitayama T, Tokunaga E, Shibata N. Angew. Chem. Int. Ed. 2013; 52: 5575

18a Del Fiandra C, Piras L, Fini F, Disetti P, Moccia M, Adamo MF. A. Chem. Commun. 2012; 48: 3863
18b Moccia M, Wells RJ, Adamo MF. A. Org. Biomol. Chem. 2015; 13: 2192

19 Baschieri A, Bernardi L, Ricci A, Suresh S, Adamo MF. A. Angew. Chem. Int. Ed. 2009; 48: 9342

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