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Synthesis 2013; 45(2): 225-230
DOI: 10.1055/s-0032-1316831
DOI: 10.1055/s-0032-1316831
paper
Synthesis of Isomeric 6-Trifluoromethyl-3-azabicyclo[3.1.0]hexanes: Conformationally Restricted Analogues of 4-Trifluoromethylpiperidine
Weitere Informationen
Publikationsverlauf
Received: 02. November 2012
Accepted after revision: 29. November 2012
Publikationsdatum:
18. Dezember 2012 (online)
Abstract
Two isomeric conformationally restricted analogues of 4-trifluoromethylpiperidine were designed. The synthesis was performed in four steps from commercially available N-benzylmaleimide. The key reaction was the [3+2] cycloaddition between trifluoromethyldiazomethane and N-benzylmaleimide.
Key words
amines - trifluoromethyl group - cyclopropane - 4-trifluoromethylpiperidine - drug designSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are copies of NMR spectra and crystallographic data for compounds 12a and 14.
- Supporting Information
-
References
- 1 Wishart DS, Knox C, Guo AC, Cheng D, Shrivastaya S, Tzur D, Gautam B, Hassanali M. Nucleic Acids Res. 2008; 36 (database issue): D.901
- 2 Roughley SD, Jordan AM. J. Med. Chem. 2011; 54: 3451
- 3a Sparey T, Beher D, Best J, Biba M, Castro JL, Clarke E, Hannam J, Harrison T, Lewis H, Madin A, Shearman M, Sohal B, Tsou N, Welch C, Wrigley J. Bioorg. Med. Chem. Lett. 2005; 15: 4212
- 3b Xin Z, Peng H, Zhang A, Talreja T, Kumaravel G, Xu L, Rohde E, Jung M, Shackett MN, Kocisko D, Chollate S, Dunah AW, Snodgrass-Belt PA, Arnold HM, Taveras AG, Rhodes KJ, Scannevin RH. Bioorg. Med. Chem. Lett. 2011; 21: 7277
- 3c Micheli F, Holmes I, Arista L, Bonanomi G, Braggio S, Cardullo F, Fabio RD, Donati D, Gentile G, Hamprecht D, Terreni S, Heidbreder C, Savoia C, Griffante C, Worby A. Bioorg. Med. Chem. Lett. 2009; 19: 4011
- 3d Lange JH. M, Neut MA.W, Hartog AP, Wals HC, Hoogendoorn J, Stuivenberg HH, Vliet BJ, Kruse CG. Bioorg. Med. Chem. Lett. 2010; 20: 1752
- 3e Keith JM, Gomez LA, Letavic MA, Ly KS, Jablonowski JA, Seierstad M, Barbier AJ, Wilson SJ, Boggs JD, Fraser IC, Mazur C, Lovenberg TW, Carruthers NI. Bioorg. Med. Chem. Lett. 2007; 17: 702
- 3f Provins L, Christophe B, Danhaive P, Dulieu J, Durieu V, Gillard M, Lebon F, Lengelé S, Quéré L, Keulen B. Bioorg. Med. Chem. Lett. 2006; 16: 1834
- 3g Bennacef I, Salinas CA, Bonasera TA, Gunn RN, Audrain H, Jakobsen S, Nabulsi N, Weinzimmer D, Carson RE, Huang Y, Holmes I, Micheli F, Heidbreder C, Gentile G, Rossi T, Laruelle M. Bioorg. Med. Chem. Lett. 2009; 19: 5056
- 3h Kerekes AD, Esposite SJ, Doll RJ, Tagat JR, Yu T, Xiao Y, Zhang Y, Prelusky DB, Tevar S, Gray K, Terracina GA, Lee S, Jones J, Liu M, Basso AD, Smith EB. J. Med. Chem. 2011; 54: 201
- 3i Woods JR, Mo H, Bieberich AA, Alavanja T, Colby DA. J. Med. Chem. 2011; 54: 7933
- 4 The search was performed in July 2012 in ‘Reaxys’ database.
- 5 The search was performed in February 2011 in ‘MDL Drug data report’ database.
- 6a Kirk KL. Org. Proc. Res. Dev. 2008; 12: 305
- 6b Filler R, Saha R. Future Med. Chem. 2009; 1: 777
- 6c Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
- 6d Hagmann WK. J. Med. Chem. 2008; 51: 4359
- 6e Böhm H.-J, Banner D, Bendels S, Kansy M, Kuhn B, Müller K, Obst-Sander U, Stahl M. ChemBioChem 2004; 5: 637
- 7a Bohm HJ. Prediction of non-bonded interactions in drug design. In Protein-Ligand Interactions. Bohm HJ, Schneider G. Wiley-VCH; Weinheim: 2003: 3
- 7b Schaeffer L. The role of functional groups in drug-receptor interactions. In The Practice of Medicinal Chemistry. 3rd ed., Wermuth CG. Academic Press/Elsevier; Amsterdam: 2008: 464
- 8a Mann A. Conformational restriction and/or steric hindrance in medicinal chemistry. In The Practice of Medicinal Chemistry. 3rd ed., Wermuth CG. Academic Press/Elsevier; Amsterdam: 2008: 363
- 8b Martin SF. Pure Appl. Chem. 2007; 79: 193
- 8c Cowell SM, Lee YS, Cain JP, Hruby VJ. Curr. Med. Chem. 2004; 11: 2785
- 8d Harrold MW. Am. J. Pharm. Educ. 1996; 60: 192
- 9a Renslo AR, Jaishankar P, Venkatachalam R, Hackbarth C, Lopez S, Patel DV, Gordeev MF. J. Med. Chem. 2005; 48: 5009
- 9b Biagetti M, Leslie CP, Mazzali A, Seri C, Pizzi DA, Bentley J, Genski T, Fabio RD, Zonzini L, Caberlotto L. Bioorg. Med. Chem. Lett. 2010; 20: 4741
- 9c Lunn G, Roberts LR, Content S, Critcher DJ, Douglas S, Fenwick AE, Gethin DM, Goodwin G, Greenway D, Greenwood S, Hall K, Thomas M, Thompson S, Williams D, Wood G, Wylie A. Bioorg. Med. Chem. Lett. 2012; 22: 2200
- 9d Lunn G, Banks BJ, Crook R, Feeder N, Pettman A, Sabnis Y. Bioorg. Med. Chem. Lett. 2011; 21: 4608
- 9e Blizzard TA, DiNinno F, Morgan JD, Chen HY, Wu JY, Gude C, Kim S, Chan W, Birzin ET, Yang YT, Pai L.-Y, Zhang Z, Hayes EC, DaSilva CA, Tang W, Rohrer SP, Schaeffer JM, Hammond ML. Bioorg. Med. Chem. Lett. 2004; 14: 3861
- 9f Blizzard TA, DiNinno F, Morgan JD, Chen HY, Wu JY, Kim S, Chan W, Birzin ET, Yang YT, Pai L.-Y, Fitzgerald PM. D, Sharma N, Li Y, Zhang Z, Hayes EC, DaSilva CA, Tang W, Rohrer SP, Schaeffer JM, Hammond ML. Bioorg. Med. Chem. Lett. 2005; 15: 107
- 9g Simpkins LM, Bolton S, Pi Z, Sutton JC, Kwon C, Zhao G, Magnin DR, Augeri DJ, Gungor T, Rotella DP, Sun Z, Liu Y, Slusarchyk WS, Marcinkeviciene J, Robertson JG, Wang A, Robl JA, Atwal KS, Zahler RL, Parker RA, Kirby MS, Hamann LG. Bioorg. Med. Chem. Lett. 2007; 17: 6476
- 9h Kaur K, Aeron S, Bruhaspathy M, Shetty SJ, Gupta S, Hegde LH, Silamkoti AD.V, Mehta A, Chugh A, Gupta JB, Sarma PK. S, Kumar N. Bioorg. Med. Chem. Lett. 2005; 15: 2093
- 10 Gootz TD, Zaniewski R, Haskell S, Schmieder B, Tankovic J, Girard D, Courvalin P, Polzer RJ. Antimicrob. Agents Chemother. 2006; 40: 2691
- 11a Artamonov OS, Mykhailiuk PK, Voievoda NM, Volochnyuk DM, Komarov IV. Synthesis 2010; 443
- 11b Atherton JH, Fields R. J. Chem. Soc. C 1968; 1507
- 12 Review on trifluoromethylcyclopropanes: Grygorenko OO, Artamonov OS, Komarov IV, Mykhailiuk PK. Tetrahedron 2011; 67: 803
- 13a Risse J, Fernandez-Zumel MA, Cudre Y, Severin K. Org. Lett. 2012; 14: 3060
- 13b Wen L, Zhang H, Lin H, Shen Q, Lu L. J. Fluorine Chem. 2012; 133: 171
- 13c Petrov VA, Marshall W. J. Fluorine Chem. 2012; 133: 61
- 13d Yarmolchuk VS, Bezdudny AV, Tolmacheva NA, Lukin O, Boyko AN, Chekotylo A, Tolmachev AA, Mykhailiuk PK. Synthesis 2012; 44: 1152
- 13e Lin H, Shen Q, Lu L. J. Org. Chem. 2011; 76: 7359
- 13f Bezdudny AV, Klukovsky D, Simurova N, Mykhailiuk PK, Shishkin OV, Pustovit YM. Synthesis 2011; 119
- 13g Wan W, Gao Y, Jiang H, Hao J. J. Fluorine Chem. 2008; 129: 510
- 13h Denton JR, Sukumaran D, Davies HM. L. Org. Lett. 2007; 9: 2625
- 13i Titanyuk ID, Beletskaya IP, Peregudov AS, Osipov SN. J. Fluorine Chem. 2007; 128: 723
- 13j Wang Y, Zhao X, Li Y, Lu L. Tetrahedron Lett. 2004; 45: 7775
- 13k Ghanem A, Lacrampe F, Aboul-Enein HY, Schurig V. Monatsh. Chem. 2005; 136: 1205
- 13l Muller P, Grass S, Shahi SP, Bernardinelli G. Tetrahedron 2004; 60: 4755
- 13m Jiang B, Zhang F, Xiong W. Chem. Commun. 2003; 536
- 13n Katagiri T, Yamaji S, Handa M, Irie M, Uneyama K. Chem. Commun. 2001; 2054
- 13o Katagiri T, Irie M, Uneyama K. Org. Lett. 2000; 2: 2423
- 13p Dmowski W, Wolniewicz A. J. Fluorine Chem. 2000; 102: 141
- 13q Katagiri T, Irie M, Uneyama K. Tetrahedron: Asymmetry 1999; 10: 2583
- 13r Bouilon J.-P, Janousek Z, Viehe HG, Tinant B, Declercq J.-P. J. Chem. Soc., Perkin Trans. 1 1996; 1853
- 13s Huisgen R, Mloston G. Tetrahedron Lett. 1989; 30: 7041
- 13t O’Bannon PE. O, Dailey WP. Tetrahedron Lett. 1989; 30: 4197
- 14a Le MauxP, Juillard S, Simonneaux G. Synthesis 2006; 1701
- 14b Mykhailiuk PK, Afonin S, Ulrich AS, Komarov IV. Synthesis 2008; 1757
- 14c Mykhailiuk PK, Afonin S, Palamarchuk GV, Shishkin OV, Ulrich AS, Komarov IV. Angew. Chem. Int. Ed. 2008; 47: 5765
- 14d Morandi B, Carreira EM. Angew. Chem. Int. Ed. 2010; 49: 938
- 14e Duncton MA. J, Ayala L, Kaub C, Janagani S, Edwards WT, Orike N, Ramamoorthy K, Kincaid J, Kelly MG. Tetrahedron Lett. 2010; 51: 1009
- 14f Villar IS, Gradillas A, Perez-Castells J. Eur. J. Org. Chem. 2010; 5850
- 14g Morandi B, Mariampillai B, Carreira EM. Angew. Chem. Int. Ed. 2011; 50: 1101
- 14h Morandi B, Cheang J, Carreira EM. Org. Lett. 2011; 13: 3080
- 15 Gilman H, Jones LG. J. Am. Chem. Soc. 1943; 65: 1458
For some recent examples, see:
For some recent reviews on this topic, see:
Some recent papers:
Selected papers on trifluoromethylcyclopropanes:
For trifluoromethylcyclopropanes obtained by metal-catalyzed trifluoromethylcyclopropanation of alkenes by CF3CHN2, see: