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Synthesis 2012; 44(13): 2041-2048
DOI: 10.1055/s-0031-1291126
DOI: 10.1055/s-0031-1291126
paper
A Convenient Synthesis of (1H-Azol-1-yl)piperidines
Weitere Informationen
Publikationsverlauf
Received: 22. März 2012
Accepted after revision: 18. April 2012
Publikationsdatum:
31. Mai 2012 (online)
Abstract
A convenient preparation of 3- and 4-(1H-azol-1-yl)piperidines by arylation of azoles (i.e., pyrazoles, imidazoles, and triazoles) with 3- and 4-bromopyridines and subsequent reduction of the pyridine ring was developed. The method was extended to benzo analogues of the title compounds.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1a Lovering F, Bikker J, Humblet C. J. Med. Chem. 2009; 52: 6752
- 1b Kingwell K. Nat. Rev. Drug Discovery 2009; 8: 931
- 1c Nicholls A, McGaughey GB, Sheridan RP, Good AC, Warren G, Mathieu M, Muchmore SW, Brown SP, Grant JA, Haigh JA, Nevins N, Jain AN, Kelley B. J. Med. Chem. 2010; 53: 3862
- 1d Feher M, Schmidt JM. J. Chem. Inf. Comput. Sci. 2003; 43: 218
- 2a Kombarov R, Altieri A, Genis D, Kirpichenok M, Kochubey V, Rakitina N, Titarenko Z. Mol. Diversity 2010; 14: 193
- 2b Würdemann M, Christoffers J. Synlett 2011; 2841
- 3 Wink M In Modern Alkaloids: Structure, Isolation, Synthesis and Biology . Fattorusso E, Taglialatela-Scafati O. Wiley–VCH; Weinheim: 2008
- 4 Cui JJ, Tran-Dube M, Shen H, Nambu M, Kung P.-P, Pairish M, Jia L, Meng J, Funk L, Botrous I, McTigue M, Grodsky N, Ryan K, Padrique E, Alton G, Timofeevski S, Yamazaki S, Li Q, Zou H, Christensen J, Mroczkowski B, Bender S, Kania RS, Edwards MP. J. Med. Chem. 2011; 54: 6342
- 5 Katz JD, Jewell JP, Guerin DJ, Lim J, Dinsmore CJ, Falcone D, Gabarda AE, Holmes R, Mathvink R, Spencer KB, Young J, Pan B.-S, Marshall CG, Lu W, Davis L, Hang G, Hatch H, Lutterbach B, Dahlberg WK, Rosenstein C, Szewczak AA, Wang W, Altman MD, Kunii K, Qu X, Reilly JF, Deshmukh SV, Nazef N, Zeng Q, Walker D, Lumb KJ, Patel SB, Rickert KW, Soisson SM. J. Med. Chem. 2011; 54: 4092
- 6 Cho SY, Han S.-Y, Ha JD, Ryu JW, Lee CO, Jung H, Kang NS, Kim HR, Koh JS, Lee J. Bioorg. Med. Chem. Lett. 2010; 20: 4223
- 7 Shen D.-M, Shu M, Mills SG, Chapman KT, Malkowitz L, Springer MS, Gould SL, DeMartino JA, Siciliano SJ, Kwei GY, Carella A, Carver G, Holmes K, Schleif WA, Danzeisen R, Hazuda D, Kessler J, Lineberger J, Miller MD, Emini EA. Bioorg. Med. Chem. Lett. 2004; 14: 935
- 8 Barber CG, Blakemore DC, Chiva J.-Y, Eastwood RL, Middleton DS, Paradowski KA. Bioorg. Med. Chem. Lett. 2009; 19: 1499
- 9 Lam PY. S, Clark CG, Li R, Pinto DJ. P, Orwat MJ, Galemmo RA, Fevig JM, Teleha CA, Alexander RS, Smallwood AM, Rossi KA, Wright MR, Bai SA, He K, Luettgen JM, Wong PC, Knabb RM, Wexler RR. J. Med. Chem. 2003; 46: 4405
- 10a Zhang D, Kohlman D, Krushinski J, Liang S, Ying B.-P, Reilly JE, Dinn SR, Wainscott DB, Nutter S, Gough W, Nelson DL. G, Schaus JM, Xu YC. Bioorg. Med. Chem. Lett. 2004; 14: 6011
- 10b Allerton CM. N, Barber CG, Beaumont KC, Brown DG, Cole SM, Ellis D, Lane CA. L, Maw GN, Mount NM, Rawson DJ, Robinson CM, Street SD. A, Summerhill NW. J. Med. Chem. 2006; 49: 3581
- 10c Newhouse BJ, Hansen JD, Grina J, Welch M, Topalov G, Littman N, Callejo M, Martinson M, Galbraith S, Laird ER, Brandhuber BJ, Vigers G, Morales T, Woessner R, Randolph N, Lyssikatos J, Olivero A. Bioorg. Med. Chem. Lett. 2011; 21: 3488
- 10d Moore KW, Bonner K, Jones EA, Emms F, Leeson PD, Marwood R, Patel S, Patel S, Rowley M, Thomas S, Carling RW. Bioorg. Med. Chem. Lett. 1999; 9: 1285
- 10e Coon T, Moree WJ, Li B, Yu J, Zamani-Kord S, Malany S, Santos MA, Hernandez LM, Petroski RE, Sun A, Wen J, Sullivan S, Haelewyn J, Hedrick M, Hoare SJ, Bradbury MJ, Crowe PD, Beaton G. Bioorg. Med. Chem. Lett. 2009; 19: 4380
- 11a Ranatunge RR, Augustyniak M, Bandarage UK, Earl RA, Ellis JL, Garvey DS, Janero DR, Letts LG, Martino AM, Murty MG, Richardson SK, Schroeder JD, Shumway MJ, Tam SW, Trocha AM, Young DV. J. Med. Chem. 2004; 47: 2180
- 11b Traquandi G, Ciomei M, Ballinari D, Casale E, Colombo N, Croci V, Isacchi A, Longo A, Panzeri A, Pastori W, Volpi D, Brasca MG, Fiorentini F, Mercurio C, Pevarello P, Roussel P, Vulpetti A. J. Med. Chem. 2010; 53: 2171
- 11c Takahashi H, Shinoyama M, Komine T, Tsuchida H, Katsuyama K, Nagao M, Suzuki M. Bioorg. Med. Chem. Lett. 2011; 21: 1758
- 11d Nagarajan K, Arya VP, Shenoy SJ. J. Chem. Res., Miniprint 1986; 1401
- 11e Arya VP, Grewal RS, Kaul CL, Ghate SP, Mehta DV, George T. J. Pharm. Sci. 1969; 58: 432
- 11f Hoehn H. Z. Chem. 1970; 10: 386
- 12a Bressi JC, de Jong R, Wu Y, Jennings AJ, Brown JW, O’Connell S, Tari LW, Skene RJ, Vu P, Navre M, Cao X, Gangloff AR. Bioorg. Med. Chem. Lett. 2010; 20: 3138
- 12b Sisko J, Kassick AJ, Mellinger M, Filan JJ, Alien A, Olsen MA. J. Org. Chem. 2000; 65: 1516
- 12c de Dios A, Shih C, de Uralde BL, Sanchez C, del Prado M, Cabrejas LM. M, Pleite S, Blanco-Urgoiti J, Lorite MJ, Nevill CR, Bonjouklian R, York J, Vieth M, Wang Y, Magnus N, Campbell RM, Anderson BD, McCann DJ, Giera DD, Lee PA, Schultz RM, Li LC, Johnson LM, Wolos JA. J. Med. Chem. 2005; 48: 2270
- 12d Laufer SA, Zimmermann W, Ruff KJ. J. Med. Chem. 2004; 47: 6311
- 12e Dombroski MA, Letavic MA, McClure KF, Barberia JT, Carty TJ, Cortina SR, Csiki C, Dipesa AJ, Elliott NC, Gabel CA, Jordan CK, Labasi JM, Martin WH, Peese KM, Stock IA, Svensson L, Sweeney FJ, Yu CH. Bioorg. Med. Chem. Lett. 2004; 14: 919
- 12f Gallagher TF, Seibel GL, Kassis S, Laydon JT, Blumenthal MJ, Lee JC, Lee D, Boehm JC, Fier-Thompson SM, Abt JW, Soreson ME, Smietana JM, Hall RF, Garigipati RS, Bender PE, Erhard KF, Krog AJ, Hofmann GA, Sheldrake PL, McDonnell PC, Kumar S, Young PR, Adams JL. Bioorg. Med. Chem. 1997; 5: 49
- 12g Boehm JC, Bower MJ, Gallagher TF, Kassis S, Johnson SR, Adams JL. Bioorg. Med. Chem. Lett. 2001; 11: 1123
- 12h Adams JL, Boehm JC, Gallagher TF, Kassis S, Webb EF, Hall R, Sorenson M, Garigipati R, Griswold DE, Lee JC. Bioorg. Med. Chem. Lett. 2001; 11: 2867
- 13 Imaeda Y, Kuroita T, Sakamoto H, Kawamoto T, Tobisu M, Konishi N, Hiroe K, Kawamura M, Tanaka T, Kubo K. J. Med. Chem. 2008; 51: 3422
- 15 Sperotto E, van Klink GP. M, van Koten G, de Vries JG. Tetrahedron 2010; 66: 3478
- 16 Chen H, Huang W, Wang D, Cai Q, Ding K, Wang X. Synthesis 2010; 1505
- 17a Zhang Z, Mao J, Zhu D, Wu F, Chen H, Wan B. Tetrahedron 2006; 62: 4435
- 17b Paradies J. Synthesis 2011; 3749
- 18 Wu X.-M, Wang Y. J. Chem. Res., Synop. 2009; 555
- 19 Cristau H.-J, Cellier PP, Spindler J.-F, Taillefer M. Eur. J. Org. Chem. 2004; 695
- 20 Chevallier F, Pecceu C, Nassar IF, Dam TU, Mongin F, Halauko YS, Roisnel T, Matulis VE, Ivashkevich OA. Org. Biomol. Chem. 2011; 9: 4671
- 21 Liu Z.-J, Bolm C, Vors J.-P, Gesing ER. F. Green Chem. 2011; 13: 42
MissingFormLabel
- 22 Liu Z.-J, Bolm C, Vors J.-P, Gesing ER. F. Adv. Synth. Catal. 2010; 352: 3158
- 23 Antilla JC, Baskin JM, Barder TE, Buchwald SL. J. Org. Chem. 2004; 69: 5578
- 24 Nakada Y, Kitamura S, Miki H, Yamamoto T, Yamaguchi H, Kato K, Aicher TD, Huerou YL, Turner T, Pratt SA, Gonzales SS, Boyd SA. Bioorg. Med. Chem. 2010; 18: 2785
- 25 Kantam ML, Venkanna GT, Sridhar C, Kumar KB. S. Tetrahedron Lett. 2006; 47: 3897
- 26 Guillou S, Bonhomme FJ, Chahine DB, Nesme O, Janin YL. Tetrahedron 2010; 66: 2654
- 27 Altman RA, Koval ED, Buchwald SL. J. Org. Chem. 2007; 72: 6190
- 28 Kauffmann T, Tigler D, Woltermann A. Chem. Ber. 1982; 115: 452
- 29 Denton TT, Zhang X, Cashman JR. J. Med. Chem. 2005; 48: 224
MissingFormLabel
- 30 Cano R, Ramon DJ, Yus M. J. Org. Chem. 2011; 76: 654
- 31 Keith JM. J. Org. Chem. 2010; 75: 2722
MissingFormLabel
- 32 Son SU, Park IK, Park J, Hyeon T. Chem. Commun. 2004; 778
- 33 Khan MA, Polya JB. J. Chem. Soc. C 1970; 85