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Synlett 2012; 23(20): 2961-2964
DOI: 10.1055/s-0032-1317685
DOI: 10.1055/s-0032-1317685
letter
Iron(II)-Catalyzed Denitration Reaction: Synthesis of 3-Methyl-2-arylimidazo[1,2-a]pyridine Derivatives from Aminopyridines and 2-Methylnitroolefins
Further Information
Publication History
Received: 04 September 2012
Accepted after revision: 31 October 2012
Publication Date:
27 November 2012 (online)
Abstract
A variety of ways to synthesize imidazo[1,2-a]pyridines have been reported and many approaches are devoted to the functionalization of imidazo[1,2-a]pyridines. However, the use of a denitration reaction in the synthesis of imidazo[1,2-a]pyridines has not been reported. We report here the iron-catalyzed synthesis of 3-methyl-2-arylimidazo [1,2-a] pyridine derivatives from aminopyridines and 2-methyl-nitroolefins. The procedure, using FeCl2 as catalyst, is simple and inexpensive. Various functional groups are tolerated and provide the products in good yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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References and Notes
- 1a Chattopadhyay B, Gevorgyan V. Angew. Chem. Int. Ed. 2012; 51: 862
- 1b Burchak ON, Mugherli L, Ostuni M, Lacapere JJ, Balakirev MY. J. Am. Chem. Soc. 2011; 133: 10058
- 1c Bonne D, Dekhane M, Zhu JP. Angew. Chem. Int. Ed. 2007; 46: 2485
- 1d Zhou HY, Zhang W, Yan B. J. Comb. Chem. 2010; 12: 206
- 1e Wei HL, Yan ZY, Niu YL, Li GQ, Liang YM. J. Org. Chem. 2007; 72: 8600
- 1f Jiang B, Rajale T, Wever W, Tu SJ, Li GG. Chem.–Asian J. 2010; 5: 2318
- 1g Hong D, Zhu YX, Li Y, Lin XF, Lu P, Wang YG. Org. Lett. 2011; 13: 4668
- 1h Basso A, Banfi L, Riva R. Eur. J. Org. Chem. 2010; 1831
- 1i Lin XF, Mao ZJ, Dai XX, Lu P, Wang YG. Chem. Commun. 2011; 47: 6620
- 1j Rousseau AL, Matlaba P, Parkinson CJ. Tetrahedron Lett. 2007; 48: 4079
- 1k Dömling A. Chem. Rev. 2006; 106: 17
- 1l Zhu J. Eur. J. Org. Chem. 2003; 1133
- 2a Rupert KC, Henry JR, Dodd JH, Wadsworth SA, Cavender DE, Olini GC, Fahmy B, Siekierka JJ. Bioorg. Med. Chem. Lett. 2003; 13: 347
- 2b Moraski GC, Markley LD, Hipskind PA, Boshoff H, Cho S, Franzblau SG, Miller MJ. ACS Med. Chem. Lett. 2011; 2: 466
- 3 Bae JS, Lee DW, Lee DH, Jeong DS. PCT Int. Appl WO2007011163A1, 2007
- 4 Hsua N, Jha SK, Coleman T, Frank MG. Behav. Brain Res. 2009; 201: 233
- 5 Gueiffier EC, Gueiffier A. Mini-Rev. Med. Chem. 2007; 7: 888
- 6a Harrison TS, Keating GM. CNS Drugs 2005; 19: 65
- 6b Katritzky AR, Xu YJ, Tu H. J. Org. Chem. 2003; 68: 4935
- 7 Hanson SM, Morlock EV, Satyshur KA, Czajkowski C. J. Med. Chem. 2008; 51: 7243
- 8 Rival Y, Grassy G, Taudou A, Ecalle R. Eur. J. Med. Chem. 1991; 26: 13
- 9 Hamdouchi C, de Blas J, del Prado M, Gruber J, Heinz BA, Vance L. J. Med. Chem. 1999; 42: 50
- 10a Badaway E, Kappe T. Eur. J. Med. Chem. 1995; 30: 327
- 10b Hranjec M, Piantanida I, Kralj M, Suman L, Pavelıć K, Karminski-Zamola G. J. Med. Chem. 2008; 51: 4899
- 10c Hranjec M, Kralj M, Piantanida I, Sedıć M, Suman L, Pavelıć K, Karminski-Zamola G. J. Med. Chem. 2007; 50: 5696
- 11a Gueiffier A, Lhassani M, Elhakmaoui A, Snoeck R, Andrei G, Chaxignon O, Teulade JC, Kerbal A, Essassi EM, Debouzy JC, Witvrouw M, Blache Y, Balzarini J, De Clercq E, Chapat JP. J. Med. Chem. 1996; 39: 2856
- 11b Lhassani M, Chavignon O, Chezal JM, Teulade JC, Chapat JP, Snoeck R, Andrei G, Balzarini J, De Clercq E, Gueiffier A. Eur. J. Med. Chem. 1999; 34: 271
- 11c Gueiffier A, Mavel S, Lhassani M, Elhakmaoui A, Snoeck R, Andrei G, Chavignon O, Teulade JC, Witvrouw M, Balzarini J, De Clercq E, Chapat JP. J. Med. Chem. 1998; 41: 5108
- 12a Fisher MH, Lusi A. J. Med. Chem. 1972; 15: 982
- 12b Teulade JC, Grassy G, Girard JP, Chapat JP. Eur. J. Med. Chem. 1978; 13: 271
- 13a Biftu T, Feng D, Fisher M, Liang GB, Qian X, Scribner A, Dennis R, Lee S, Liberator PA, Brown C, Gurnett A, Leavitt PS, Thompson D, Mathew J, Misura A, Samaras S, Tamas T, Sina JF, McNulty KA, McKnight CG, Schmatz DM, Wyvratt M. Bioorg. Med. Chem. Lett. 2006; 16: 2479
- 13b Scribner A, Dennis R, Lee S, Ouvry G, Perrey D, Fisher M, Wyvratt M, Leavitt P, Liberator P, Gurnett A, Brown C, Mathew J, Thompson D, Schmatz D, Biftu T. Eur. J. Med. Chem. 2008; 43: 1123
- 14 Almirante L, Polo L, Mugnaini A, Provinciali E, Rugarli P, Biancotti A, Gamba A, Murmann W. J. Med. Chem. 1965; 8: 305
- 15a Cheng D, Croft L, Abdi M, Lightfoot A, Gallagher T. Org. Lett. 2007; 9: 5175
- 15b Frohn MJ, Hong FT, Liu L, Lopez P, Siegmund AC, Tadesse S, Tamayo N. PCT Int. Appl WO2005070932, 2005
- 16 Enguehard-Gueiffier C, Fauvelle F, Debouzy JC, Peinnequin A, Thery I, Dabouis V, Gueiffier A. Eur. J. Pharm. Sci. 2005; 24: 219
- 17 Bartholini G. L.E.R.S. Monogr. Ser. 1993; 8: 1 ; Chem. Abstr. 1996, 124, 164079n
- 18a Barun O, Ila H, Junjappa H. J. Org. Chem. 2000; 65: 1583
- 18b Denora N, Laquintana V, Pisu MG, Dore R, Murru L, Latrofa A, Trapani G, Sanna E. J. Med. Chem. 2008; 51: 6876
- 18c Yan B, Liu Y. Org. Lett. 2007; 9: 3433
- 18d Trapani G, Laquintana V, Denora N, Trapani A, Lopedota A, Latrofa A, Franco M, Serra M, Pisu MG, Floris I, Sanna E, Biggio G, Liso G. J. Med. Chem. 2005; 48: 292
- 18e Masquelin T, Bui H, Brickley B, Stephenson G, Schwerkosked J, Hulmea C. Tetrahedron Lett. 2006; 47: 2989
- 18f Fookes CJ. R, Pham TQ, Mattner F, Greguric I, Loc’h C, Liu X, Berghofer P, Shepherd R, Gregoire MC, Katsifis A. J. Med. Chem. 2008; 51: 3700
- 18g Laquintana V, Denora N, Lopedota A, Suzuki H, Sawada M, Serra M, Biggio G, Latrofa A, Trapani G, Liso G. Bioconjugate Chem. 2007; 18: 1397
- 18h Basavaiah D, Devendar B, Lenin DV, Satyarayana T. Synlett 2009; 411
- 18i Loones KT. J, Maes BU. W, Meyers C, Deruytter J. J. Org. Chem. 2006; 71: 260
- 19a Chernyak N, Gevorgyan V. Angew. Chem. Int. Ed. 2010; 49: 2743
- 19b Mishra S, Ghosh R. Synthesis 2011; 3463
- 19c Dömling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168
- 20a Wang H, Wang Y, Liang D, Liu L, Zhang J, Zhu Q. Angew. Chem. Int. Ed. 2011; 50: 5678
- 20b Wang H, Wang Y, Peng C, Zhang J, Zhu Q. J. Am. Chem. Soc. 2010; 132: 13217
- 20c Guan ZH, Li L, Ren ZH, Li J, Zhao MN. Green Chem. 2011; 13: 1664
- 20d Masters KS, Rauws TR. M, Yasav AK, Herrebout WA, Veken BV, Mases BU. W. Chem.–Eur. J. 2011; 17: 6315
- 20e Lahoz IR, Sicre C, Navarro-Vazquez A, Lopez CS, Cid MM. Org. Lett. 2009; 11: 4802
- 21a Ma L, Wang X, Yu W, Han B. Chem. Commun. 2011; 47: 11333
- 21b Collins MR, Huang QH, Ornelas MA, Scales SA. Tetrahedron Lett. 2010; 51: 3528
- 21c DiMauro EF, Kennedy JM. J. Org. Chem. 2007; 72: 1013
- 21d Dai WX, Petersen JL, Wang KK. J. Org. Chem. 2005; 70: 6647
- 22a Yan R, Huang J, Luo J, Wen P, Huang G, Liang Y. Synlett 2010; 1071
- 22b Yan RL, Luo J, Wang CX, Ma CW, Huang GS, Liang YM. J. Org. Chem. 2010; 75: 5395
- 22c Yan RL, Yan H, Ma C, Ren ZY, Gao XA, Huang GS, Liang YM. J. Org. Chem. 2012; 77: 2024
- 22d Yan H, Yan R, Yang S, Gao X, Wang Y, Huang G, Liang Y. Chem.–Asian J. 2012; 7: 2028
- 23 Typical Procedure for the Preparation of 3-Methyl-2-arylimidazo[1,2-a]pyridine: A test tube was charged with 1a (0.34 mmol), 2a (0.41 mmol) and FeCl2 (3.81 mg, 0.03 mmol). Then DMF (2 mL) was added to the reaction system. The reaction was stirred at 150 °C for 7 h. After cooling to r.t., the solvent was diluted with EtOAc (10 mL) and washed with brine (5 mL) and dried over anhyd Na2SO4. After the solvent was evaporated in vacuo, the residues were purified by column chromatography, eluting with PE–EtOAc to afford pure 3aa (57 mg, 80%) as a white solid; mp 140–142 °C. 1H NMR (400 MHz, CDCl3): δ = 7.78–7.84 (m, 3 H), 7.62 (d, J = 9.2 Hz, 1 H), 7.45 (t, J = 7.6 Hz, 2 H), 7.31–7.34 (m, 1 H), 7.11–7.15 (m, 1 H), 6.78 (t, J = 6.8 Hz, 1 H), 2.58 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 144.2, 142.2, 134.7, 128.3, 128.2, 127.2, 123.3, 122.7, 117.2, 115.7, 111.8, 9.45. IR (neat): 3066, 3030, 2918, 1501, 1354, 1246, 773, 753, 700 cm–1. HRMS (ESI): m/z [M + H]+ calcd for C14H13N2: 209.1073; found: 209.1077.