Synlett 2012; 23(18): 2603-2608
DOI: 10.1055/s-0032-1317329
letter
© Georg Thieme Verlag Stuttgart · New York

Transition-Metal-Catalyzed Arylation of 1-Deazapurines via C–H Bond Activation

Viktor O. Iaroshenko*
a   Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany   Fax: +49(381)49864112   Email: viktor.iaroshenko@uni-rostock.de   Email: iva108@googlemail.com
b   National Taras Shevchenko University, 62 Volodymyrska st., Kyiv-33, 01033, Ukraine
,
Iftikhar Ali
a   Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany   Fax: +49(381)49864112   Email: viktor.iaroshenko@uni-rostock.de   Email: iva108@googlemail.com
,
Satenik Mkrtchyan
a   Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany   Fax: +49(381)49864112   Email: viktor.iaroshenko@uni-rostock.de   Email: iva108@googlemail.com
,
Volodymyr Semeniuchenko
b   National Taras Shevchenko University, 62 Volodymyrska st., Kyiv-33, 01033, Ukraine
,
Dmytro Ostrovskyi
a   Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany   Fax: +49(381)49864112   Email: viktor.iaroshenko@uni-rostock.de   Email: iva108@googlemail.com
,
Peter Langer
a   Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany   Fax: +49(381)49864112   Email: viktor.iaroshenko@uni-rostock.de   Email: iva108@googlemail.com
c   Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
› Author Affiliations
Further Information

Publication History

Received: 02 August 2012

Accepted after revision: 06 September 2012

Publication Date:
01 October 2012 (online)


Abstract

Transition-metal-catalyzed arylation of imidazo[4,5-b]pyridines (known as 1-deazapurines) is reported. 1-Deazapurines were synthesized from 5-aminoimidazoles, generated in situ by the reaction of methyl N-(cyanomethyl)formimidate with primary amines.

Supporting Information

 
  • References

    • 1a Vittori S, Dal Ben D, Lambertucci C, Marucci G, Volpini RCristalli G. Curr. Med. Chem. 2006; 13: 3529
    • 1b Dubey PK, Kumar RV, Naidu A, Kulkarni SM. Asian J. Chem. 2002; 14: 1129
    • 1c Mederski WW. K. R. K, Pacher GR. Tetrahedron 1992; 48: 10549
    • 1d Middleton RW, Wibberley DG. J. Heterocycl. Chem. 1980; 17: 1757
    • 1e Bukowski L, Janowiec M. Pharmazie 1988; 43: 315
    • 1f Chakravarty PK, Naylor EM, Chen A, Chang RS. L, Chen T.-B, Faust KA, Lotti VJ, Kivlighn SD, Gable RA. J. Med. Chem. 1994; 37: 4068
  • 2 Joseph EC, Rees JA, Dayan AD. Toxicol. Pathology 1996; 24: 436
  • 3 Ida K, Otsubo N, Kuboyama T, Arai H, Watanabe A, Saki M, Hiura N, Manabe H, Tekada H, Saito J. WO2005082905, 2005 ; Chem. Abstr. 2005, 143, 266925
    • 4a Bavetsias V, Sun C, Bouloc N, Reynisson J, Workman P, Linardopoulos S, McDonald E. Bioorg. Med. Chem. Lett. 2007; 17: 6567
    • 4b Chan F, Sun C, Perumal M, Nguyen Q.-D, Bavetsias V, McDonald E, Martins V, Wilsher NE, Raynaud MValenti S, Eccles R, te Poele P, Workman FI, Aboagye EO, Linardopoulos S. Mol. Cancer Ther. 2007; 6: 3147
    • 5a Rizzo M, Ventrice D, Monforte F, Procopio S, De Sarro G, Anzini M, Cappelli A, Makovec F. J. Pharm. Biomed. Anal. 2004; 35: 321
    • 5b Rizzo M, Anzini M, Cappelli A, Vomero S, Ventrice D, De Sarro G, Procopio S, Costa N, Makovec F. Farmaco 2003; 58: 837
    • 5c Casimiro-Garcia A, Filzen GF, Flynn D, Bigge CF, Chen J, Davis JA, Dudley DA, Edmunds JJ, Esmaeil N, Geyer A, Heemstra RJ, Jalaie M, Ohren JF, Ostroski R, Ellis T, Schaum RP, Stoner C. J. Med. Chem. 2011; 54: 4219
    • 5d Wexler RR, Greenlee WJ, Irvin JD, Goldberg MR, Prendergast K, Smith RD, Timmermans PB. M. W. M. J. Med. Chem. 1996; 39: 625
    • 5e Mantlo NB, Chakravarty PK, Ondeyka DL, Siegl PK. S, Chang RS, Lotti VJ, Faust KA, Schorn TW, Chen TB. J. Med. Chem. 1991; 34: 2919
    • 5f Kim D, Mantlo NB, Chang RS. L, Kivlighn SD, Greenlee WJ. Bioorg. Med. Chem. Lett. 1994; 4: 41
    • 5g Mantlo NB, Chang RS. L, Siegl PK. S. Bioorg. Med. Chem. Lett. 1993; 3: 1693
    • 6a Cristalli G, Vittori S, Eleuteri A, Grifantini M, Volpini R, Lupidi G, Capolongo L, Pesenti E. J. Med. Chem. 1991; 34: 2226
    • 6b Bergman AM, Cristalli G, Vittori S, Wang J, Eriksson S, Peters G. Nucleosides Nucleotides 1999; 18: 897
  • 7 Bennett LJr, Smithers D, Rose LM, Adamson DJ, Brockman RW. Biochem. Pharmacol. 1984; 33: 261
  • 8 Clark RL, Pessolano AA, Shen T.-Y, Jacobus DP, Jones H, Lotti VJ, Flataker LM. J. Med. Chem. 1978; 21: 965
    • 9a Hocková D, Hocek M, Dvoráková H, Votruba I. Tetrahedron 1999; 55: 11109
    • 9b Kuczynski L, Mrozikiewicz A, Poreba K. Pol. J. Pharmacol. Pharm. 1982; 34: 229
    • 9c Bianchi M, Butti A, Rossi S, Barzaghi F, Marcaria V. Eur. J. Med. Chem. 1983; 18: 501
    • 9d Ostrovskyi D, Iaroshenko VO, Ali I, Mkrtchyan S, Villinger A, Tolmachev A, Langer P. Synthesis 2011; 133 ; and references therein
    • 10a Kimoto M, Moriyama K, Yokoyama S, Hirao I. Bioorg. Med. Chem. Lett. 2007; 17: 5582
    • 10b Service RF. Science 2000; 289: 232
  • 11 Burnstock G. Nat. Rev. Drug Discovery 2008; 7: 575
  • 12 Chu CK. Recent Advances in Nucleosides: Chemistry and Chemotherapy. Elsevier; Amsterdam: 2002
    • 13a Montgomery JA, Clayton SJ, Thomas HJ, Shannon WM, Arnett G, Bodner AJ, Kion IK, Cantoni GL, Chiang PK. J. Med. Chem. 1982; 25: 626
    • 13b Tseng CK. H, Marquez VE, Fuller RW, Goldstein BM, Haines DR, McPherson H, Parsons JL, Shannon WM, Arnett G. J. Med. Chem. 1989; 32: 1442
    • 13c Yutilov YM. Adv. Heterocycl. Chem. 2005; 89: 159
    • 14a Suhadolnik RJ In Nucleoside Antibiotics . Suhadolnik RJ. Wiley-Interscience; New York: 1970: 298-353
    • 14b Uhlmann E, Peyman A. Chem. Rev. 1990; 90: 543
    • 14c Seela F, Budow S, Peng X. Curr. Org. Chem. 2012; 16: 161
    • 15a Schlosser M. Angew. Chem. Int. Ed. 2006; 45: 5432
    • 15b Shimizu M, Hiyama T. Angew. Chem. Int. Ed. 2005; 44: 214
    • 15c Resnati G. Tetrahedron 1993; 49: 9385
    • 15d Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
    • 15e Filler R, Kobayashi Y, Yagupolskii LM. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications. Elsevier; Amsterdam: 1993
    • 16a Iaroshenko VO, Mkrtchyan S, Gevorgyan A, Vilches-Herrera M, Sevenard DV, Villinger AT, Ghochikyan V, Saghiyan A, Sosnovskikh VY, Langer P. Tetrahedron 2012; 68: 2532
    • 16b Iaroshenko VO, Mkrtchyan S, Ghazaryan G, Hakobyan A, Maalik A, Supe L, Villinger A, Tolmachev A, Ostrovskyi D, Sosnovskikh VY, Ghochikyan TV, Langer P. Synthesis 2011; 469
    • 16c Iaroshenko VO, Ostrovskyi D, Petrosyan A, Mkrtchyan S, Villinger A, Langer P. J. Org. Chem. 2011; 76: 2899
    • 16d Iaroshenko VO, Sevenard DV, Kotljarov A, Volochnyuk DM, Tolmachev AO, Sosnovskikh VY. Synthesis 2009; 731
    • 16e Iaroshenko VO, Specowius V, Vlach K, Vilches-Herrera M, Ostrovskyi D, Mkrtchyan S, Villinger A, Langer P. Tetrahedron 2011; 67: 5663
    • 16f Ostrovskyi D, Iaroshenko VO, Petrosyan A, Dudkin S, Ali I, Villinger A, Tolmachev A, Langer P. Synlett 2010; 2299
    • 17a Post MJ, te Biesebeek JD, Wemer J, van Rooij HH, Porsius AJ. Pulm. Pharmacol. 1991; 4: 239
    • 17b Weishaar RE, Bristol JA. Comprehensive Medicinal Chemistry . Vol. 2. Hansch C, Sammes PG, Taylor JB. Pergamon Press; Oxford: 1990: 501-514
    • 17c Koch H. Pharm. Int. 1982; 3: 5
    • 18a Diederen W, Kadatz R. Arzneim.-Forsch. 1981; 31: 141
    • 18b Hayes JS, Wyss VL, Wilson HC. D, Robertson W, Kauffman RF. J. Pharmacol. Exp. Ther. 1986; 239: 375
    • 18c McGarry SJ, Williams AJ. Br. J. Pharmacol. 1994; 111: 1212
    • 18d Honerjaeger P, Klockow M, Schoensteiner G, Jonas R. J. Cardiovasc. Pharmacol. 1989; 13: 673
  • 19 Ozden S, Ozden T, Gumus F, Akin S. Ankara Universitesi Eczacilik Fakultesi Dergisi 1985; 15: 79 ; Chem. Abstr. 1988, 108, 112330
  • 20 Seregin IV, Gevorgyan V. Chem. Soc. Rev. 2007; 36: 1173
    • 21a Wu Y, Li B, Mao F, Li X, Kwong FY. Org. Lett. 2011; 12: 3258
    • 21b Seki M, Nagahama M. J. Org. Chem. 2011; 76: 10198
    • 21c Wang G.-W, Yuan T.-T, Wu X.-L. J. Org. Chem. 2008; 73: 4717
    • 21d Li W, Yin Z, Jiang X, Sun P. J. Org. Chem. 2011; 76: 8543
    • 21e Lyons TW, Hull KL, Sanford MS. J. Am. Chem. Soc. 2011; 133: 4455
    • 21f Caron L, Campeau L.-C, Fagnou K. Org. Lett. 2008; 10: 4533
    • 22a Byun Y.-S, Jung C.-H, Park Y.-T. J. Heterocycl. Chem. 1995; 32: 1835
    • 22b Allin SM, Bowman WR, Elsegood MR. J, McKee V, Karim R, Rahman SS. Tetrahedron 2005; 61: 2689
    • 22c Clyne MA, Aldabbagh F. Org. Biomol. Chem. 2006; 4: 268
    • 22d Bilodeau F, Brochu M.-C, Guimond N, Thesen KH, Forgione P. J. Org. Chem. 2010; 75: 1550
    • 22e Lage S, Martinez-Estibalez U, Sotomayor N, Lete E. Adv. Synth. Catal. 2009; 351: 2460
    • 22f Kozikowski AP, Ma D. Tetrahedron Lett. 1991; 32: 3317
    • 22g Desarbre E, Merour J.-Y. Heterocycles 1995; 41: 1987
    • 22h Campeau L.-C, Parisien M, Jean A, Fagnou K. J. Am. Chem. Soc. 2006; 128: 581
    • 23a Blaszykowski C, Aktoudianakis E, Alberico D, Bressy C, Hulcoop DG, Jafarpour F, Laleu B, Lautens M. J. Org. Chem. 2008; 73: 1888
    • 23b Laha JK, Cuny GD. J. Org. Chem. 2011; 76: 8477
    • 23c Kozikowski AP, Ma D. Tetrahedron Lett. 1991; 32: 3317
    • 23d Kuroda T, Suzuki F. Tetrahedron Lett. 1991; 47: 6915
    • 23e Blaszykowski C, Aktoudianakis E, Bressy C, Alberico D, Lautens M. Org. Lett. 2006; 8: 2043
    • 24a Čerňa I, Pohl R, Hocek M. Chem. Commun. 2007; 4729
    • 24b Čerňa I, Pohl R, Klepetářová B, Hocek M. Org. Lett. 2006; 8: 5389
    • 24c Čerňa I, Pohl R, Klepetářová B, Hocek M. J. Org. Chem. 2008; 73: 9048
    • 25a Storr TE, Baumann CG, Thatcher RJ, De Ornellas S, Whitwood AC, Fairlamb IJ. S. J. Org. Chem. 2009; 74: 5810
    • 25b Storr TE, Strohmeier JA, Baumann CG, Fairlamb IJ. S. Chem. Commun. 2010; 46: 6470
    • 25c Vankova B, Krchnak V, Soural M, Hlavac J. ACS Comb. Sci. 2011; 13: 496
    • 25d Meng G, Niu H.-Y, Qu G.-R, Fossey JS, Li J-P, Guo H-M. Chem. Commun. 2012; 48: 9601
  • 26 Iaroshenko VO, Ostrovskyi D, Milyutina M, Maalik A, Villinger A, Tolmachev A, Volochnyuk DM, Langer P. Adv. Synth. Catal. 2012; 2495
  • 27 General Procedure for the Synthesis of Compounds 6a-n Using Cu and Pd Catalyst: DMF (8 mL) was added to an argon-purged pressure tube containing 3H-imidazo[4,5-b]pyridine 5ah (1 mmol), Pd(OAc)2 (0.05 mmol, 5 mol%), CuI (3 mmol), ArX (2 mmol), and Cs2CO3 (2.5 mmol). The reaction mixture was stirred at 150 °C for 30–60 h. After cooling to r.t., the solvent was evaporated under reduced pressure and the products were isolated and purified by column chromatography (gradient elution n-heptane–EtOAc, EtOAc–i-PrOH)
  • 28 3-Phenethyl-2-phenyl-5-(thiophen-2-yl)-7-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (6i): Bright-yellow solid; mp 137–139 °C; 1H NMR (300.13 MHz, CDCl3): δ = 3.14 (t, J = 6.99, 2 H, CH2), 4.57 (t, J = 7.55, 2 H, CH2), 6.99 (d, J = 8.12 Hz, 2 H, ArH), 7.12–7.16 (m, 2 H, ArH), 7.28–7.44 (m, 5 H, ArH), 7.51–7.59 (m, 2 H, ArH), 7.63 (d, J = 7.18 Hz, 2 H, ArH), 7.76 (s, 1 H, ArH); 13C NMR (62.89 MHz, CDCl3): δ = 35.6 (CH2), 45.6 (CH2), 110.3 (q, 3 J C–F = 4.12 Hz, CH), 122.8 (q, 1 J C–F = 274.00 Hz, CF3), 124.2 (CH), 125.8 (2CH), 126.0 (CH), 126.9 (CH), 127.9 (CH), 128.3 (q, 2 J C–F = 33.88 Hz, C), 128.7 (CH), 128.8 (3CH), 129.0 (CH), 129.3 (CH), 129.5 (C), 130.4 (CH), 134.2 (C), 137.4 (C), 143.4 (C), 146.6 (C), 149.8 (C), 156.5 (C); 19F NMR (282.40 MHz, CDCl3): δ = –61.99 (ArCF3); IR (ATR): 3025 (w), 2960 (s), 2927 (m), 2868 (w), 1907 (w), 1732 (w), 1600 (m), 1544 (m), 1496 (m), 1467 (w), 1453 (w), 1443 (w), 1418 (w), 1384 (s), 1367 (w), 1339 (w), 1329 (w), 1309 (w), 1271 (m), 1250 (m), 1228 (w), 1155 (w), 1125 (s), 1099 (w), 1073 (w), 1049 (w), 1029 (w), 1020 (w), 1004 (w), 959 (w), 942 (w), 929 (w), 898 (w), 868 (m), 846 (w), 833 (w), 809 (s), 779 (w), 755 (m), 739 (w), 696 (w), 684 (m), 666 (w), 618 (w), 609 (w), 586 (w), 558 (m), 532 (w) cm–1; GC-MS (EI, 70 eV): m/z (%) = 449 (26) [M]+, 358 (2), 345 (100), 324 (1), 242 (1), 208 (2), 186 (1), 146 (1), 105 (1), 91 (1), 77 (2); HRMS (ESI): m/z [M + H]+ calcd for C25H19F3N3S: 450.12463; found: 450.12452
    • 29a Guihaumé J, Halbert S, Eisenstein O, Perutz RN. Organometallics 2012; 31: 1300
    • 29b Clot E, Eisenstein O, Jasim N, Macgregor SA, McGrady JE, Perutz RN. Acc. Chem. Res. 2011; 44: 333
    • 29c Xin P.-Y, Niu H.-Y, Qu G.-R, Ding R.-F, Guo H.-M. Chem. Commun. 2012; 48: 6717
  • 30 General Procedure for the Synthesis of Compounds 6a–n Using Ni Catalyst: DMF (8 mL) was added to an argon-purged pressure tube containing 3H-imidazo[4,5-b]pyridine 5ah (1 mmol), [NiCl2(PPh3)2] (0.05 mmol, 5 mol%), ArX (2 mmol), and K2CO3 (2.5 mmol). The reaction mixture was stirred at 110 °C for 15 h. After cooling to r.t., the solvent was evaporated under reduced pressure and the products were isolated and purified by column chromatography (gradient elution n-heptane–EtOAc, EtOAc–i-PrOH)
  • 31 Hegedus LS In Organometallics in Synthesis . Schlosser M. John Wiley and Sons; Chichester: 2002: 1123-1217
  • 32 Pintori DG, Greaney MF. J. Am. Chem. Soc. 2011; 133: 1209
  • 33 Huang J, Chan J, Chen Y, Borths CJ, Baucom KD, Larsen RD, Faul MM. J. Am. Chem. Soc. 2010; 132: 3674
    • 34a Schareina T, Zapf A, Mägerlein W, Müller N, Beller M. Synlett 2007; 555
    • 34b Schareina T, Zapf A, Mägerlein W, Müller N, Beller M. Chem.–Eur. J. 2007; 13: 6249