Synthesis 2018; 50(17): 3513-3519
DOI: 10.1055/s-0037-1610071
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed C–N Bond Formation via C–H Functionalization: Facile Synthesis of Multisubstituted Imidazo[1,2-a]pyridines from N-(2-Pyridinyl)enaminones

Sandro Cacchi
a   Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy   Email: antonia.iazzetti@uniroma1.it
,
Alessia Ciogli
a   Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy   Email: antonia.iazzetti@uniroma1.it
,
Nicola Demitri
b   Elettra-Sincrotrone Trieste, S.S. 14 Km 163.5 in Area Science Park, 34149 Basovizza, Trieste, Italy
,
Giancarlo Fabrizi
a   Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy   Email: antonia.iazzetti@uniroma1.it
,
Francesca Ghirga
c   Center for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia, Viale Regina Elena 291, 00161 Rome, Italy
,
Antonella Goggiamani
a   Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy   Email: antonia.iazzetti@uniroma1.it
,
Antonia Iazzetti*
a   Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy   Email: antonia.iazzetti@uniroma1.it
,
Doriano Lamba
d   Istituto di Cristallografia–CNR, S.S. 14 Km 163.5 in Area Science Park, 34149 Basovizza, Trieste, Italy
› Author Affiliations
Further Information

Publication History

Received: 01 March 2018

Accepted after revision: 03 May 2018

Publication Date:
28 June 2018 (online)


Abstract

An efficient, new copper-catalyzed approach to the construction of the multisubstituted imidazo[1,2-a]pyridine skeleton from N-(2-pyridinyl)enaminones has been developed.

Supporting Information

 
  • References


    • For selected reviews, see:
    • 1a Stanovnik B. Svete J. Chem. Rev. 2004; 104: 2433
    • 1b Svete J. Monatsh. Chem. 2004; 135: 629
    • 1c Negri G. Kascheres C. Kascheres AJ. J. Heterocycl. Chem. 2004; 41: 461
    • 1d Svete J. ARKIVOC 2006; (vii): 35
    • 1e Palmieri G. Cimarelli C. ARKIVOC 2006; (vi): 104
    • 1f Simunek P. Machacek V. Dyes Pigm. 2010; 86: 197
    • 1g Shawali AS. ARKIVOC 2012; (i): 383

      For selected references, see:
    • 2a Zhang R. Zhang D. Guo Y. Zhou G. Jian Z. Dong D. J. Org. Chem. 2008; 73: 9504
    • 2b Ban X. Pan Y. Lin Y. Wang S. Du Y. Zhao K. Org. Biomol. Chem. 2012; 10: 3606
    • 2c Edwankar RV. Edwankar CR. Namjoshi OA. Deschamps JR. Cook JM. J. Nat. Prod. 2012; 75: 181
    • 2d Shao Y. Zhu K. Qin Z. Li E. Li Y. J. Org. Chem. 2013; 78: 5731
    • 2e Labarrios E. Jerezano A. Jimenez F. del Carmen Cruz M. Delgado F. Zepeda LG. Tamariz J. J. Heterocycl. Chem. 2014; 51: 954
    • 2f Yan R. Li X. Yang X. Kang X. Xiang L. Huang G. Chem. Commun. 2015; 51: 2573

      Selected references; for Pd-catalyzed reactions, see:
    • 3a Sorensen US. Pombo-Villar E. Helv. Chim. Acta 2004; 87: 82
    • 3b Wuertz S. Rakshit S. Neumann JJ. Droege T. Glorius F. Angew. Chem. Int. Ed. 2008; 47: 7230
    • 3c Weng B. Liu R. Li J.-H. Synthesis 2010; 2926
    • 3d Bautista R. Montoya PA. Rebollar A. Burgueño E. Tamariz J. Molecules 2013; 18: 10334
    • 3e Gu Z.-Y. Zhu T.-H. Cao J.-J. Xu X.-P. Wang S.-Y. Ji S.-J. ACS Catal. 2014; 4: 49

    • For Cu-catalyzed reactions, see:
    • 3f Guengoer FS. Anac O. Sezer O. Tetrahedron Lett. 2007; 48: 4883
    • 3g Yan S. Wu H. Wu N. Jiang Y. Synlett 2007; 2699
    • 3h Liu J. Zhang X. Peng H. Jiang H. Yin B. Adv. Synth. Catal. 2015; 357: 727

    • For Au-catalyzed reactions, see:
    • 3i Saito A. Konishi T. Hanzawa Y. Org. Lett. 2010; 12: 372
    • 3j Goutham K. Mangina NS. V. M. R. Suresh S. Raghavaiah P. Karunakar GV. Org. Biomol. Chem. 2014; 12: 2869

    • For Ag-catalyzed reactions, see:
    • 3k Robinson RS. Dovey MC. Gravestock D. Tetrahedron Lett. 2004; 45: 6787
    • 3l Martins MA. P. Rossatto M. Frizzo CP. Scapin E. Buriol L. Zanatta N. Bonacorso HG. Tetrahedron Lett. 2013; 54: 847
    • 5a Enguehard-Gueiffier C. Gueiffier A. Mini-Rev. Med. Chem. 2007; 7: 888
    • 5b Chernyak N. Gevorgyan V. Angew. Chem. Int. Ed. 2010; 49: 2743 ; and references cited therein
    • 5c Deep A. Bhatia RK. Kaur R. Kumar S. Jain UK. Singh H. Batra S. Kaushik D. Deb KP. Curr. Top. Med. Chem. 2017; 17: 238
    • 6a Swainston Harrison T. Keating GM. CNS Drugs 2005; 19: 65
    • 6b Hsua N. Jha SK. Coleman T. Frank MG. Behav. Brain Res. 2009; 201: 233
  • 7 Almirante L. Polo L. Mugnaini A. Provinciali E. Rugarli P. Biancotti A. Gamba A. Murmann W. J. Med. Chem. 1965; 8: 305
    • 8a Langer SZ. Arbilla S. Benavides J. Scatton B. Adv. Biochem. Psychopharmacol. 1990; 46: 6
    • 8b Berson A. Descatoire V. Sutton A. Fau D. Maulny B. Vadrot N. Feldmann G. Berthon B. Tordjmann T. Pessayre D. J. Pharmacol. Exp. Ther. 2001; 299: 793
    • 8c Okubo T. Yoshikawa R. Chaki S. Okuyamac S. Nakazato A. Bioorg. Med. Chem. 2004; 12: 423
    • 8d Jain AN. J. Med. Chem. 2004; 47: 947
  • 9 Uemura Y. Tanaka S. Ida S. Yuzuriha T. J. Pharm. Pharmacol. 1993; 45: 1077
  • 10 Gudmundsson K. Boggs SD. PCT Int. Appl WO 2006026703, 2006 ; Chem. Abstr. 2006, 144, 274.

    • For recent reviews, see:
    • 11a Koubachi J. El Kazzouli S. Bousmina M. Guillaumet G. Eur. J. Org. Chem. 2014; 5119
    • 11b Pericherla K. Kaswan P. Pandey K. Kumar A. Synthesis 2015; 47: 887
    • 11c Bagdi AK. Santra S. Monir K. Hajra A. Chem. Commun. 2015; 51: 1555
    • 11d Selvaraj MR. Patil SM. Palaniraja J. Res. Chem. Intermed. 2016; 42: 2749

    • See also:
    • 11e 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
    • 11f Adib M. Mahdavi M. Noghani MA. Mirxaei P. Tetrahedron Lett. 2007; 48: 7263
    • 11g 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
    • 11h 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
    • 11i Parenty AD. C. Cronin L. Synthesis 2008; 1479
    • 11j Denora N. Laquintana V. Pisu MG. Dore R. Murru L. Latrofa A. Trapani G. Sanna E. J. Med. Chem. 2008; 51: 6876
    • 11k Koubachi J. Berteina-Raboin S. Mouaddib A. Guillaumet G. Synthesis 2009; 271
    • 11l Zeng J. Tan YJ. Leow ML. Liu X.-W. Org. Lett. 2012; 14: 4386
    • 11m Monir K. Bagdi AK. Mishra S. Majee A. Hajra A. Adv. Synth. Catal. 2014; 356: 1105
  • 12 Karpov AS. Müller TJ. Org. Lett. 2003; 5: 3451
  • 13 Sakamoto T. Nagano T. Kondo Y. Yamanaka H. Synthesis 1990; 215
    • 14a The structure of 2a, and that of all the other cyclization products, was indirectly confirmed by an X-ray crystal structure analysis of 2m. CCDC 1819911 (2m) 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.