RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2018; 50(17): 3513-3519
DOI: 10.1055/s-0037-1610071
DOI: 10.1055/s-0037-1610071
paper
Copper-Catalyzed C–N Bond Formation via C–H Functionalization: Facile Synthesis of Multisubstituted Imidazo[1,2-a]pyridines from N-(2-Pyridinyl)enaminones
Weitere Informationen
Publikationsverlauf
Received: 01. März 2018
Accepted after revision: 03. Mai 2018
Publikationsdatum:
28. Juni 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.
Key words
copper - enaminones - imidazo[1,2-a]pyridines - cyclization - C–N bond formation - C–H functionalizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610071.
- Supporting Information
-
References
- 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
- 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
- 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
- 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
- 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
- 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
- 4a Cacchi S. Fabrizi G. Filisti E. Org. Lett. 2008; 10: 2629
- 4b Bernini R. Cacchi S. Fabrizi G. Filisti E. Sferrazza A. Synlett 2009; 1480
- 4c Bernini R. Cacchi S. Fabrizi G. Sferrazza A. Synthesis 2009; 1209
- 4d Bernini R. Fabrizi G. Sferrazza A. Cacchi S. Angew. Chem. Int. Ed. 2009; 48: 8078
- 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.
- 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
- 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.
For selected reviews, see:
For selected references, see:
Selected references; for Pd-catalyzed reactions, see:
For Cu-catalyzed reactions, see:
For Au-catalyzed reactions, see:
For Ag-catalyzed reactions, see:
For recent reviews, see:
See also: