Palladium-Catalyzed Oxidative Annulation of Pyrrolylalkyl-1H-azoles: Towards the Synthesis of Polyheterocyclic Arenes

Abstract

A highly efficient and regioselective palladium-catalyzed annulation protocol for a series of linear and terminally substituted 1,2- and 1,3-di(heteroaryl)alkanes to the corresponding polyheterocyclic arenes is reported. Herein, intramolecular oxidative coupling involving double C(sp²)–H bond functionalization provides a feasible access to biheteroaryl systems annulated to a six-membered ring. The methodology is not restricted to six-membered annulations and was extended to the synthesis of compounds with a seven-membered ring and biheteroaryl core.

Key words

C–H functionalization - pyrroles - oxidative coupling - palladium - imidazoles

• References

• 1a Kong W.-J, Chen X, Wang M, Dai H.-X, Yu J.-Q. Org. Lett. 2018; 20: 284
• 1b Gvozdev VD, Shavrin KN, Baskir EG, Egorov MP, Nefedov OM. Russ. Chem. Bull. 2016; 65: 1829
• 1c Jacobi PA, Lee K. J. Am. Chem. Soc. 2000; 122: 4295
• 2a Santora VJ, Almos TA, Barido R, Basinger J, Bellows CL, Bookser BC, Breitenbucher JG, Broadbent NJ, Cabebe C, Chai C.-K, Chen M, Chow S, Chung DM, Crickard L, Danks AM, Freestone GC, Gitnick D, Gupta V, Hoffmaster C, Hudson AR, Kaplan AP, Kennedy MR, Lee D, Limberis J, Ly K, Mak CC, Masatsugu B, Morse AC, Na J, Neul D, Nikpur J, Peters M, Petroski RE, Renick J, Sebring K, Sevidal S, Tabatabaei A, Wen J, Yan Y, Yoder ZW, Zook D. J. Med. Chem. 2018; 61: 6018
• 2b Asproni B, Manca I, Pinna G, Cichero E, Fossa P, Murineddu G, Lazzari P, Loriga G, Pinna GA. Chem. Biol. Drug Des. 2018; 91: 181
• 2c Tenora L, Galeta J, Renzickova E, Krystof V, Potacek M. J. Org. Chem. 2016; 81: 11841
• 2d Bai X.-G, Yu D.-K, Wang J.-X, Zhang H, He H.-W, Shao R.-G, Li X.-M, Wang Y.-C. Bioorg. Med. Chem. Lett. 2012; 22: 6947
• 2e Caruso M, Beria I, Brasca MG, Ferguson R, Posteri H. PCT Int. Appl WO2008043745, 2008
• 3a Sobenina LN, Sagitova EF, Ushakov IA, Trofimov BA. Synthesis 2017; 49: 4065 ; and references cited therein
• 3b Piltan M, Moradi L, Abasi G, Zarei SA. Beilstein J. Org. Chem. 2013; 9: 510
• 4a Meta E, Brullo C, Tonelli M, Franzblau SG, Wang Y, Ma R, Baojie W, Orena BS, Pasca MR, Bruno O. Med. Chem. 2019; 15: 17
• 4b Vicentini CB, Veronese AC, Giori P, Lumachi B, Guarneri M. Tetrahedron 1990; 46: 5777
• 5a Argiriadi M, Breinlinger E, Dietrich JD, Friedman M, Ihle D, Morytko M, Mullen K, Osuma A, Schiavo GY. L, Wilson NS. WO2016168633A1, 2016
• 5b Satyanarayana Y, Lown JW. Heterocycl. Commun. 2000; 6: 199
• 6 Forster M, Chaikuad A, Dimitrov T, Döring E, Holstein J, Berger B.-T, Gehringer M, Ghoreschi K, Müller S, Knapp S, Laufer SA. J. Med. Chem. 2018; 61: 5350
• 7a Varasi M, Heidempergher F, Caccia C, Salvati P. PCT Int. Appl WO1995032209, 1995 ; Chem. Abstr. 1996, 124, 232456
• 7b Yamawaki I, Matsushita Y, Asaka N, Ohmori K, Nomura N, Ogawa K. Eur. J. Med. Chem. 1993; 28: 481
• 8 Paeshuyse J, Chezal J.-M, Froeyen M, Leyssen P, Dutartre H, Vrancken R, Canard B, Letellier C, Li T, Mittendorfer H, Koenen F, Kerkhofs P, De Clercq E, Herdewijn P, Puerstinger G, Gueiffier A, Chavignon O, Teulade J.-C, Neyts J. J. Virol. 2007; 81: 11046
• 9a Likhosherstov AM, Filippova OV, Peresada VP, Kryzhanovskii SA, Vititnova MB, Kaverina NV, Reznikov KM. Pharm. Chem. J. 2003; 37: 6
• 9b Negoro T, Murata M, Ueda S, Fujitani B, Ono Y, Kuromiya A, Komiya M, Suzuki K, Matsumoto J.-i. J. Med. Chem. 1998; 41: 4118
• 9c Seredenin SB, Voronina TA, Beshimov A, Peresada VP, Likhosherstov AM. RU Patent 2099055, 1997
• 9d Seredenin SB, Voronina TA, Likhosherstov AM, Peresada VP, Molodavkin GM, Halikas JA. US Patent 5378846, 1995
• 9e Peresada VP, Medvedev OS, Likhosherstov AM, Skoldinov AP. Khim.-Farm. Zh. 1987; 21: 1054
• 10a Lei A, Shi W, Liu C, Liu W, Zhang H, He C. Oxidative Cross-Coupling Reactions . Wiley-VCH; Weinheim: 2017
• 10b Laha JK, Jethava KP, Dayal N. J. Org. Chem. 2014; 79: 8010 ; and references cited therein
• 10c Liu C, Zhang H, Shi W, Lei A. Chem. Rev. 2011; 111: 1780
• 11a Baumann M, Baxendale IR. Beilstein J. Org. Chem. 2013; 9: 2265
• 11b Kotschy A, Timári G. Heterocycles from Transition Metal Catalysis: Formation and Functionalization. Catalysis by Metal Complexes, Vol. 28. Springer; Dordrecht: 2005. Chap. 4, 69
• 12a Wang GW, Yuan TT, Li DD. Angew. Chem. Int. Ed. 2011; 50: 1380
• 12b Ishida N, Nakanishi Y, Moriya T, Murakami M. Chem. Lett. 2011; 40: 1047
• 12c Borduas N, Lough AJ, Dong VM. Inorg. Chim. Acta 2011; 369: 247
• 12d Yeung CS, Zhao X, Borduas N, Dong VM. Chem. Sci. 2010; 1: 331
• 13 Yoshikai N, Wei Y. Asian J. Org. Chem. 2013; 2: 466
• 14a Kandukuri SR, Oestreich M. J. Org. Chem. 2012; 77: 8750
• 14b Pintori DG, Greaney MF. J. Am. Chem. Soc. 2011; 133: 1209
• 14c Ackermann L, Jeyachandran R, Potukuchi HK, Novák P, Büttner L. Org. Lett. 2010; 12: 2056
• 14d Liégault B, Fagnou K. Organometallics 2008; 27: 4841
• 14e Ackermann L, Vicente R, Althammer A. Org. Lett. 2008; 10: 2299
• 14f Dwight TA, Rue NR, Charyk D, Josselyn R, Boef BD. Org. Lett. 2007; 9: 3137
• 15a Gupta V, Rao VU. B, Das T, Vanka K, Singh RP. J. Org. Chem. 2016; 81: 5663
• 15b Gupta V, Pandey SK, Singh RP. Org. Biomol. Chem. 2018; 16: 7134
• 15c Liégault B, Lee D, Huestis MP, Stuart DR, Fagnou K. J. Org. Chem. 2008; 73: 5022
• 16a Mínguez JM, Castellote MI, Vaquero JJ, García-Navio JL, Alvarez-Builla J, Castaño O, Andrés JL. J. Org. Chem. 1996; 61: 4655
• 16b Tsizorik NM, Hrynyshyn YV, Bol’but AV, Vovk MV. Chem. Heterocycl. Compd. 2018; 54: 1075
• 16c Ramesh S, Kr Ghosh S, Nagarajan R. Org. Biomol. Chem. 2013; 11: 7712
• 17 He Y, Lin M, Li Z, Liang X, Li G, Antilla GC. Org. Lett. 2011; 13: 4490
• 18 Beccalli EM, Broggini G, Martinelli M, Paladino G. Tetrahedron 2005; 61: 1077
• 19 Basceken S, Balci M. J. Org. Chem. 2015; 80: 3806
• 20a Tripathi KN, Ray D, Singh RP. Org. Biomol. Chem. 2017; 15: 10082
• 20b Tripathi KN, Ray D, Singh RP. Eur. J. Org. Chem. 2017; 5809
• 20c Ray D, Manikandan T, Roy A, Tripathi KN, Singh RP. Chem. Commun. 2015; 51: 7065
• 21 CCDC 1918664 (2a) 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.