Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of 2-Alkynylquinoline-3-carbaldehydes: Access to (Hetero)arylpyranoquinolines

Abstract

A silver trifluoromethanesulfonate catalyzed efficient access to the indolylpyranoquinoline scaffold is reported. Starting from 2-alkynylquinoline-3-carbaldehyde units with various substitution patterns on the quinoline and alkynyl parts, the use of silver trifluoromethanesulfonate (10 mol%) in 1,2-dichloroethane allowed a domino hydroarylation/cycloisomerization reaction, generating (hetero)aryl-functionalized pyranoquinolines. The heteroarenes that were used are N-methylindole (18 compounds, 67–100%), indole, and 2-methylindole (4 compounds, 36–89%), and the reaction was also compatible to a lesser extent with arenes such as pyrroles (5 compounds, 43–90%), 1,3,5-trimethoxybenzene, and 3-methylbenzofuran.

Key words - hydroarylation - silver - cycloisomerization - indolylpyranoquinolines - domino reaction - cyclofunctionalization

• References

• 1a Zhang M.-Z, Chen Q, Yang G.-F. Eur. J. Med. Chem. 2015; 89: 421
• 1b Sharma V, Kumar P, Pathak D. J. Heterocycl. Chem. 2010; 47: 491
• 1c Kaushik NK, Kaushik N, Attri P, Kumar N, Kim CH, Verma AK, Choi EH. Molecules 2013; 18: 6620
• 1d Michael JP. Nat. Prod. Rep. 2007; 24: 223
• 1e Abdel-Wahab BF, Khidre RE, Farahat A.-AS, El-Ahl A.-A. ARKIVOC 2012; (i): 211
• 1f Mukherjee S, Pal M. Curr. Med. Chem. 2013; 20: 4386
• 1g Pati B, Banerjee S. J. PharmaSciTech 2014; 3: 59
• 1h Kumar S, Bawa S, Gupta H. Mini-Rev. Med. Chem. 2009; 9: 1648
• 2a Burke MD, Schreiber SL. Angew. Chem. Int. Ed. 2004; 43: 46
• 2b Diversity-Oriented Synthesis: Basics and Applications in Organic Synthesis, Drug Discovery, and Chemical Biology. Trabocchi A. Wiley; New York: 2013
• 3a Maguire MP, Sheets KR, McVety K, Spada AP, Zilbersteint A. J. Med. Chem. 1994; 37: 2129
• 3b Oliva B, Miller K, Caggiano N, O’Neill AJ, Cuny GD, Hoemann MZ, Hauske JR, Chopra I. Antimicrob. Agents Chemother. 2003; 47: 458
• 3c Kuethe JT, Wong A, Qu C, Smitrovich J, Davies IW, Hughes DL. J. Org. Chem. 2005; 70: 2555
• 3d Payack JF, Vazquez E, Matty L, Kress MH, McNamara JA. J. Org. Chem. 2005; 70: 175
• 3e Bhowal SK, Lala S, Hazra A, Paira P, Banerjee S, Mondal NB, Chakraborty S. Contraception 2008; 77: 214
• 3f Liu CY, Wu PT, Wang JP, Fan PW, Hsieh CH, Su CL, Chiu CC, Yao CF, Fang K. Apoptosis 2015; 20: 1471
• 4a Chao C.-M, Beltrami D, Toullec PY, Michelet V. Chem. Commun. 2009; 6988
• 4b Pradal A, Chao C.-M, Beltrami D, Toullec PY, Michelet V. Beilstein J. Org. Chem. 2011; 7: 1021
• 4c Pradal A, Chen Q, Faudot dit Bel P, Toullec PY, Michelet V. Synlett 2012; 23: 74
• 4d Chao C.-M, Toullec PY, Michelet V. Tetrahedron Lett. 2009; 50: 3719
• 4e Toullec PY, Blarre T, Michelet V. Org. Lett. 2009; 11: 2888
• 4f Chao C.-M, Vitale MR, Toullec PY, Genêt J.-P, Michelet V. Chem. Eur. J. 2009; 15: 1319
• 4g Leseurre L, Toullec PY, Genêt J.-P, Michelet V. Org. Lett. 2007; 9: 4049
• 5a Arcadi A, Chiarini M, Del Vecchio L, Marinelli F, Michelet V. Chem. Commun. 2016; 52: 1458
• 5b Arcadi A, Pietropaolo E, Alvino A, Michelet V. Org. Lett. 2013; 15: 2766
• 6a Carrër A, Péan C, Perron-Sierra F, Mirguet O, Michelet V. Adv. Synth. Catal. 2016; 358: 1540
• 6b Belmont P, Andrez J.-C, Allan CS. M. Tetrahedron Lett. 2004; 45: 2783
• 6c Godet T, Belmont P. Synlett 2008; 2513
• 7a Tiano M, Belmont P. J. Org. Chem. 2008; 73: 4101
• 7b Belmont P, Belhadj T. Org. Lett. 2005; 7: 1793
• 8a Godet T, Vaxelaire C, Michel C, Milet A, Belmont P. Chem. Eur. J. 2007; 13: 5632
• 8b Michel C, Godet T, Dheu-Andries M.-L, Belmont P, Milet A. J. Mol. Struct. 2007; 811: 175
• 8c Belmont P, Parker E. Eur. J. Org. Chem. 2009; 6075
• 8d Parker E, Leconte N, Godet T, Belmont P. Chem. Commun. 2011; 47: 343
• 8e Bantreil X, Vaxelaire C, Godet T, Parker E, Sauer C, Belmont P. Org. Biomol. Chem. 2011; 9: 4831
• 8f Belmont P In Silver in Organic Chemistry . Harmata M. Wiley; Hoboken: 2010
• 9a Dell’Acqua M, Facoetti D, Abbiati G, Rossi E. Synthesis 2010; 2367
• 9b Dell’Acqua M, Castano B, Cecchini C, Pedrazzini T, Pirovano V, Rossi E, Caselli A, Abbiati G. J. Org. Chem. 2014; 79: 3494
• 9c Kotera A, Uenishi JI, Uemura M. Tetrahedron Lett. 2010; 51: 1166
• 9d Liu L.-P, Hammond GB. Org. Lett. 2010; 12: 4640
• 9e Bacchi A, Costa M, Della Ca’ N, Fabbricatore M, Fazio A, Gabriele B, Nasi C, Salerno G. Eur. J. Org. Chem. 2004; 574
• 9f Obika S, Kono H, Yasui Y, Yanada R, Takemoto Y. J. Org. Chem. 2007; 72: 4462
• 9g Asao N, Nogami T, Takahashi K, Yamamoto Y. J. Am. Chem. Soc. 2002; 124: 764
• 9h Patil NT, Yamamoto Y. J. Org. Chem. 2004; 69: 5139
• 9i Mondal S, Nogami T, Asao N, Yamamoto Y. J. Org. Chem. 2003; 68: 9496
• 9j Wei L.-L, Wei L.-M, Pan W.-B, Wu M.-J. Synlett 2004; 1497
• 9k Gulias M, Rodriguez JR, Castedo L, Mascareñas JL. Org. Lett. 2003; 5: 1975
• 9l Jha RR, Aggarwal T, Verma AK. Tetrahedron Lett. 2014; 55: 2603
• 9m For an enantioselective version, see: Handa S, Slaughter LM. Angew. Chem. Int. Ed. 2012; 51: 2912
• 9n Nanayakkara YS, Woods RM, Breitbach ZS, Handa S, Slaughter LM, Armstrong DW. J. Chromatogr. A 2013; 1305, 94

For selected work using nonmetallic electrophiles or non-transition metals, see:
• 9o Barluenga J, Vazquez-Villa H, Ballesteros A, Gonzalez JM. J. Am. Chem. Soc. 2003; 125: 9028
• 9p Yue D, Della Ca N, Larock RC. Org. Lett. 2004; 6: 1581
• 9q Dell’Acqua M, Facoetti D, Abbiati G, Rossi E, Alfonsi M, Arcadi A. Eur. J. Org. Chem. 2009; 2852
• 10 Yao X, Li C.-J. Org. Lett. 2006; 8: 1953
• 11 Yu X, Ding Q, Wang W, Wu J. Tetrahedron Lett. 2008; 49: 4390
• 12 Domaradzki ME, Long Y, She Z, Liu X, Zhang G, Chen Y. J. Org. Chem. 2015; 80: 11360
• 13a Beeler AB, Su S, Singleton CA, Porco JA. Jr. J. Am. Chem. Soc. 2007; 129: 1413
• 13b Leng B, Chichetti S, Su S, Beeler AB, Porco JA. Jr. Beilstein J. Org. Chem. 2012; 8: 1338
• 14a Asao N, Chan CS, Takahashi K, Yamamoto Y. Tetrahedron 2005; 61: 11322
• 14b Bhunia S, Wang K.-C, Liu R.-S. Angew. Chem. Int. Ed. 2008; 47: 5063
• 15 Tomas-Mendivil E, Starck J, Ortuno J.-C, Michelet V. Org. Lett. 2015; 17: 6126
• 16a Dyker G, Hildebrandt D, Liu J, Merz K. Angew. Chem. Int. Ed. 2003; 42: 4399
• 16b Tang R.-Y, Li J.-H. Chem. Eur. J. 2010; 16: 4733
• 16c Ouyang B, Yuan J, Yang Q, Ding Q, Peng Y, Wu J. Heterocycles 2011; 82: 1239
• 16d Mariaule G, Newsome G, Toullec PY, Belmont P, Michelet V. Org. Lett. 2014; 16: 4570
• 17 Meth-Cohn O, Narine B, Tarnowski B. J. Chem. Soc., Perkin Trans. 1 1981; 1520
• 18 Meth-Cohn O, Narine B, Tarnowski B, Hayes R, Keyzad A, Rhouati S, Robinson A. J. Chem. Soc., Perkin Trans. 1 1981; 2509
• 19 Mayr H. Tetrahedron 2015; 71: 5095