Synthesis 2015; 47(09): 1337-1347
DOI: 10.1055/s-0034-1379894
paper
© Georg Thieme Verlag Stuttgart · New York

Diversely Substituted Indoloazepinones and Indoloazocinones: A Post-Ugi Gold-Catalyzed Regioselective Carbocyclization Approach

Dipak D. Vachhani
a  Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001 Leuven, Belgium
,
Amit Kumar
a  Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001 Leuven, Belgium
b  Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India   Email: [email protected]
,
Sachin G. Modha*
a  Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001 Leuven, Belgium
,
Sunil K. Sharma
b  Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India   Email: [email protected]
,
Virinder S. Parmar
b  Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India   Email: [email protected]
,
Erik V. Van der Eycken*
a  Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001 Leuven, Belgium
› Author Affiliations
Further Information

Publication History

Received: 27 October 2014

Accepted after revision: 15 January 2015

Publication Date:
26 February 2015 (online)


Abstract

A post-Ugi gold-catalyzed regioselective intramolecular carbocyclization strategy is reported. A better cationic gold system, compared to our previous report, has been optimized and utilized. The method presented exhibits excellent functional group compatibility including bulky substitutions on alkynes and allows the direct access to indoloazepinones and indoloazocinones in good to excellent yields.

Supporting Information

 
  • References

  • 1 Present address: Chemistry Building-4.20b, School of Chemistry, The University of Manchester, Manchester M13 9PL, UK.
  • 2 Newman DJ, Cragg GM, Snader KM. J. Nat. Prod. 2003; 66: 1022
    • 3a Magolan J, Kerr MA. Org. Lett. 2006; 8: 4561
    • 3b Kam T.-S, Sim K.-M, Lim T.-M. Tetrahedron Lett. 2000; 41: 2733
    • 4a Sausville EA, Zaharevitz D, Gussio R, Meijer L, Louran-Leost M, Kunick C, Schultz R, Lahusen T, Headlee D, Stinson S, Arbuck SG, Senderowicz A. Pharmacol. Ther. 1999; 82: 285
    • 4b Zaharevitz DZ, Gussio R, Leost M, Senderowicz A, Lahusen T, Kunick C, Meijer L, Sausville EA. Cancer Res. 1999; 59: 2566
    • 5a Irlinger B, Bartsch A, Kramer H.-J, Mayser P, Steglich W. Helv. Chim. Acta 2005; 88: 1472
    • 5b Mayser P, Wenzel M, Kramer H.-J, Kindler BL. J, Spiteller P, Haase G. Med. Mycol. 2007; 45: 519
    • 5c Zuther K, Mayser P, Hettwer U, Wu W, Spiteller P, Kindler BL. J, Karlovsky P, Basse CW, Schirawski J. Mol. Microbiol. 2008; 68: 152
  • 6 Sharma V, Lansdell TA, Jin G, Tepe JJ. J. Med. Chem. 2004; 47: 3700
    • 7a Frank KE, Fu J-m, Acker BA, Ennis MD, Fisher JF, Jacobsen EJ, McWhorter WW, Morris JK, Rogier Jr.; (Upjohn Co.) DJ. Patent WO 02/24700, 2002 ; Chem. Abstr. 2002, 136, 279440p.
    • 7b Frank KE, Fu J-m, Acker BA, Ennis MD, Fisher JF, Jacobsen EJ, McWhorter WW, Morris JK, Rogier Jr.; (Upjohn Co.) DJ. Patent WO 02/24701, 2002 ; Chem. Abstr. 2002, 136, 279356r.
    • 7c Kraxner J, Hubner H, Gmeiner P. Arch. Pharm. Pharm. Med. Chem. 2000; 333: 287
    • 8a Donets PA, Van der Eycken EV. Synthesis 2011; 2147
    • 8b Gruit M, Pews-Davtyan A, Beller M. Org. Biomol. Chem. 2011; 9: 1148
    • 8c Stuart DR, Alsabeh P, Kuhn M, Fagnou K. J. Am. Chem. Soc. 2010; 132: 18326
    • 8d Reyes-Gutiérrez PE, Torres-Ochoa RO, Martínez R, Miranda LD. Org. Biomol. Chem. 2009; 7: 1388
    • 8e Power DP, Lozach O, Meijer L, Grayson DH, Connon SJ. Bioorg. Med. Chem. Lett. 2010; 20: 4940
    • 8f White AW, Carpenter N, Lottin JR. P, McClelland RA, Nicholson RI. Eur. J. Med. Chem. 2012; 56: 246

      For the synthesis of indoloazepines using isonitrile based multicomponent reaction, see:
    • 9a Zhang L, Zheng M, Zhao F, Zhai Y, Liu H. ACS Comb. Sci. 2014; 16: 184
    • 9b Subba Reddy BS, Ganesh AV, Vani M, Murthi TR, Kalivendi SV, Yadav JS. Bioorg. Med. Chem. Lett. 2014; 24: 4501
    • 9c Zhang L, Zhao F, Zheng M, Zhai Y, Liu H. Chem. Commun. 2013; 49: 2894
    • 9d Beaumont S, Retailleau P, Dauban P, Dodd RH. Eur. J. Org. Chem. 2008; 5162
    • 9e Gordillo-Cruz RE, Rentería-Gómez A, Islas-Jácome A, Cortes-García CJ, Díaz-Cervantes E, Robles J, Gámez-Montaño R. Org. Biomol. Chem. 2013; 11: 6470
    • 9f Jida M, Betti C, Urbanczyk-Lipkowska Z, Tourwé D, Ballet S. Org. Lett. 2013; 15: 5866
    • 10a Modha SG, Kumar A, Vachhani DD, Jacobs J, Sharma SK, Parmar VS, Van Meervelt L, Van der Eycken EV. Angew. Chem. Int. Ed. 2012; 51: 9572
    • 10b Modha SG, Kumar A, Vachhani DD, Sharma SK, Parmar VS, Van der Eycken EV. Chem. Commun. 2012; 48: 10916
    • 10c Dyker G. Angew. Chem. Int. Ed. 2000; 39: 4237
    • 10d Hashmi AS. K, Hutchings G. Angew. Chem. Int. Ed. 2006; 45: 7896
    • 10e Hashmi AS. K. Chem. Rev. 2007; 107: 3780
    • 10f Fürstner A, Davies PW. Angew. Chem. Int. Ed. 2007; 46: 3410
    • 10g Gorin DJ, Sherry BD, Toste FD. Chem. Rev. 2008; 108: 3351
    • 10h Jiménez-Númez E, Echavarren AM. Chem. Rev. 2008; 108: 3326
    • 10i Li ZG, Brouwer C, He C. Chem. Rev. 2008; 108: 3239
    • 10j Arcadi A. Chem. Rev. 2008; 108: 3266
    • 10k Hashmi AS. K, Rudolph M. Chem. Soc. Rev. 2008; 37: 1766
    • 10l Rudolph M, Hashmi AS. K. Chem. Soc. Rev. 2012; 41: 2448
    • 10m Echavarren AM. Nat. Chem. 2009; 1: 431
    • 10n Jiménez-Númez E, Echavarren AM. Chem. Commun. 2007; 333
    • 10o Rudolph M, Hashmi AS. K. Chem. Commun 2011; 47: 6536
    • 10p Vachhani DD, Modha SG, Sharma A, Van der Eycken EV. Tetrahedron 2013; 69: 359
  • 11 Modha SG, Vachhani DD, Jacobs J, Van Meervelt L, Van der Eycken EV. Chem. Commun. 2012; 48: 6550
    • 12a Vachhani DD, Mehta VP, Modha SG, Van Hecke K, Van Meervelt L, Van der Eycken EV. Adv. Synth. Catal. 2012; 354: 1593
    • 12b Vachhani DD, Sharma A, Van der Eycken E. J. Org. Chem. 2012; 77: 8768
    • 12c Sharma A, Vachhani D, Van der Eycken E. Org. Lett. 2012; 14: 1854
    • 12d Sharma A, Vachhani D, Van der Eycken E. Chem. Eur. J. 2013; 19: 1158
    • 12e Modha SG, Trivedi JC, Mehta VP, Ermolat’ev DS, Van der Eycken EV. J. Org. Chem. 2011; 76: 846
    • 12f Modha SG, Mehta VP, Ermolat’ev D, Balzarini J, Van Hecke K, Van Meervelt L, Van der Eycken EV. Mol. Divers. 2010; 14: 767
    • 13a Vachhani DD, Sharma A, Van der Eycken E. Angew. Chem. Int. Ed. 2013; 52: 2547
    • 13b Vachhani DD, Kumar A, Modha SG, Sharma SK, Parmar VS, Van der Eycken EV. Eur. J. Org. Chem. 2013; 7: 1223
    • 13c Mehta VP, Modha SG, Ruijter E, Van Hecke K, Van Meervelt L, Pannecouque C, Balzarini J, Orru RV. A, Van der Eycken EV. J. Org. Chem. 2011; 76: 2828
    • 14a Ugi I, Meyr R, Fetzer U, Steinbrucker C. Angew. Chem. 1959; 71: 386
    • 14b Marcaccini S, Torroba T. Nat. Protoc. 2007; 2: 632
    • 14c Ruijter E, Scheffelaar R, Orru RV. A. Angew. Chem. Int. Ed. 2011; 50: 6234
    • 15a Ferrer C, Echavarren AM. Angew. Chem. Int. Ed. 2006; 45: 1105
    • 15b Ferrer C, Amijs CH. M, Echavarren AM. Chem. Eur. J. 2007; 13: 1358
    • 15c Echavarren AM. Nat. Chem. 2009; 1: 431

      For the synthesis of indoloazocines using isonitrile based multicomponent reaction, see:
    • 16a Sinha MK, Khoury K, Herdtweck E, Dömling A. Chem. Eur. J. 2013; 19: 8048
    • 16b Schultz EE, Pujanauski BG, Sarpong R. Org. Lett. 2012; 14: 648
  • 17 For a review on the mechanistic aspects of gold-catalyzed reactions, see: Hashmi AS. K. Angew. Chem. Int. Ed. 2010; 49: 5232