Synlett 2015; 26(05): 604-608
DOI: 10.1055/s-0034-1379950
letter
© Georg Thieme Verlag Stuttgart · New York

Target cum Flexibility: Synthesis of Indolo[1,2-b]isoquinoline Derivatives via Cobalt-Catalyzed [2+2+2] Cyclotrimerization

Anuradha Swami
Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, India   eMail: vr.chepuri@ncl.res.in
,
Chepuri V. Ramana*
Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, India   eMail: vr.chepuri@ncl.res.in
› Institutsangaben
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Publikationsverlauf

Received: 03. Oktober 2014

Accepted after revision: 26. November 2014

Publikationsdatum:
12. Januar 2015 (online)


Abstract

A modular approach for the synthesis of small molecules having the unnatural 6,11-dihydroindolo[1,2-b]isoquinoline tetracyclic core has been documented. An acid-catalyzed Friedel–Crafts-type C2-alkylation of N-propargyl indole with a suitably activated alkynol has been used to prepare the key indole-derived diynes. The cobalt-catalyzed [2+2+2] cyclotrimerization of these diynes has been studied with various internal/terminal alkynes and with nitriles.

Supporting Information

 
  • References

    • 1a Welsch ME, Snyder SA, Stockwell BR. Curr. Opin. Chem. Biol. 2010; 14: 347
    • 1b Kumar K, Waldmann H. Angew. Chem. Int. Ed. 2009; 48: 3224
    • 1c Nielsen TE, Schreiber SL. Angew. Chem. Int. Ed. 2008; 47: 48

      Selected examples on the use of cycloaddition in diversity-oriented synthesis, see:
    • 2a Bauer RA, DiBlasi CM, Tan DS. Org. Lett. 2010; 12: 2084
    • 2b Zhou LS, Li S, Kanno K, Takahashi T. Heterocycles 2010; 80: 725
    • 2c Yuan CX, Chang CT, Axelrod A, Siegel D. J. Am. Chem. Soc. 2010; 132: 5924
    • 2d Komine Y, Tanaka K. Org. Lett. 2010; 12: 1312
    • 2e Komine Y, Kamisawa A, Tanaka K. Org. Lett. 2009; 11: 2361
    • 2f Kotha S, Khedkar P. Eur. J. Org. Chem. 2009; 730
    • 2g Gray BL, Wang X, Brown WC, Kuai L, Schreiber SL. Org. Lett. 2008; 10: 2621 From our group
    • 2h Dushing MP, Ramana CV. Tetrahedron Lett. 2011; 52: 4627
    • 2i Ramana CV, Dushing MP, Mohapatra S, Mallik R, Gonnade RG. Tetrahedron Lett. 2011; 52: 38

      For selected reviews, see:
    • 3a Vollhardt KP. C. Acc. Chem. Res. 1977; 10: 1
    • 3b Vollhardt KP. C. Angew. Chem., Int. Ed. Engl. 1984; 23: 539
    • 3c Lautens M, Klute W, Tam W. Chem. Rev. 1996; 96: 49
    • 3d Saito S, Yamamoto Y. Chem. Rev. 2000; 100: 2901
    • 3e Varela JA, Saa C. Chem. Rev. 2003; 103: 3787
    • 3f Kotha S, Brahmachary E, Lahiri K. Eur. J. Org. Chem. 2005; 4741
    • 3g Chopade PR, Louie J. Adv. Synth. Catal. 2006; 348: 2307
    • 3h Shibata T, Tsuchikama K. Org. Biomol. Chem. 2008; 6: 1317
    • 3i Tanaka K. Chem. Asian J. 2009; 4: 508
    • 3j Inglesby PA, Evans PA. Chem. Soc. Rev. 2011; 39: 2791
    • 3k Dominguez G, Perez-Castells J. Chem. Soc. Rev. 2011; 40: 3430
    • 3l Hsu SF, Ko CW, Wu YT. Adv. Synth. Catal. 2011; 353: 2881
    • 3m Weding N, Hapke M. Chem. Soc. Rev. 2010; 40: 4525
    • 3n Broere DL. J, Ruijter E. Synthesis 2012; 44: 2639
    • 3o Shibata Y, Tanaka K. Synthesis 2012; 44: 323

      For recent total synthesis employing [2+2+2] cyclotrimerization, see:
    • 4a Alayrac C, Schollmeyer D, Witulski B. Chem. Commun. 2009; 1464
    • 4b Witulski B, Zimmermann A, Gowans ND. Chem. Commun. 2002; 2984
    • 4c Anderson EA, Alexanian EJ, Sorensen EJ. Angew. Chem. Int. Ed. 2004; 43: 1998
    • 4d Ramana CV, Salian SR, Gonnade RG. Eur. J. Org. Chem. 2007; 5483
    • 4e Nicolaou KC, Wang J, Tang Y, Botta L. J. Am. Chem. Soc. 2010; 132: 11350
    • 4f Zou Y, Deiters A. J. Org. Chem. 2010; 75: 5355
    • 4g Dallinger D, Irfan M, Suljanovic A, Kappe CO. J. Org. Chem. 2010; 75: 5278
    • 5a Ishikura M, Abe T, Choshi T, Hibino S. Nat. Prod. Rep. 2013; 30: 694
    • 5b Kochanowska-Karamyan AJ, Hamann MT. Chem. Rev. 2010; 110: 4489
    • 6a Pesnot T, Gershater MC, Ward JM, Hailes HC. Chem. Commun. 2011; 3242
    • 6b Vennerstrom JL, Klayman DL. J. Med. Chem. 1988; 31: 1084
    • 6c Scott JD, Williams RM. Chem. Rev. 2002; 102: 1669
    • 6d Magnus P, Matthews KS. Tetrahedron 2012; 68: 6343
    • 6e Bentley KW. Nat. Prod. Rep. 2005; 22: 249
    • 6f Amat M, Elias V, Llor N, Subrizi F, Molins E, Bosch J. Eur. J. Org. Chem. 2010; 4017
    • 6g Rotte SC. K, Chittiboyina AG, Khan IA. Eur. J. Org. Chem. 2013; 6355
    • 7a Chang MX, Li W, Zhang XM. Angew. Chem. Int. Ed. 2011; 50: 10679
    • 7b Zou ZH, Lan XB, Qian H, Huang WL, Li YM. Bioorg. Med. Chem. Lett. 2011; 21: 5934
    • 7c Lebrun S, Couture A, Deniau E, Grandclaudon P. Eur. J. Org. Chem. 1999; 2345
    • 8a Hazra S, Mondal B, Rahaman H, Roy B. Eur. J. Org. Chem. 2014; 2806
    • 8b Sun J, Zhang LL, Yan CG. Tetrahedron 2013; 69: 5451
    • 9a Vincze Z, Biro AB, Csekei M, Timari G, Kotschy A. Synthesis 2006; 1375
    • 9b Orito K, Miyazawa M, Kanbayashi R, Tokuda M, Suginome H. J. Org. Chem. 1999; 64: 6583
    • 9c Lotter AN. C, Pathak R, Sello TS, Fernandes MA, van Otterlo WA. L, de Koning CB. Tetrahedron 2007; 63: 2263
    • 9d Goldbrunner M, Loidl G, Polossek T, Mannschreck A, von Angerer E. J. Med. Chem. 1997; 40: 3524
    • 9e Shukla SP, Tiwari RK, Verma AK. J. Org. Chem. 2012; 77: 10382
  • 10 Takaya J, Udagawa S, Kusama H, Iwasawa N. Angew. Chem. Int. Ed. 2008; 47: 4906
  • 11 Sanz R, Ignacio JM, Castroviejo MP, Fañanás FJ. ARKIVOC 2007; (iv): 84
  • 12 Alicea J, Wolfe JP. J. Org. Chem. 2014; 79: 4212
    • 13a Bennasar ML, Roca T, Ferrando F. Org. Lett. 2004; 6: 759
    • 13b Gilchrist TL, Kemmitt PD, Germain AL. Tetrahedron 1997; 53: 4447
    • 14a Srivastava A, Singh S, Samanta S. Tetrahedron Lett. 2013; 54: 1444
    • 14b Rueping M, Nachtsheim BJ. Beilstein J. Org. Chem. 2010; 6: 1
    • 14c Bandini M, Eichholzer A. Angew. Chem. Int. Ed. 2009; 48: 9608
    • 14d Le Bras J, Muzart J. Tetrahedron 2007; 63: 7942
    • 14e Bandini M, Tragni M. Org. Biomol. Chem. 2009; 7: 1501
    • 15a Sanz R, Gohain M, Miguel D, Martinez A, Rodriguez F. Synlett 2009; 1985
    • 15b Sanz R, Miguel D, Martinez A, Gohain M, Garcia-Garcia P, Fernandez-Rodriguez MA, Alvarez E, Rodriguez F. Eur. J. Org. Chem. 2010; 7027

      Selected reports on Co-mediated cyclotrimerizations:
    • 16a Hillard III RL, Vollhardt KP. C. Angew. Chem., Int. Ed. Engl. 1975; 14: 712
    • 16b Stara IG, Stary I, Kollarovic A, Teply F, Saman D, Tichy M. J. Org. Chem. 1998; 63: 4046
    • 16c Fatland AW, Eaton BE. Org. Lett. 2000; 2: 3131
    • 16d Fletcher AJ, Christie SD. R. J. Chem. Soc., Perkin Trans. 1 2000; 1657
    • 16e Chouraqui G, Petit M, Aubert C, Malacria M. Org. Lett. 2004; 6: 1519
    • 16f Maryanoff BE, Zhang H.-C. ARKIVOC 2007; (xii): 7
    • 16g Young DD, Deiters A. Angew. Chem. Int. Ed. 2007; 46: 5187
    • 16h Geny A, Agenet N, Iannazzo L, Malacria M, Aubert C, Gandon V. Angew. Chem. Int. Ed. 2009; 48: 1810
    • 16i Varela JA, Saa C. J. Organomet. Chem. 2009; 694: 143
    • 16j McIver AL, Deiters A. Org. Lett. 2010; 12: 1288
  • 17 Sanz R, Martinez A, Alvarez-Gutierrez JM, Rodriguez F. Eur. J. Org. Chem. 2006; 1383