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Microwave-assisted synthesis of fused tricyclic pyrazino[1,2-a]indole derivatives

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Abstract

A microwave-assisted expedient route for the synthesis of novel 3-phenylpyrazino[1,2-a]indol-1(2H)-one derivatives is reported. The method has advantages such as accelerated reaction rate, excellent yields, simplicity of operation, and is eco-friendly. Microwave heating of ammonium acetate generates the NH3 nucleophile required for the cyclization reaction and acetic acid.

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References

  1. Sundberg RJ (1970) The chemistry of indoles, vol 18. Academic Press, New York

  2. Sundberg RJ (1984) Pyrroles and their benzoderivatives: synthesis and applications. In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry, vol 4. Pergamon, Oxford, p 313

    Chapter  Google Scholar 

  3. Sundberg RJ (1996) Indoles: best synthetic methods, vol 7. Academic, New York

  4. Joule JA (2000) Indole and its derivatives. In: Thomas EJ (ed) Houben-Weyl—science of synthesis, vol 10. Thieme, Stuttgart, Chap 10.13

    Google Scholar 

  5. Brown RK (1972) In: Houlihan WJ (ed) Indoles. Wiley-Interscience, New York

    Google Scholar 

  6. Evans BE, Rittle KE, Bock MG, DiPardo RM, Freidinger RM, Whitter WL, Lundell GF, Verber DF, Anderson PS, Chang RSL, Lotti VJ, Cerino DH, Chen TB, Kling PJ, Kunkel KA, Springer JP, Hirshfield J (1988) J Med Chem 31:2235

    Article  CAS  Google Scholar 

  7. Horton DA, Bourne GT, Smythe ML (2003) Chem Rev 103:893

    Article  CAS  Google Scholar 

  8. Gribble GW (2000) J Chem Soc Perkin Trans 1:1045

    Article  Google Scholar 

  9. Pindur U, Dam R (1988) J Heterocycl Chem 25:1

    Article  CAS  Google Scholar 

  10. Gilchrist TL (2001) J Chem Soc Perkin Trans 1:2491

    Article  Google Scholar 

  11. Guy RH, Jeffrey TK (2006) Chem Rev 106:2875

    Article  Google Scholar 

  12. Ruppelt M, Bartel S, Guarnieri W, Raddatz S, Rosentreter U, Wild H, Endermann R, Kroll HP (1999) Synthesis and antibacterial activity of substituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles. German Patent DE 19802235, 29 Jul 1999 (Chem Abstr 131:129985)

  13. McCort G, Hoornaert C, Duclos O, Guilpain E, Cadilhac C, Dellac G (1998) Synthesis and antibacterial activity of substituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles. French Patent FR 2761073, 25 Sep 1998 (Chem Abstr 130:38400)

  14. Commons TJ, Laclair CM, Christman S (1996) Synthesis and antifungal activity of substituted 10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indoles. PCT Int Appl WO 9612721, 2 May 1996 (Chem Abstr 125:114494u)

  15. Freed ME (1977) Synthesis and antibacterial activity of substituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles. US Patent 4022778, 10 May 1977 (Chem Abstr 87:68421q)

  16. Mokrosz JL, Duszynska B, Paluchowska MH (1994) Arch Pharm 8:529

    Article  CAS  Google Scholar 

  17. Basanagoudar LD, Mahajanshetti CS, Hendi SB, Dambal SB (1991) Indian J Chem 30b:1014

    CAS  Google Scholar 

  18. Rajur SB, Merwade AY, Hendi SB, Basanagoudar LD (1989) Indian J Chem 28b:1065

    CAS  Google Scholar 

  19. Bit RA, Davis PD, Elliott LH, Harris W, Hill CH, Keech E, Kumar H, Lowton G, Maw A, Nixon JS, Vesey DR, Wadsworth J, Wilkinson SE (1993) J Med Chem 36:21

    Article  CAS  Google Scholar 

  20. Fong CJ, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA (2002) Bioorg Med Chem Lett 12:155

    Article  Google Scholar 

  21. Bos M, Jenck F, Martin JR, Moreau JL, Mutel V, Sleight AJ, Widmer U (1997) Eur J Med Chem 32:253

    Article  CAS  Google Scholar 

  22. Glennon RA, Grella B, Tyacke RJ, Lau A, Westaway J, Hudson AL (2004) Bioorg Med Chem Lett 14:999

    Article  CAS  Google Scholar 

  23. Tiwari RK, Verma AK, Chhillar AK, Singh D, Singh J, Sankar KV, Yadav V, Sharma GL, Chandra R (2006) Bioorg Med Chem 14:2747

    Article  CAS  Google Scholar 

  24. Tiwari RK, Singh D, Singh J, Pathak AK, Dabur R, Chhillar AK, Singh R, Sharma GL, Chandra R, Verma AK (2006) Bioorg Med Chem Lett 16:413

    Article  CAS  Google Scholar 

  25. McCort G, Hoornaert C, Cadilhac C, Duclos O, Guilpain E, Dellac G (1998) Dihydropyrazino[1,2-a]indole-1-one derivatives, preparation and application thereof in therapeutics. PCT Int Appl WO 9842710, 1 Oct 1998 (Chem Abstr 129:275933)

  26. Romagnoli R, Baraldi PG, Carrion MD, Cruz-Lopez O, Cara CL, Delia P, Mojgan AT, Jan B, Ernest H, Enrica F, Roberto G (2009) Lett Drug Des Discov 6:298

    Article  CAS  Google Scholar 

  27. Tsyshkova NG, Trofimov FA, Marinchenko VP, Dubovik BV, Lushniknova GA, Shvedov VI (1992) Khim Farm Zh 26:70

    CAS  Google Scholar 

  28. Abbiati G, Beccalli EM, Broggini G, Zoni C (2003) J Org Chem 68:7625

    Article  CAS  Google Scholar 

  29. Röver S, Adams DR, Bénardeau A, Bentley JM, Bickerdike MJ, Bourson A, Cliffe IA, Coassolo P, Davidson JEP, Dourish CT, Hebeisen P, Kennett GA, Knight AR, Malcolm CS, Mattei P, Misra A, Mizrahi J, Muller M, Porter RHP, Richter H (2005) Bioorg Med Chem Lett 15:3604

    Article  Google Scholar 

  30. John RJ, Aubrey AL, Ann DH, Koert G (1947) J Am Chem Soc 69:2364

    Article  Google Scholar 

  31. Margaret AB, Andrew DJ (1994) Tetrahedron 50:4887

    Article  Google Scholar 

  32. Loupy A (ed) (2006) Microwaves in organic synthesis. Wiley-VCH, Weinheim

    Google Scholar 

  33. de la Hoz A, Diaz-Ortiz A, Moreno A (2007) Chem Soc Rev 107:2563

    Google Scholar 

  34. Lidsstrom P, Tierney J, Wathey B, Westman J (2001) Tetrahedron 57:9225

    Article  Google Scholar 

  35. Loones KTJ, Maes BUW, Rombouts G, Hostyn S, Gaston D (2005) Tetrahedron 61:10338

    Article  CAS  Google Scholar 

  36. Cherukupally P, Javvaji RR, Padi PR, Kaga M, Gade SR (2008) J Heterocycl Chem 45:1083

    Article  Google Scholar 

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Acknowledgments

The authors thank Council for Scientific and Industrial Research (CSIR) New Delhi for financial assistance for this work and the Principal, K. T. H. M. College, Nashik - 422 002 for facilities.

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Correspondence to Raghunath Toche.

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Toche, R., Chavan, S. & Janrao, R. Microwave-assisted synthesis of fused tricyclic pyrazino[1,2-a]indole derivatives. Monatsh Chem 145, 1507–1512 (2014). https://doi.org/10.1007/s00706-014-1216-7

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  • DOI: https://doi.org/10.1007/s00706-014-1216-7

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