Synthesis 2013; 45(7): 971-977
DOI: 10.1055/s-0032-1318273
paper
© Georg Thieme Verlag Stuttgart · New York

Recyclization in the Series of Spiro[indole-3,5′-pyrimido[4,5-b]quinoline]-2,2′,4′-triones Prepared by a Three-Component Reaction of Isatins with (Thio)barbituric Acids and Electron-Rich Anilines

Viktor O. Iaroshenko*
a   Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany   Email: viktor.iaroshenko@uni-rostock.de   Email: iva108@googlemail.com
b   National Taras Shevchenko University, 62 Volodymyrska Str., 01033 Kyiv, Ukraine
,
Sergii Dudkin
a   Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany   Email: viktor.iaroshenko@uni-rostock.de   Email: iva108@googlemail.com
,
Vyacheslav Ya. Sosnovskikh
c   Department of Chemistry, Ural Federal University, 51 Lenina Ave., 620000 Ekaterinburg, Russian Federation
,
Alexander Villinger
a   Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany   Email: viktor.iaroshenko@uni-rostock.de   Email: iva108@googlemail.com
,
Peter Langer
a   Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany   Email: viktor.iaroshenko@uni-rostock.de   Email: iva108@googlemail.com
d   Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert Einstein Str. 29a, 18059 Rostock, Germany
› Author Affiliations
Further Information

Publication History

Received: 10 December 2012

Accepted after revision: 30 January 2013

Publication Date:
14 February 2013 (online)


Abstract

A ring–ring transformation in the series of spiro[indole-3,5′-pyrimido[4,5-b]quinoline]-2,2′,4′-trione derivatives prepared by a three-component reaction of (thio)barbituric acids, electron-rich aromatic amines, and isatins was observed.

Supporting Information

 
  • References

  • 1 Miller KA, Williams RM. Chem. Soc. Rev. 2009; 38: 3160
    • 2a Jossang A, Jossang P, Hadi HA, Sévenet T, Bodo B. J. Org. Chem. 1991; 56: 6527
    • 2b Cui C.-B, Kakeya H, Osada H. Tetrahedron 1996; 52: 12651
  • 3 Codner E, Cassorla F, Tiulpakov AN, Mericq MV, Avila A, Pescovitz OH, Svensson J, Cerchio K, Krupa D, Gertz BJ, Murphy G. Clin. Pharmacol. Ther. 2001; 70: 91
  • 4 Brown MJ, Palmer CR, Castaigne A, de Leeuw PW, Mancia G, Rosenthal T, Ruilope LM. Lancet 2000; 356: 366
  • 5 Lu H, Klein RS, Schwartz EL. Clin. Cancer Res. 2009; 15: 5136
    • 6a Shi F, Zhou D, Tu S, Li C, Cao L, Shao Q. J. Heterocycl. Chem. 2008; 45: 1305
    • 6b Capuano L, Diehl V. Chem. Ber. 1976; 109: 723
    • 6c Shi D.-Q, Ni S.-N, Yang F, Shi J.-W, Dou G.-L, Li X.-Y, Wang X.-S, Ji S.-J. J. Heterocycl. Chem. 2008; 45: 693
    • 6d Khalafi-Nezhad A, Panahi F. Synthesis 2011; 984
    • 6e Hassan NA, Hegab MI, Hashem AI, Abdel-Motti FM, Hebah SH. A, Abdel-Megeid FM. E. J. Heterocycl. Chem. 2007; 44: 775
    • 6f Tisseh ZN, Ahmadi F, Dabiri M, Khavasi HR, Bazgir A. Tetrahedron Lett. 2012; 53: 3603
    • 6g Khorrami AR, Kiani P, Bazgir A. Monatsh. Chem. 2011; 142: 287
    • 6h Vilches-Herrera M, Knepper I, de Souza N, Villinger A, Sosnovskikh VY, Iaroshenko VO. ACS Comb. Sci. 2012; 14: 434
    • 6i Ahadi S, Moafi L, Feiz A, Bazgir A. Tetrahedron 2011; 67: 3954
    • 6j Yang X, Yang L, Wu L. Bull. Korean Chem. Soc. 2012; 33: 714
    • 6k Chen H, Shi D. J. Comb. Chem. 2010; 12: 571
    • 6l Shakibaei GI, Feiz A, Khavasi HR, Soorki AA, Bazgir A. ACS Comb. Sci. 2011; 13: 96
    • 7a Iaroshenko VO, Sevenard DV, Kotljarov A, Volochnyuk DM, Tolmachev A, Sosnovskikh VY. Synthesis 2009; 731
    • 7b Iaroshenko VO, Wang Y, Sevenard DV, Volochnyuk D. Synthesis 2009; 1851
    • 7c Iaroshenko VO, Sevenard DV, Volochnyuk DM, Wang Y, Martiloga A, Tolmachev AO. Synthesis 2009; 1865
    • 7d Iaroshenko VO, Wang Y, Zhang B, Volochnyuk D, Sosnovskikh VY. Synthesis 2009; 2393
    • 7e Kotljarov A, Irgashev RA, Iaroshenko VO, Sevenard DV, Sosnovskikh VY. Synthesis 2009; 3233
    • 7f Kotljarov A, Iaroshenko VO, Volochnyuk DM, Irgashev RA, Sosnovskikh VY. Synthesis 2009; 3869
    • 7g Iaroshenko VO, Ostrovskyi D, Petrosyan A, Mkrtchyan S, Villinger A, Langer P. J. Org. Chem. 2011; 76: 2899
    • 7h Iaroshenko VO, Bunescu A, Spannenberg A, Langer P. Chem. Eur. J. 2011; 17: 7188
    • 7i Iaroshenko VO, Mkrtchyan S, Villinger A. Synthesis 2013; 45: 205
    • 7j Iaroshenko VO, Vilches-Herrera M, Gevorgyan A, Arakelyan K, Ostrovskyi D, Abbasi MS. A, Mkrtchyan S, Supe L, Hakobyan A, Villinger A, Volochnyuk DM, Tolmachev A. Tetrahedron 2013; 69: 1217
  • 8 Lu GP, Cai C. J. Chem. Res. 2011; 35: 547
    • 9a Ghahremanzadeh R, Moghaddam MM, Bazgir A, Akhondi MM. Chin. J. Chem. 2012; 30: 321
    • 9b Chen T, Xu X.-P, Ji S.-J. J. Comb. Chem. 2010; 12: 659
    • 9c Quiroga J, Portillo S, Pérez A, Gálvez J, Abonia R, Insuasty B. Tetrahedron Lett. 2011; 52: 2664
    • 9d Rahmati A, Khalesi Z. Tetrahedron 2012; 68: 8472
    • 9e Shirvan SA, Ghahremanzadeh R, Moghaddam MM, Bazgir A, Zarnani AH, Akhondi MM. J. Heterocycl. Chem. 2012; 49: 951
    • 9f Ghahremanzadeh R, Sayyafi M, Ahadi S, Bazgir A. J. Comb. Chem. 2009; 11: 393
    • 9g Jadidi K, Ghahremanzadeh R, Bazgir A. J. Comb. Chem. 2009; 11: 341
  • 10 da Silva JF. M, Garden SJ, Pinto AC. J. Braz. Chem. Soc. 2001; 12: 273
  • 11 Wang X.-S, Li Q, Wu J.-R, Zhang M.-M. Synth. Commun. 2009; 39: 3069
  • 12 Jursic BS, Stevens ED. Tetrahedron Lett. 2002; 43: 5681
    • 13a Dabiri M, Azimi SC, Khavasi HR, Bazgir A. Tetrahedron 2008; 64: 7307
    • 13b Ghahremanzadeh R, Azimi SC, Gholami N, Bazgir A. Chem. Pharm. Bull. 2008; 56: 1617
  • 14 Crystallographic data (excluding structure factors) for the structures 5b, 5f, and 8 reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 921314–921316 and can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk, or via www.ccdc.cam.ac.uk/data_request/cif.
    • 15a Kefayati H, Narchin F, Rad-Moghadam K. Tetrahedron Lett. 2012; 53: 4573
    • 15b Jiang B, Wang X, Li M.-Y, Wu Q, Ye Q, Xu H.-W, Tu S.-J. Org. Biomol. Chem. 2012; 10: 8533