Microwave-Assisted One-Pot Synthesis
of (Aminoalkyl)naphthols and (Aminoalkyl)quinolinols by
Using Ammonium Carbamate or Ammonium Hydrogen Carbonate
as Solid Ammonia Source

István Szatmári; Ferenc Fülöp

doi:10.1055/s-0028-1083347

PAPER

Microwave-Assisted One-Pot Synthesis of (Aminoalkyl)naphthols and (Aminoalkyl)quinolinols by Using Ammonium Carbamate or Ammonium Hydrogen Carbonate as Solid Ammonia Source

István Szatmári, Ferenc Fülöp*
Institute of Pharmaceutical Chemistry and Research Group for Stereochemistry, Hungarian Academy of Sciences, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary
Fax: +36(62)545705; e-Mail: fulop@pharm.u-szeged.hu;

Abstract

Alle Artikel dieser Rubrik

Abstract

Ammonium carbamate and ammonium hydrogen carbonate were used as very effective solid ammonia sources to prepare different (aminoalkyl)naphthols and (aminoalkyl)quinolinols in ethanol and water as solvents under microwave conditions in modified three-component Mannich reactions. The products were obtained in excellent yields in one-pot reactions.

Key words

amino alcohols - green chemistry - heterocycles - Mannich bases - multicomponent reactions

Volltext

Referenzen

References

1 Szatmári I. Fülöp F. Curr. Org. Synth. 2004, 1: 155

2 Cardellicchio C. Ciccarella G. Naso F. Schingaro E. Scordari F. Tetrahedron: Asymmetry 1998, 9: 3667

3 Cardellicchio C. Ciccarella G. Naso F. Perna F. Tortorella P. Tetrahedron 1999, 55: 14685

4 Cimarelli C. Mazzanti A. Palmieri G. Volpini E. J. Org. Chem. 2001, 66: 4759

5 Liu D.-X. Zhang L.-C. Wang Q. Da C S. Xin Z.-Q. Wang R. Choi MCK. Chan ASC. Org. Lett. 2001, 3: 2733

6 Cimarelli C. Palmieri G. Volpini E. Tetrahedron: Asymmetry 2002, 13: 2417

7 Ji J.-X. Qiu L.-Q. Yip CW. Chan ASC. J. Org. Chem. 2003, 68: 1589

8 Ji J.-X. Wu J. Au-Yeung TTL. Yip CW. Haynes RK. Chan ASC. J. Org. Chem. 2005, 70: 1093

9 Cappanini L. Cimarelli C. Giuli S. Palmieri G. Petrini M. Tetrahedron: Asymmetry 2007, 18: 1022

10 Duff C. Bills JE. J. Chem. Soc. 1934, 1305

11 Szatmári I. Hetényi A. Lázár L. Fülöp F. J. Heterocycl. Chem. 2004, 41: 367

12 Heydenreich M. Koch A. Klod S. Szatmári I. Fülöp F. Kleinpeter E. Tetrahedron 2006, 62: 11081

13 Szatmári I. Martinek TA. Lázár L. Fülöp F. Tetrahedron 2003, 59: 2877

14 Szatmári I. Tóth D. Koch A. Heydenreich M. Kleinpeter E. Fülöp F. Eur. J. Org. Chem. 2006, 4670

15 Szatmári I. Martinek TA. Lázár L. Fülöp F. Eur. J. Org. Chem. 2004, 2231

16 Turgut Z. Pelit E. Köycü A. Molecules 2007, 12: 345

17 Tóth D. Szatmári I. Fülöp F. Eur. J. Org. Chem. 2006, 4664

18 Shen AY. Tsai CT. Chen CL. Eur. J. Med. Chem. 1999, 34: 877

19 Shaterian HR. Yarahmadi H. Ghashang M. Bioorg. Med. Chem. Lett. 2008, 18: 788

20 Bryson TA. Stewart JJ. Gibson JM. Thomas PS. Berch JK. Green Chem. 2003, 5: 174

21 El Kaim L. Gautier L. Grimaud L. Harwood LM. Michaut V. Green Chem. 2003, 5: 477

22 Shimizu S. Shimada N. Sasaki Y. Green Chem. 2006, 8: 608

23 Zhang J. Cui Z. Wang F. Wang Y. Miao Z. Chen R. Green Chem. 2007, 9: 1341

24 Litvić M. Filipan M. Pogorelić I. Cepanec I. Green Chem. 2005, 7: 771

25 Ammonium carbamate is not stable above 60 ˚C, and decomposes, affording gaseous ammonia and carbon dioxide; see: The Merck Index 12th ed.: Merck Research Laboratories; Whitehouse Station NJ: 1996.

26 Phillips JP. Keown R. Fernando Q. J. Am. Chem. Soc. 1953, 75: 4306

27 Phillips JP. Keown R. Fernando Q. J. Org. Chem. 1954, 19: 907

28 Saidi MR. Azizi N. Naimi-Jamal MR. Tetrahedron Lett. 2001, 42: 8111

29 Robin Y. Godard A. Queguiner G. J. Heterocycl. Chem. 1987, 24: 1487

30 Jacquelin JM. Robin Y. Godard A. Queguiner G. Can. J. Chem. 1988, 66: 1135

31 Lu Y. Nikolovska-Coleska Z. Fang X. Gao W. Shangary S. Qiu S. Qin D. Wang S. J. Med. Chem. 2006, 49: 3759