Synthesis of 4-Aminocoumarin derivatives with N-Substitutents containing hydroxy or amino groups

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 68, Issue 9, 2013, Pages 1031-1040

  Ivanov, Ivo C ^a   Angelova, Violina T ^a   Vassilev, Nikolay ^b   Tiritiris, Ioannis ^c   Iliev, Boyan ^d  

^a MEDICAL UNIVERSITY OF SOFIA   (Bulgaria)

^b Institute of Organic Chemistry with Centre of Phytochemistry   (Bulgaria)

^c AALEN UNIVERSITY   (Germany)

^d Ionic Liquids Technologies GmbH   (Germany)

Author keywords

Alkanediamines; Aminoalcohols; Aminocoumarins; Crystal structure; Hydroxycoumarins

Indexed keywords

ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUBSTITUTION REACTIONS;

4-HYDROXYCOUMARIN; ALKANEDIAMINES; AMINOALCOHOLS; AMINOCOUMARINS; E CONFIGURATION; ETHYLENE DIAMINE; HYDROXYCOUMARINS; X-RAY CRYSTAL STRUCTURE ANALYSIS;

CRYSTAL STRUCTURE;

EID: 84883697309     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.5560/ZNB.2013-3102     Document Type: Article

References (40)

1. Y. Jacquot, I. Laïos, A. Cleeren, D. Nonclercq, L. Bermont, B. Refouvelet, K. Boubekeur, A. Xicluna, G. Leclercq, G. Laurent, Bioorg. Med. Chem. 2007, 15, 2269-2282.
2. A. S. Al-Ayed, Molecules 2011, 16, 10292-10302.
3. Y. Dong, K. Nakagawa-Goto, C.-Y. Lai, S. L. Morris-Natschke, K. F. Bastow, K.-H. Lee, Bioorg. Med. Chem. Lett. 2011, 21, 546-549.
4. O. H. Hishmat, A. M. Gohar, M. E.Wassef, M. R. Shalash, I. Ismail, Pharm. Acta Helv. 1977, 52, 252-255.
5. V. Virsdoia, M. S. Shaikh, A. Manvar, B. Desai, A. Parecha, R. Loriya, K. Dholariya, G. Patel, V. Vora, K. Upadhyay, K. Denish, A. Shah, E. C. Coutinho, Chem. Biol. Drug Des. 2010, 76, 412-424.
6. V. L. Savel'ev, N. T. Pryanishnikova, O. S. Artamonova, I. V. Fedina, V. A. Zagorevskii, Pharm. Chem. J. 1975, 9(6), 360-362
7. Khim.-Farm. Zh. 1975, 9, No. (6), 10-12 (in Russian).
8. A. G. Cook, Enamines. Synthesis, Structure and Reactions, Marcel Dekker, New York 1969, pp 396-401.
9. B. Stamboliyska, V. Janevska, B. Shivachev, R. P. Nikolova, G. Stojkovic, B. Mikhova, E. Popovski, Arkivoc 2010, x, 62-76.
10. D. Heber, Arch. Pharm. (Weinheim) 1987, 320, 577-581.
11. I. C. Ivanov, S. K. Karagiosov, M. F. Simeonov, Liebigs Ann. Chem. 1992, 203-208.
12. I. C. Ivanov, S. K. Karagiosov, Synthesis 1995, 633-634.
13. S. Neetha, D. N. Joshipura, M. A. Sridhar, J. S. Prasad, A. Shah, X-Ray Structure Analysis Online 2011, 27, 1-2.
14. V. A. Zagorevskii, V. L. Savel'ev, N. V. Dudykina, J. Org. Chem. USSR (Engl. Transl.) 1968, 4, 1970-1977.
15. V. A. Zagorevskii, V. L. Savel'ev, L. M. Meshcheryakova, Khim. Geterotsikl. Soed. 1970, 6, 1019-1023
16. Chem. Abstr. 1971, 74, 76269c.
17. M. S. Newman, C. Y. Perry, J. Org. Chem. 1963, 28, 116-120.
18. M. A. Kirpichenok, S. K. Gorozhankin, I. I. Grandberg, Chem. Heterocycl. Comp. 1990, 26, 693-697.
19. K. Tabakovi'c, I. Tabakovi'c, N. Ajdini, O. Leci, Synthesis 1987, 308-310.
20. S. D. Joshi, V. D. Sakhardande, S. Seshadri, Indian J. Chem. Sect. B 1984, 23, 206-208.
21. I. C. Ivanov, S. K. Karagiosov, I. Manolov, Arch. Pharm. (Weinheim) 1991, 324, 61-62.
22. E. V. Stoyanov, I. C. Ivanov, Molecules 2004, 9, 627-631.
23. S. R. Moorty, V. Sundaramurthy, N. V. Subba Rao, Indian J. Chem. 1973, 11, 854-856.
24. T. Steinführer, A. Hantschmann, M. Pietsch, M. Weißenfels, Liebigs Ann. Chem. 1992, 23-28.
25. D. Heber, I. C. Ivanov, S. K. Karagiosov, J. Heterocycl. Chem. 1995, 32, 505-509.
26. A. Sabati'e, D. V'egh, A. Loupy, L. Floch, Arkivoc 2001, vi, 122-128.
27. B. I. Iliev, I. C. Ivanov, Molecules 2001, 6, M218.
28. D. Rambabu, G. R. Krishna, C. M. Reddy, M. Pal, Acta Crystallogr. 2010, E66, o2870.
29. J. V. Prasad, J. S. Reddy, N. R. Kumar, K. A. Solomon, G. Gopikrishna, J. Chem. Sci. 2011, 123, 673-679.
30. S. K. Karagiosov, I. C. Ivanov, B. I. Iliev, Molecules 1999, 4, M126.
31. S. Klutchko, J. Shavel, Jr., M. Von Strandtmann, J. Org. Chem. 1974, 39, 2436-2437.
32. P. Ollinger, O. S. Wolfbeis, H. Junek, Darstellung, Monatsh. Chem. 1975, 106, 963-971.
33. F. Risitano, G. Grassi, F. Foti, J. Heterocycl. Chem. 2001, 38, 1083-1086.
34. G. Uray, O. S.Wolfbeis, H. Junek, J. Mol. Struct. 1979, 54, 77-88.
35. V. V. Mulwad, A. S. Hegde, Indian J. Chem. 2009, 48B, 1558-1564.
36. G. M. Sheldrick, SHELXS-97, Program for the Solution of Crystal Structures, University of Göttingen, Göttingen (Germany), 1997.
37. G. M. Sheldrick, Acta Crystallogr. 1990, A46, 467-473.
38. G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen (Germany), 1997.
39. G. M. Sheldrick, Acta Crystallogr. 2008, A64, 112-122.
40. K. Brandenburg, DIAMOND (version 2.1d), Crystal and Molecular Structure Visualization, Crystal Impact-K. Brandenburg & H. Putz GbR, Bonn (Germany) 2000.