A novel reaction of the "Huisgen zwitterion" with chalcones and dienones: An efficient strategy for the synthesis of pyrazoline and pyrazolopyridazine derivatives

Angewandte Chemie - International Edition

Volumn 46, Issue 12, 2007, Pages 2070-2073

  Nair, Vijay ^a   Mathew, Smitha C ^a   Biju, Akkattu T ^a   Suresh, Eringathodi ^b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

Chalcones; Nitrogen heterocycles; Pyrazolines synthetic methods; Zwitterions

Indexed keywords

CHALCOGENIDES; POLYCYCLIC AROMATIC HYDROCARBONS; REACTION KINETICS;

DIELS-ALDER REACTION; NITROGEN HETEROCYCLES; PYRAZOLOPYRIDAZINES; ZWITTERIONS;

AMINO ACIDS;

EID: 34250879714     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604025     Document Type: Article

References (22)

1. R. C. Cookson, J. M. Locke, J. Chem. Soc. 1963, 6062-6064.
2. a) E. Brunn, R. Huisgen, Angew. Chem. 1969, 81, 534-536;
3. Angew. Chem. Int. Ed. Engl. 1969, 8, 513-515;
4. b) R. Huisgen in The Adventure Playground of Mechanisms and Novel Reactions: Profiles, Pathways and Dreams (Ed.: J. I. Seeman), American Chemical Society, Washington DC, 1994, p. 62.
5. Reviews: a) O. Mitsunobu, Synthesis 1981, 1-28;
6. b) D. L. Hughes, Org. Prep. Proced. Int. 1996, 28, 127-164;
7. c) T. Watanabe, I. D. Gridnav, T. Imamoto, Chirality 2000, 12, 346-351.
8. T. Kolasa, M. J. Miller, J. Org. Chem. 1987, 52, 4978-4984.
9. Y. Liu, C. Xu, L. Liu, Synthesis 2003, 1335-1338.
10. M. Girard, P. Murphy, N. N. Tsou, Tetrahedron Lett. 2005, 46, 2449-2452.
11. R. D. Otte, T. Sakata, I. A. Guzei, D. Lee, Org. Lett. 2005, 7, 495-498.
12. V. Nair, A. T. Biju, K. G. Abhilash, R. S. Menon, E. Suresh, Org. Lett. 2005, 7, 2121-2123.
13. a) V. Nair, A. T. Biju, A. U. Vinod, E. Suresh, Org. Lett. 2005, 7, 5139-5142;
14. b) V. Nair, A. T. Biju, K. Mohanan, E. Suresh, Org. Lett. 2006, 8, 2213-2216.
15. V. Nair, R. S. Menon, A. R. Sreekanth, N. Abhilash, A. T. Biju, Acc. Chem. Res. 2006, 39, 520-530.
16. CCDC-616377 (6a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. See the Supporting Information for further details.
17. Reviews: a) J. Elguero in Comprehensive Heterocyclic Chemistry, Vol. 5 (Eds.: A. R. Katritzky, C. W. Rees, K. T. Potts), Pergamon, Oxford, 1984, p. 167;
18. b) J. Elguero in Comprehensive Heterocyclic Chemistry II, Vol. 3 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, 1996, p. 1.
19. CCDC-616376 (13a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. See the Supporting Information for further details.
20. a) M. F. Braña, M. Cacho, M. L. García, E. P. Mayoral, B. López, B. Pascual-Teresa, A. Ramos, N. Acero, F. Llinares, D. Muñoz-Mingarro, O. Lozach, L. Meijer, J. Med. Chem. 2005, 48, 6843-6854;
21. b) J. Witherington, V. Bordas, D. Haigh, D. M. B. Hickey, R. J. Ife, A. D. Rawlings, B. P. Slingsby, D. G. Smith, R. W. Ward, Bioorg. Med. Chem. Lett. 2003, 13, 1581 -1584;
22. c) A. K. Tewari, A. Mishra, Bioorg. Med. Chem. 2001, 9, 715-718.