The coupling-isomerization approach to enimines and the first sequential three-component access to 2-ethoxy pyridines

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 59, Issue 4, 2004, Pages 443-450

  Dediu, Oana G ^a   Yehia, Nasser A M ^b   Müller, Thomas J J ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b Morphochem AG   (Germany)

Author keywords

Alkynes; Catalysis; Cross Couplings; Cyclocondensation; Pyridines

Indexed keywords

AMIDES; CATALYSIS; ISOMERS; PYRIDINE;

ALKYNES; CROSS-COUPLINGS; CYCLOCONDENSATION; DIELS-ALDER REACTION; ELECTRON-DEFICIENT; ISOMERIZATION REACTION; ONE-POT REACTION; THREE COMPONENT;

ISOMERIZATION;

ACETAL DERIVATIVE; ALKENE DERIVATIVE; AMIDE; IMINE; N [1 (4 METHOXYPHENYL)PROP 2 YNYL] 4 METHYLBENZENESULFONAMIDE; PYRIDINE DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG;

CONFERENCE PAPER; DIELS ALDER REACTION; ELECTRON; ISOMERIZATION; POLYMERIZATION;

EID: 2442511806     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2004-0413     Document Type: Conference Paper

References (17)

1. a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 4467 (1975);
2. b) K. Sonogashira, in Comprehensive Organic Synthesis, Vol. 3, Chapt. 2.4, Pergamon Press, Oxford (1991);
3. c) K. Sonogashira, in Metal-Catalyzed Cross-Coupling Reactions, p. 203, Wiley-VCH, Weinheim (1998);
4. d) K. Sonogashira, J. Organomet. Chem. 653, 46 (2002).
5. T. J. J. Müller, M. Ansorge, D. Aktah, Angew. Chem. Int. Ed. 39, 1253 (2000).
6. T. J. J. Müller, R. Braun, M. Ansorge, Org. Lett. 2, 1967 (2000).
7. R. U. Braun, K. Zeitler, T. J. J. Müller, Org. Lett. 2, 4181 (2000).
8. R. U. Braun, K. Zeitler, T. J. J. Müller, Org. Lett. 3, 3297 (2001).
9. N. A. M. Yehia, K. Polborn, T. J. J. Müller, Tetrahedron Lett. 43, 6907 (2002).
10. nd ed., p. 91, Elsevier Amsterdam - Oxford - New York-Tokio (1992).
11. All new compounds have been fully characterized spectroscopically and by correct elemental analysis and or HRMS.
12. 1H NMR spectroscopy indicating that the crude mixtures had a purity of ∼ 90%. Upon crystallization or chromatography on silica gel the enimines underwent rapid hydrolysis.
13. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-229839 (3a), CCDC-229838 (3b), and CCDC-229868 (4b). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk).
14. a) J. Sauer, H. Wiest, Angew. Chem. Int. Ed. 1, 268 (1962);
15. b) J. Sauer, R. Sustmann, Angew. Chem. Int. Ed. 19, 779 (1980);
16. c) D. L. Boger, M. Patel, in H. Suschitzky, E. F. V. Scriven (eds): Prog. Heterocyclic Chem., Pergamon Press, Vol. 1, Oxford (1989).
17. Various authors, Organikum, 14th ed., VEB Deutscher Verlag der Wissenschaften, Berlin (1993).