1,3,5-Triazapenta-1,3-dienes: Useful building blocks for the synthesis of 1,2-dihydro-1,3,5-triazines and oligonitriles

European Journal of Organic Chemistry

Volumn , Issue 17, 2006, Pages 3923-3937

  Heße, Nadine ^a   Fröhlich, Roland ^a   Wibbeling, Birgit ^a   Würthwein, Ernst Ulrich ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

1,3,5 Triazapenta 1,3 dienes; DFT calculations; Oligonitriles; Tautomerism; Triazines

Indexed keywords

EID: 33748570752     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600352     Document Type: Article

References (32)

1. N. Heße, R. Fröhlich, I. Humelnicu, E.-U. Würthwein, Eur. J. Inorg. Chem. 2005, 2189-2197.
2. H. Ley, F. Müller, Ber. Dtsch. Chem. Ges. 1907, 40, 2950-2958.
3. H. Behrens, R. Fröhlich, E.-U. Würthwein, Eur. J. Org. Chem. 2005, 3891-3899.
4. M. Buhmann, M. H. Möller, U. Rodewald, E.-U. Würthwein, Angew. Chem. 1994, 106, 2386-2389;
5. Angew. Chem. Int. Ed. Engl. 1994, 33, 2337-2339.
6. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision C.01, Gaussian, Inc., Wallingford, CT, 2004. Details of the quantum-chemical calculations may be obtained from E.-U. W. upon request.
7. W. A. White, H. Weingarten, J. Org. Chem. 1967, 32, 213-214.
8. P. Luthardt, Dissertation, University of Münster 1989.
9. I. Moretti, G. Torre, Synthesis 1970, 141.
10. G. Lowe, C. Carr, R. Quarrell, Chem. Commun. 2001, 737-738.
11. M. Buhmann, M. H. Möller, E.-U. Würthwein, Chem. Ber. 1993, 126, 957-967.
12. M. Buhmann, M. H. Möller, U. Rodewald, E.-U. Würthwein, Chem. Ber. 1993, 126, 2467-2476.
13. J. A. Elvidge, N. R. Borat, in: The Chemistry of Functional Groups, Suppl. A - The Chemistry of Double-Bonded Functional Groups, part 2 (Ed.: S. Patai), Wiley, London 1977, chapter 13.
14. N. C. Aust, R. Fröhlich, J. Hecht, E.-U. Würthwein, Liebigs Ann./Recueil 1997, 1593-1602.
15. A. W. Titherley, E. Worral, J. Chem. Soc. 1910, 97, 839-841.
16. R. Fuks, M. Strebelle, A. Wenders, Synthesis 1977, 788-789.
17. B. I. No, E. V. Shishkin, T. V. Penskaya, V. E. Shishkin, J. Org. Chem. USSR 1996, 32, 1110.
18. P. Grammaticakis, Bull. Soc. Chim. Fr. 1963, 862-872.
19. P. Vossmann, Dissertation, University of Münster, 1999.
20. G. T. Tissue, S. Linke, W. Lwowski, J. Am. Chem. Soc. 1967, 89, 6303-6307.
21. D. Hellwinkel, F. Laemmerzahl, G. Hofmann, Chem. Ber. 1983, 116, 3375-3405.
22. Data sets were collected with Enraf-Nonius CAD4 and Nonius KappaCCD diffractometers, in case of Mo radiation equipped with a rotating anode generator. Programs used: data collection EXPRESS (B. V. Nonius, 1994) and COLLECT (B. V. Nonius. 1998), data reduction MolEN (K. Fair, B. V. Enraf-Nonius. 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326),
23. absorption correction for CCD data SORTAV (R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33-37;
24. R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426),
25. and Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr., Sect. A 2003, 59, 228-234),
26. structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473);
27. structure refinement SHELXL-97 (G. M. Sheldrick, University of Göttingen, 1997), graphics SCHAKAL (E. Keller, 1997). CCDC-298795 (1b), -298797 (1e), -298801 (3a), -298803 (6a), -298804 (6b), -298796 (8a), - 298798 (9a), -600789 (9b), -298799 (11a), -298800 (11b), - 298802 (12a) and -600788 (14) contain 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.
28. F. Cramer, K. Baer, Chem. Ber. 1960, 93, 1231-1236.
29. I. Ugi, F. Beck, U. Fetzer, Chem. Ber. 1962, 95, 126-135.
30. M. Jautelat, K. Ley, Ger. Offen. 1973 DE 22211771, CAN 80:36883.
31. P. Luthardt, M. H. Möller, U. Rodewald, E.-U. Würthwein, Chem. Ber. 1989, 122, 1705-1710.
32. R. R. Schmidt, Chem. Ber. 1965, 98, 334-345.