Synthesis and reactivity of a novel class of long-lived ammonium ylides: Derivatives of benzo[b]pyrrolo[2,1-f][1.6]naphthyridine

Journal of Organic Chemistry

Volumn 73, Issue 12, 2008, Pages 4596-4601

  Voskressensky, Leonid G ^a   Vorobiev, Ilya V ^a   Borisova, Tatyana N ^a   Varlamov, Alexey V ^a  

^a PEOPLES FRIENDSHIP UNIVERSITY OF RUSSIA   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; AMMONIUM COMPOUNDS; CHEMICAL ACTIVATION; CHEMICAL REACTIONS; CHEMICAL REACTIVITY; HYDROCARBONS; MICROFLUIDICS;

ACTIVATED ALKYNES; AMERICAN CHEMICAL SOCIETY (ACS); AMMONIUM YLIDES; CHEMICAL EQUATIONS; MULTISTAGE PROCESS (MSP); NAPHTHYRIDINE; REACTIVITY (CHEMICAL); SYNTHESIS (OF CHIRAL IONIC LIQUIDS);

SYNTHESIS (CHEMICAL);

ALKYNE DERIVATIVE; AMMONIUM DERIVATIVE; BENZO[B]PYRROLO[2,1 F][1.6]NAPHTHYRIDINE DERIVATIVE; NAPHTHYRIDINE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 45249109110     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8003698     Document Type: Article

References (31)

1. Ho, T. L. In Tandem Organic Reactions; Wiley-Interscience: New York, 1992.
2. Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. 1993, 32, 31.
3. Ziegler, F. E. In Comprehensive Organic Synthesis; Paquette, L. A. Ed.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 7, p 3.
4. (a) Tsuge, O.; Kanemasa, S.; Takenaka, S. Bull. Chem. Soc. Jpn. 1983, 56, 2073.
5. (b) Tsuge, O.; Kanemasa, S.; Takenaka, S. Chem. Lett. 1983, 519.
6. (c) Curran, D. P. Synlett 1991, 63.
7. For selected papers on tandem reactions involving Michael addition see: (a) Shigeta, Y.; Node, M.; Nishide, K.; Shiraki, H.; Obata, K. J. J. Am. Chem. Soc. 2000, 9, 1927.
8. (b) Bunce, R. A.; Herron, D. M.; Ackerman, M. L. J. Org. Chem. 2000, 9, 2847.
9. (c) Trost, B.; Yang, M.; Wuitschik, H. G. Org. Lett. 2005, 21, 4761.
10. (d) Zu, L.; Wang, J.; Li, H.; Xie, H.; Jiang, W.; Wang, W. J. Am. Chem. Soc. 2007, 5, 1036.
11. (e) Jauch, J. J. Org. Chem. 2001, 2, 609.
12. (g) Stelmakh, A.; Stellfeld, T.; Kalesse, M. Org. Lett. 2006, 16, 3485.
13. For selected reviews on tandem reactions, see: (a) Tietze, L. F. Chem. Rev. 1996, 96, 1, 115.
14. (b) Winkler, J. D. Chem. Rev. 1996, 1, 167.
15. (a) Voskressensky, L. G.; Borisova, T. N.; Kulikova, L. N.; Varlamov, A. V.; Catto, M.; Altomare, C.; Carotti, A. Eur. J. Org. Chem. 2004, 3128.
16. (b) Voskressensky, L. G.; Borisova, T. N.; Kostenev, I. S.; Kulikova, L. N.; Varlamov, A. V. Tetrahedron Lett. 2006, 47, 999.
17. Voskressensky, L. G.; Borisova, T. N.; Kostenev, I. S.; Vorobiev, I. V.; Varlamov, A. V. Tetrahedron Lett. 2005, 46, 1975.
18. Gatto, F.; del-Giudice, M. R.; Mustazza, C. J. Heterocycl. Chem. 1996, 33, 1807.
19. For selected papers on Stevens rearrangement, see: (a) Brewster, J. H.; Kline, M. M. J. Am. Chem. Soc. 1953, 74, 5179.
20. (b) Jenney, E. F.; Druey, J. Angew. Chem., Int. Ed. 1962, 1, 155.
21. (c) Blid, J.; Somfai, P. Tetrahedron Lett. 2003, 44, 3159.
22. For a recent review on Stevens rearrangement, see: Vanecko, J. A.; Wan H.; West, F. G. Tetrahedron 2006, 62, 1043.
23. Kostik, E. I.; Abiko, A.; Oku, A. J. Org. Chem. 2001, 66, 1638.
24. Oka, H.; Iida, M.; Sato, J.; Hondd, M. U.S. Patent 6.294.547B.1., 2001.
25. For selected papers on heterocyclic ammonium ylides reactivity, see: (a) Aggarwal, V. K.; Fang, G. Y.; Jonathan, P.; Charmant, H.; Graham, M. Org. Lett. 2003, 5, 1757.
26. (b) Audrey, A.; Larmanjat, B.; Marrot, J.; Couty, F.; David, O. Chem. Commun. 2007, 2500.
27. (c) Robiette, R.; Conza, M.; Aggarwal, V. K. Org. Biomol. Chem. 2006, 4, 621.
28. Chopard, P. A.; Searle, R. J. D.; Devitt, F. H. J. Org. Chem. 1965, 30, 1015.
29. Wang, Y.; Chen, Z.; Mi, A.; Hu, W. Chem. Commun. 2004, 2486.
30. Papageorgiou, C. D.; Cubillo de Dios, M. A.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2004, 35, 4641.
31. Voskressensky, L. G.; Borisova, T. N.; Listratova, A. V.; Vorobiev, I. V.; Alexandrov, G. G.; Varlamov, A. V. J. Heterocycl. Chem. 2005, 42, 1207.