Synthesis of monofluorinated indolizines and their derivatives by the 1,3-dipolar reaction of N-ylides with fluorinated vinyl tosylates

Tetrahedron

Volumn 60, Issue 25, 2004, Pages 5487-5493

  Fang, Xiang ^a,b   Wu, Yong Ming ^a   Deng, Juan ^a   Wang, Shao Wu ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b ANHUI NORMAL UNIVERSITY   (China)

Author keywords

1,3 Dipolar reaction; Fluorinated vinyl tosylate; Monofluorinated indolizines and derivatives; N Ylides; Synthesis

Indexed keywords

1 BENZOYL 2 FLUORO 4 BENZYL 4H PYRROLO[1,2 A]BENZIDIMAZOLE; 1 CYANO 2 FLUORO 4 BENZYL 4H PYRROLO[1,2 A]BENZIDIMAZOLE; 1 ETHOXYCARBONYL 2 FLUORO 4 BENZYL 4H PYRROLO[1,2 A]BENZIDIMAZOLE; 1 FORMYL 3 BENZOYL 8 BROMOINDOLIZINE; 1 FORMYL 3 BENZOYLBENZ[D]INDOLIZINE; 1 FORMYL 3 ETHOXYCARBONYL 8 BROMOINDOLIZINE; 1 FORMYL 3 ETHOXYCARBONYL 8 METHYLINDOLIZINE; 2 BENZYL 3 BENZOYL 6 CYANOINDOLIZINE; 2 FLUORO 3 BENZOYL 6 BROMOINDOLIZINE; 2 FLUORO 3 BENZOYL 6 METHYLINDOLIZINE; 2 FLUORO 3 BENZOYL 7 METHYLINDOLIZINE; 2 FLUORO 3 BENZOYLINDOLIZINE; 2 FLUORO 3 CYANO 6 BROMOINDOLIZINE; 2 FLUORO 3 CYANO 6 METHYLINDOLIZINE; 2 FLUORO 3 CYANO 7 METHYLINDOLIZINE; 2 FLUORO 3 CYANOINDOLIZINE; 2 FLUORO 3 ETHOXYCARBONYL 6 BENZOYLINDOLIZINE; 2 FLUORO 3 ETHOXYCARBONYL 6 BROMOINDOLIZINE; 2 FLUOROBENZOYLBENZ[D]INDOLIZINE; 2 FLUOROCYANOBENZ[D]INDOLIZINE; 2 FLUOROETHOXYCARBONYLBENZ[D]INDOLIZINE; 2,3,3 TRIFLUORO 1 PROPENYLTOSYLATE; BENZIMIDAZOLE; HALIDE; IMIDAZOLE DERIVATIVE; INDOLIZINE DERIVATIVE; ISOQUINOLINE; PYRIDINE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; FLUORINATION; FORMYLATION; PRIORITY JOURNAL;

TRIFLUORO;

EID: 2542421781     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.04.012     Document Type: Article

References (32)

1. Katritzky A.R., Rees C.W. Flitsch W. Comprehensive Heterocyclic Chemistry. Vol. 4:1984;443-495 Pergaman, Oxford
2. Gubin J., Lucchetti J., Nisato D., Rosseeles G., Chinet M., Polster P., Chatelain P. J. Med. Chem. 35:1992;981-988
3. Nugent R.A., Murphy M. J. Org. Chem. 52:1987;2206-2208
4. Smart B.E. Chem. Rev. 96:1996;1555-1584
5. Resnati G., Soloshnok V.A. Tetrahedron. 52:1996;1-8
6. Review: (a) Hudlicky M. Chemistry of Organofluorine Compounds. 2nd ed. 1976;Ellis Horwood, Chichester, England
7. (b) Kodansha; Filler, R.; Kobayashi, Y., Eds., Biomedicinal Aspects of Fluorine Chemistry. Tokyo, 1982.
8. Welch J.T. Tetrahedron. 43:1987;3123-3197
9. Broggini G., Garanti L., Molteni G., Zecchi G. Tetrahedron. 54:1998;2843-3852. and references cited therein
10. Padwa A. 1.3-Diplomar Cycloaddition Chemistry. Vol. 1:1984;Intersciences, New York
11. Banks R.E., Hitchen S.M. J. Fluorine Chem. 20:1982;373-384
12. Banks R.E., Hitchen S.M. J. Chem. Soc., Perkin. Trans. 1. 1982;1593-1600
13. Banks R.E., Hitchen S.M. J. Fluorine Chem. 12:1978;159-166
14. Banks R.E., Mohialdin A. J. Fluorine Chem. 34:1986;275-279
15. Banks R.E., Pritchard R.G., Thomson J. J. Chem. Soc., Perkin. Trans. 1. 1986;1769-1776
16. Banks R.E., Hitchen S.M., Thomson J. J. Fluorine Chem. 20:1982;127-131
17. Banks R.E., Thomson J. J. Fluorine Chem. 22:1982;589-592
18. Banks R.E., Khaffaff S. J. Fluorine Chem. 51:1991;407-418
19. Zhang X.C., Huang W.Y. Tetrahedron Lett. 38:1997;4827-4830
20. Zhang X.C., Huang W.Y. Tetrahedron. 54:1998;12465-12474
21. Zhang X.C., Huang W.Y. J. Fluorine Chem. 87:1998;57-64
22. Zhang X., Huang W.Y. J. Fluorine Chem. 92:1998;13-16
23. Zhang X.C., Huang W.Y. Synthesis. 1999;51-54
24. Wu K., Chen Q.Y. Synthesis. 2003;35-40
25. Zhu S.Z., Qin C.Y., Wang Y.L., Chu Q.L. J. Fluorine Chem. 99:1999;183-187
26. Peng W.M., Zhu S.Z. J. Chem. Soc., Perkin. Trans. 1. 2001;3204-3210
27. Ichikawa J., Wada Y., Fujiwara M., Sakada K. Synthesis. 2002;1917-1920
28. Funabikim K., Tetsuki I., Hiroki Y. J. Chem. Soc., Perkin. Trans. 1. 1998;2413-2442
29. Funabiki K., Ohtsuki T., Ishihara T., Yamanaka H. Chem. Lett. 1994;1075
30. Coe D.G. J. Org. Chem. 24:1959;882-884
31. Wu K., Chen Q.Y. J. Fluorine Chem. 122:2003;171-174
32. The crystal data of 9d has been deposited at the Cambridge Crystallographic Data Center and allocated the deposition number is CCDC 250572