Collect. Czech. Chem. Commun.
2004, 69, 242-260
https://doi.org/10.1135/cccc20040242
Synthesis and Electrochemical Reduction of Methyl 3-Halo-1-benzothiophene-2-carboxylates
Michal Rejňáka,b, Jiří Klímab, Jiří Svobodaa and Jiří Ludvíkb,*
a Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
b J. Heyrovský Institute of Physical Chemistry and Electrochemistry, Academy of Sciences of the Czech Republic, Dolejškova 3, 182 23 Prague 8, Czech Republic
References
1. Chem. Rev. 1995, 95, 2457.
< N., Suzuki A.: https://doi.org/10.1021/cr00039a007>
2. Acc. Chem. Res. 1982, 15, 340.
< E.: https://doi.org/10.1021/ar00083a001>
3. Pure Appl. Chem. 1996, 68, 73.
< V.: https://doi.org/10.1351/pac199668010073>
4. Synthesis 1974, 9.
< P. E.: https://doi.org/10.1055/s-1974-23219>
5. Houben–Weyl: Methods of Organic Chemistry, Vol. E21a, Stereoselective Synthesis (G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Eds). G. Thieme Verlag, Stuttgart 1995.
6. Acc. Chem. Res. 1990, 23, 345.
< R., Takaya H.: https://doi.org/10.1021/ar00178a005>
7. J. Org. Chem. 1996, 61, 6244.
< T., Brenna E., Sannicolo F., Trimarco L., Antognazza P., Cesarotti E., Demartin F., Pilati T.: https://doi.org/10.1021/jo960211f>
8. J. Org. Chem. 1985, 50, 4062.
< G., Zimmermann R.: https://doi.org/10.1021/jo00221a020>
9. Angew. Chem., Int. Ed. Engl. 1996, 35, 1533.
< G., Hugelé P., Bartsch R., Skoulios A.: https://doi.org/10.1002/anie.199615331>
10. J. Org. Chem. 1998, 63, 3895.
< G., Hugele P., Bartsch R.: https://doi.org/10.1021/jo972143i>
11. Collect. Czech. Chem. Commun. 2003, 68, 1020.
< M., Petříčková H., Maloň P., Svoboda J.: https://doi.org/10.1135/cccc20031020>
12. Cesk. Farm. 1999, 48, 281.
M., Havelková M., Terinek M., Paleček J., Svoboda J., Jandera A., Panajotová V., Kuchař M.:
13. J. Org. Chem. 1976, 41, 3399.
< T., Krubsack A. J.: https://doi.org/10.1021/jo00883a014>
14. Zh. Org. Khim. 1975, 11, 1776.
I., Zborovskii Y. L.:
15. Chem. Ber. 1955, 88, 34.
< W., Bender H.: https://doi.org/10.1002/cber.19550880107>
16. Synthesis 1980, 327.
< M. G., Newsom J. G., Almqvist K. A.: https://doi.org/10.1055/s-1980-29015>
17. Trends Org. Chem. 1992, 3, 173.
J.-Y., Perichon J.:
18. Izv. Akad. Nauk, Ser. Khim. 1979, 7, 1576.
V. P., Proskurovskaya I. V., Rubinskaya T. Ya., Lozanova A. V., Moiseenkov A. M., Semenovskii A. V.:
19. J. Org. Chem. 1986, 51, 3468.
< R. I., Miller E. K.: https://doi.org/10.1021/jo00368a012>
20. Elektrokhimiya 1979, 15, 118.
S. G., Kosychenko L. I., Litvinov V. P.:
21. J. Pharm. Sci. 1963, 52, 55.
< L. W., Krupski E.: https://doi.org/10.1002/jps.2600520111>
22. Sov. Electrochem. 1965, 1, 60.
S. G., Barashkova N. V., Volkenshtein Y. B.:
23. Chem.-Tech. (Heidelberg) 1977, 6, 517.
M., Koberstein E.:
24. J. Am. Chem. Soc. 1970, 92, 6644.
< A. I., Temple D. R.: https://doi.org/10.1021/ja00725a048>
25. J. Org. Chem. 1975, 40, 3159.
A. I., Mihelich E. D.:
26. J. Org. Chem. 1975, 40, 2008.
< H. W., Haman A.: https://doi.org/10.1021/jo00901a036>
27. J. Org. Chem. 1977, 42, 2649.
< L. D., Vlattas I.: https://doi.org/10.1021/jo00435a033>
28. J. Chem. Soc., Perkin Trans. 1 1985, 173.
< A. J., Chadwick J.: https://doi.org/10.1039/p19850000173>
29. J. Med. Chem. 1984, 27, 570.
< C. B., Myers P. L., Butler R. C. M., Davis J. A., Doxey J. C., Higgins S. D., Myers M., Roach A. G., Smith C. F. C., Stillings M. R., Welbourn A. P.: https://doi.org/10.1021/jm00371a003>
30. J. Org. Chem. 1972, 37, 3224.
< J. R.: https://doi.org/10.1021/jo00986a007>
31. Tipper C. F. H. in: Electrode Kinetics: Principles and Methodology (R. G. Compton, Ed.). Elsevier Science Ltd., Amsterdam 1986.
32. Anal. Chem. 1964, 36, 706.
< R. S., Shain I.: https://doi.org/10.1021/ac60210a007>
33. J. Electroanal. Chem. 1995, 399, 147.
< J., Bernard C., Degrand C.: https://doi.org/10.1016/0022-0728(95)04197-4>
34. Electrochim. Acta 1995, 40, 2603.
< K., Hoskovcová I., Jirkovský J., Klíma J., Ludvík J.: https://doi.org/10.1016/0013-4686(95)00244-9>
35. J. Electroanal. Chem. 1999, 462, 181.
< J., Bernard C.: https://doi.org/10.1016/S0022-0728(98)00407-0>
36. Collect. Czech. Chem. Commun. 2000, 65, 941.
< J., Ludvík J.: https://doi.org/10.1135/cccc20000941>
37. Feoktistov L. C. in: Organic Electrochemistry (M. M. Baizer, Ed.). M. Dekker, New York 1983.
38. Justus Liebigs Ann. Chem. 1980, 1424.
< W., Oremek G., Ocakcioglu B.: https://doi.org/10.1002/jlac.198019800911>