A new method of synthesizing deoxybenzoins from 1,3-dimethyl-2-(α- benzyloxybenzyl)imidazolium and 1,3-dimethyl-2-(α- benzyloxybenzyl)benzimidazolium iodides based on Wittig-type rearrangement

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 8, 1997, Pages 1235-1242

  Miyashita, Akira ^a   Matsuoka, Yoshiyuki ^a   Suzuki, Yumiko ^a   Iwamoto, Ken Ichi ^a   Higashino, Takeo ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

1,3 dimethyl 2 ( benzyloxybenzyl)benzimidazolium salt; Azolium salt; Azolium ylide; Deoxybenzoin; Metal carbonate; Wittig rearrangement

Indexed keywords

BENZOIN; CARBONIC ACID; IMIDAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0030764328     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.1235     Document Type: Article

References (33)

1. Miyashita A., Matsuoka Y., Iwamoto K., Higashino T., Chem. Pharm. Bull., 42, 1960-1962 (1994).
2. a) Ugai T., Tanaka R., Dokawa S., Yakugaku Zasshi, 63, 296-300 (1943);
3. b) Ide W. S., Buck J. S., Org. React., 4, 269-304 (1948);
4. c) Castells J., Pujol F., Llitjos H., Moreno-Manas M., Tetrahedron, 38, 337-346 (1982);
5. d) Miyashita A., Matsuda H., Iijima C., Higashino T., Chem. Pharm. Bull., 38, 1147-1152 (1990);
6. e) Miyashita A., Matsuda H., Higashino T., Chem. Pharm. Bull., 40, 2627-2631 (1992).
7. a) Wittig G., Doser H., Lorenz I., Justus Liebigs Ann. Chem., 562, 192-205 (1949);
8. b) Wittig G., Davis P., Koenig G., Chem. Ber., 84, 627 (1951);
9. c) Wittig G., Stahnecker E., Justus Liebigs Ann. Chem., 605, 69-93 (1957).
10. a) Stevens T. S., Creighton E. M., Gordon A. B., MacNicol M., J. Chem. Soc., 1928, 3193-3197;
11. b) Stevens T. S., Snedden W. W., Stiller E. T., Thomson T., J. Chem. Soc., 1930, 2119-2125;
12. c) Dunn J. L., Stevens T. S., J. Chem. Soc., 1932, 1926-1931;
13. d) Pine S. H., Org. React., 18, 403-464 (1970).
14. a) Sommelet M., C. R. Acad. Sci., 205, 56-58 (1937);
15. b) Hauser C. R., Kantor S. W., J. Am. Chem. Soc., 73, 1437-1441 (1951);
16. c) Kantor S. W., Hauser C. R., J. Am. Chem. Soc., 73, 4122-4131 (1951);
17. d) Hauser C. R., Manyik R. M., Brasen W. R., Bayless P. L., J. Org. Chem., 20, 1119-1128 (1955).
18. Cast J., Stevens T. S., Holmes J., J. Chem. Soc., 1960, 3521-3527.
19. a) Baker W., Chadderton J., Harborne J. B., Ollis W. D., J. Chem. Soc., 1953, 1852-1860;
20. b) Baker W., Harborne J. B., Ollis W. D., ibid., 1953, 1860-1864;
21. c) Vishnu C., Sant P., J. Indian Chem. Soc., 54, 542-544 (1977);
22. d) Rajadhyaksha V. J., Schroer R. A., Brock P. J., Krueger E. R., U.S. Patent 4 038 415 [Chem. Abstr., 87, 167733z (1977)].
23. Allen C. F. H., Barker W. E., Org. Synth. Coll. Vol., 2, 156-158 (1948).
24. Lansbury P. T., Pattison V. A., J. Am. Chem. Soc., 84, 4295-4298 (1962).
25. Schollkopf U., Angew. Chem., 82, 795-805 (1970).
26. Miyashita A., Kurachi A., Matsuoka Y., Tanabe N., Suzuki Y., Iwamoto K., Higashino T., Heterocycles, 44, 417-426 (1997).
27. a) Beilstein EII (7), p. 368;
28. b) ibid., H (7), p. 436;
29. c) ibid., H (7), p. 438;
30. d) ibid., EII (8), p. 192;
31. e) ibid., H (7), p. 454;
32. f) ibid., H (7), p. 447.
33. 2-Benzoyl-1,3-dimethylbenzimidazolium iodide (14) was prepared from 1-methylbenzimidazole through lithiation, addition of benzonitrile, hydrolysis, and quaternization. The details will be reported elsewhere.