Synthesis and study of 1-aryl-1H-4,5-dihydroimidazoles

Synthesis

Volumn , Issue 6, 2004, Pages 851-856

  Perillo, Isabel ^a   Caterina, M Cristina ^a   López, Julieta ^a   Salerno, Alejandra ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Alkylations; Cyclization; Heterocycles; Nitrogen; Reductions

Indexed keywords

AROMATIC COMPOUNDS; CONDENSATE RETURN LINES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CYCLOCONDENSATION; FORMYLATION;

NITROGEN COMPOUNDS;

4 NITROPHENOL; ETHYLENEDIAMINE DERIVATIVE; FORMIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; METHYL IODIDE; POLYPHOSPHATE; SODIUM DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; POLYMERIZATION; PRECURSOR; REDUCTION; SYNTHESIS;

EID: 2342570828     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-816011     Document Type: Article

References (38)

1. Faust, J. A.; Yee, L. S.; Sahyun, M. J. Org. Chem. 1961, 26, 4044.
2. (a) Ishikawa, F. Chem. Pharm. Bull. 1980, 28, 1394.
3. (b) McFarland, J. W.; Conover, L. M.; Howes, H. L.; Lynch, J. E.; Chisholm, D. R.; Austin, W. C.; Cornwell, R. L.; Danilewicz, J. C.; Courtney, W.; Morgan, D. H. J. Med. Chem. 1969, 12, 1066.
4. Tanabe Seiyaku Co., Ltd., Jpn. Kokai Tokkyo Koho JP 60 51176, 1985; Chem. Abstr. 1985, 103, 141951.
5. Le Bian, G.; Rondu, F.; Pelé-Tounian, A.; Wang, X.; Lidy, S.; Toubout, E.; Lamouri, A.; Dive, G.; Huet, J.; Pfeiffer, B.; Renard, P.; Guardiola-Lemaitre, B.; Manéchez, D.; Penicaud, L.; Ktorza, A.; Godfroid, J.-J. J. Med. Chem. 1999, 42, 1587; and references cited therein.
6. Szabo, B. Pharmacol. Ther. 2002, 93, 1; and references cited therein.
7. Dehydrogenation to imidazoles. Among others: (a) Martin, P. K.; Matthews, H. R.; Rapaport, H.; Thyagarajan, G. J. Org. Chem. 1968, 33, 3758. (b) Hughey, J. L.; Knapp, S.; Schugar, H. Synthesis 1980, 489. (c) Klem, R. E.; Skinner, H. F.; Walba, H.; Isensee, R. H. J. Heterocycl. Chem. 1970, 7, 403. (d) Matsuura, T.; Ito, Y.; Saito, I. Bull. Chem. Soc. Jpn. 1973, 46, 3805.
8. Dehydrogenation to imidazoles. Among others: (a) Martin, P. K.; Matthews, H. R.; Rapaport, H.; Thyagarajan, G. J. Org. Chem. 1968, 33, 3758. (b) Hughey, J. L.; Knapp, S.; Schugar, H. Synthesis 1980, 489. (c) Klem, R. E.; Skinner, H. F.; Walba, H.; Isensee, R. H. J. Heterocycl. Chem. 1970, 7, 403. (d) Matsuura, T.; Ito, Y.; Saito, I. Bull. Chem. Soc. Jpn. 1973, 46, 3805.
9. Dehydrogenation to imidazoles. Among others: (a) Martin, P. K.; Matthews, H. R.; Rapaport, H.; Thyagarajan, G. J. Org. Chem. 1968, 33, 3758. (b) Hughey, J. L.; Knapp, S.; Schugar, H. Synthesis 1980, 489. (c) Klem, R. E.; Skinner, H. F.; Walba, H.; Isensee, R. H. J. Heterocycl. Chem. 1970, 7, 403. (d) Matsuura, T.; Ito, Y.; Saito, I. Bull. Chem. Soc. Jpn. 1973, 46, 3805.
10. Dehydrogenation to imidazoles. Among others: (a) Martin, P. K.; Matthews, H. R.; Rapaport, H.; Thyagarajan, G. J. Org. Chem. 1968, 33, 3758. (b) Hughey, J. L.; Knapp, S.; Schugar, H. Synthesis 1980, 489. (c) Klem, R. E.; Skinner, H. F.; Walba, H.; Isensee, R. H. J. Heterocycl. Chem. 1970, 7, 403. (d) Matsuura, T.; Ito, Y.; Saito, I. Bull. Chem. Soc. Jpn. 1973, 46, 3805.
11. Jones, R. C. F.; Howard, K. J.; Snaith, J. S. Tetrahedron Lett. 1997, 38, 1647.
12. Salerno, A.; Ceriani, V.; Perillo, I. A. J. Heterocycl. Chem. 1992, 29, 1725; and references cited therein.
13. Salerno, A.; Ceriani, V.; Perillo, I. A. J. Heterocycl. Chem. 1997, 34, 709; and references cited therein.
14. Fernández, B. M.; Reverdito, A. M.; Paolucci, G. A.; Perillo, I. A. J. Heterocycl. Chem. 1987, 24, 1717.
15. Anderson, H. W.; Jones, R. C. F.; Saunders, J. J. Chem. Soc., Perkin Trans. 1 1986, 1995; and references cited therein.
16. Pandit, U. K. Pure Appl. Chem. 1994, 66, 759; and references cited therein.
17. (a) Seefelder, M.; Jentzsch, W. Badische Anilin & Soda-Fabrik A.-G., German Patent 1 189998, 1965; Chem. Abstr. 1965, 63, 610.
18. (b) Jentzsch, W.; Seefelder, M. Chem. Ber. 1965, 98, 1342.
19. Bieraugel, H.; Plemp, R.; Hiemstra, H. C.; Pandit, U. K. Tetrahedron 1983, 39, 3971.
20. Vecerková, J.; Vecerek, B.; Chundela, B. Chem. Listy 1953, 47, 1680; Chem. Abstr. 1955, 49, 1019.
21. Vecerková, J.; Vecerek, B.; Chundela, B. Chem. Listy 1953, 47, 1680; Chem. Abstr. 1955, 49, 1019.
22. (a) Grundmann, C.; Kreutzberger, A. J. Am. Chem. Soc. 1955, 77, 6559.
23. (b) Grundmann, C.; Kreutzberger, A. US Patent 2841585, 1958; Chem. Abstr. 1958, 52, 20211.
24. Docker, T.; Frank, A.; Krug, H. Ger. Offen. 2728976, 1979; Chem. Abstr. 1979, 90, 121603.
25. Becke, F.; Paessler, P.; Swoboda, O. P. Ger. Offen. 1922802, 1970; Chem. Abstr. 1971, 74, 22840.
26. Hagen, H.; Becke, F. Ger. Offen. 2040502, 1970; Chem. Abstr. 1972, 76, 140862.
27. (a) Poindexter, G. S.; Owens, D. A.; Dolan, P. L.; Woo, E. J. Org. Chem. 1992, 57, 6257; and references cited therein.
28. (b) Fourneau, J.-P.; Lestrange, M. Y. Bull. Soc. Chim. Fr. 1947, 827.
29. Chung, T. F.; Wu, Y. M.; Cheng, C. H. J. Org. Chem. 1984, 49, 1215.
30. Hedrera, M. E.; Perillo, I. A. Trends HeterocycL Chem. 2002, 8, 105.
31. García, M. B.; Orelli, L. R.; Magri, M. L.; Perillo, I. A. Synthesis 2002, 2687.
32. 25 and usually both species can be spectroscopically identified.
33. Göblyös, A.; Lázár, L.; Evanics, F.; Fülöp, F. Heterocycles 1999, 51, 2431; and references cited therein.
34. Yokohama, M.; Yoshida, S.; Imamoto, T. Synthesis 1982, 591.
35. Pollmann, W.; Schramm, G. Biochim. Biophys. Acta 1964, 80, 1.
36. Salerno, A.; Caterina, C.; Perillo, I. A. Synth. Commun. 2000, 30, 3369.
37. Wright, W. B. Jr.; Brabander, H. J. J. Org. Chem. 1961, 26, 2120.
38. Perillo, I. A.; Lamdan, S. J. Chem. Soc., Perkin Trans. 1 1975, 894.