N-Alkylation of benzimidazoles with ketonic Mannich bases and the reduction of the resulting 1-(3-oxopropyl)benzimidazoles

• Authors: Gheorghe Roman
• Languages of publication: EN

Abstracts

EN

Benzimidazole, benzimidazoles diversely substituted at position 2, and 5,6-dimethylbenzimidazole have been alkylated at N 1 with ketonic Mannich bases derived from acetophenones, acetylnaphthalenes, 2-acetylthiophene and 1-tetralone to afford a series of novel 1-(3-oxopropyl)benzimidazoles. The reduction of these transamination products with NaBH4 in methanol produced the corresponding 1-(3-hydroxypropyl)benzimidazoles in excellent yields. [...]

Keywords

EN

Benzimidazole; Mannich bases; N-alkylation; Reduction

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2012
• Volume: 10
• Issue: 5
• Pages: 1516-1526

Dates

published

1 - 10 - 2012

online

21 - 7 - 2012

Contributors

author

Gheorghe Roman

• Petru Poni Institute of Macromolecular Chemistry, Iaşi, 700487, Romania

References

• [1] G. Roman, Rev. Chim. (Bucharest) 63, 255 (2012)
• [2] M. Tramontini, Synthesis 703 (1973)
• [3] M. Tramontini, L. Angiolini, Tetrahedron 46, 1791 (1990) http://dx.doi.org/10.1016/S0040-4020(01)89752-0[Crossref]
• [4] F. Andreani, R. Andrisano, C. Della Casa, M. Tramontini, J. Chem. Soc. [C] 1157 (1970)
• [5] R. Zelnik, F. Strehlau, Experientia 21, 617 (1965) http://dx.doi.org/10.1007/BF02144035[Crossref]
• [6] R. Zelnik, F. Strehlau, Mem. Inst. Butantan 35, 147 (1971); Chem. Abstr. 77, 126499c (1972)
• [7] C. Fauran, J. Eberle, A.Y. Le Cloarec, G. Raynaud, M. Sergant, French Patent 2,186,251 (1974); Chem. Abstr. 81, 3938v (1974)
• [8] C. Fauran, J. Eberle, G. Raynaud, N. Dorme, German Patent 2,431,532 (1975); Chem. Abstr. 82, 156314j (1975)
• [9] G. Roman, E. Comaniţă, B. Comaniţă, Khim. Geterotsikl. Soedin. 1228 (2002); G. Roman, E. Comaniţă, B. Comaniţă, Chem. Heterocycl. Compd. 38, 1072 (2002)
• [10] G. Roman, Compt. Rend. Acad. Bulg. Sci. 58, 397 (2005)
• [11] G. Roman, E. Comaniţă, B. Comaniţă, Tetrahedron 58, 1617 (2002) http://dx.doi.org/10.1016/S0040-4020(02)00027-3[Crossref]
• [12] M.A.P. Martins, G.F. Fiss, C.P. Frizzo, F.A. Rosa, H.G. Bonacorso, N. Zanatta, J. Braz. Chem. Soc. 21, 240 (2010) http://dx.doi.org/10.1590/S0103-50532010000200008[Crossref]
• [13] M. Boiani, M. González, Mini-Rev. Med. Chem. 5, 409 (2005) http://dx.doi.org/10.2174/1389557053544047[Crossref]
• [14] B. Narasimhan, D. Sharma, P. Kumar, Med. Chem. Res. 21, 269 (2012) http://dx.doi.org/10.1007/s00044-010-9533-9[Crossref]
• [15] (a) K. Ramaiah, J.S. Grossert, D.L. Hooper, P.K. Dubey, J. Ramanatham, J. Indian Chem. Soc. 76, 140 (1999)
• [16] (b) M.A. Phillips, J. Chem. Soc. 2393 (1928) [Crossref]
• [17] B.N. Feitelson, R. Rothstein, J. Chem. Soc. 2426 (1958)
• [18] M. Murray, Biochem. Pharmacol. 36, 463 (1987) http://dx.doi.org/10.1016/0006-2952(87)90352-2[Crossref]
• [19] I. Gackowska, J. Sawlewicz, M. Janowiec, Acta Pol. Pharm. 44, 491 (1987)
• [20] C.E. Maxwell, Org. Synth. Coll. 3, 305 (1958)
• [21] F. Lehman, Å. Pilotti, K. Luthman, Mol. Divers. 7, 145 (2003) http://dx.doi.org/10.1023/B:MODI.0000006809.48284.ed[Crossref]
• [22] D. Sielemann, R. Keuper, N. Risch, J. prakt. Chem. 341, 487 (1999) http://dx.doi.org/10.1002/(SICI)1521-3897(199907)341:5<487::AID-PRAC487>3.0.CO;2-J[Crossref]
• [23] N. Mann, W. Back, E. Mutschler, Arch. Pharm. (Weinheim) 306, 625 (1973)
• [24] S.W. Pelletier, J. Org. Chem. 17, 313 (1952) http://dx.doi.org/10.1021/jo01136a020[Crossref]
• [25] G.R. Brown, A.M. Bamford, J. Bowyer, D.S. James, N. Rankine, E. Tang, V. Torr, E.J. Culbert, Bioorg. Med. Chem. Lett. 10, 575 (2000) http://dx.doi.org/10.1016/S0960-894X(00)00051-2[Crossref]
• [26] E.B. Knott, J. Chem. Soc. 1190 (1947) [Crossref]
• [27] E.D. Taylor, W.L. Nobles, J. Am. Pharm. Assoc., Sci. Ed. 49, 317 (1960) http://dx.doi.org/10.1002/jps.3030490517[Crossref]
• [28] E. Comaniţă, I. Popovici, B. Comaniţă, G. Roman, ACH-Models Chem. 134, 3 (1997)
• [29] Y.-W. Ho, C.-T. Yao, J. Chin. Chem. Soc. 50, 283 (2003) [Crossref]
• [30] W.M. Welch, C.A. Harbert, R. Sarges, W.P. Stratten, A. Weissman, J. Med. Chem. 20, 699 (1977) http://dx.doi.org/10.1021/jm00215a016[Crossref]
• [31] P. Horstmann, B. Unterhalt, Arch. Pharm. Pharm. Med. Chem. 330, 362 (1997) http://dx.doi.org/10.1002/ardp.19973301109[Crossref]
• [32] U. Westerwelle, A. Esser, N. Risch, Chem. Ber. 124, 571 (1991) http://dx.doi.org/10.1002/cber.19911240324[Crossref]

Identifiers

DOI

10.2478/s11532-012-0062-x