A three-component cyclocondensation of 4-(dimethylamino)benzaldehyde, 2-phenacyl-1H-benz-imidazoles, and methyl 3-aminobut-2-enoate in refluxing acetic acid occurs via a Hantzsch type reaction and is accompanied by the loss of N,N-dimethylaniline to give the previously unknown methyl 6-aryl-5-(1H-benzimidazol-2-yl)-2-methylnicotinates.
Similar content being viewed by others
References
I. B. Dzvinchuk and M. O. Lozinskii, in: V. G. Kartsev (editor), Selected Methods for the Synthesis and Modification of Heterocycles. Quinolines: Chemical and Biological Activity [in Russian], Vol. 6, ICSPF Press, Moscow (2007), p. 64.
I. B. Dzvinchuk, A. N. Chernega, and M. O. Lozinskii, Khim. Geterotsikl. Soedin., 1792 (2007). [Chem. Heterocycl. Comp., 43, 1519 (2007)].
I. B. Dzvinchuk and N. A. Tolmachova, Khim. Geterotsikl. Soedin., 554 (2001). [Chem. Heterocycl. Comp., 37, 506 (2001)].
I. B. Dzvinchuk, Khim. Geterotsikl. Soedin., 578 (2007). [Chem. Heterocycl. Comp., 43, 474 (2007)].
I. B. Dzvinchuk and M. O. Lozinskii, Khim. Geterotsikl. Soedin., 585 (2007). [Chem. Heterocycl. Comp., 43, 480 (2007)].
I. B. Dzvinchuk, A. V. Vypirailenko, M. O. Lozinskii, and T. V. Makitruk, Ukr. Khim. Zhurn., 65, No 10, 111 (1999).
A. J. Gordon and R. A. Ford, The Chemist’s Companion [Russian translation], Mir, Moscow (1976), pp. 217, 282.
A. F. Pozharskii, Theoretical Basis of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985), p. 126.
I. B. Dzvinchuk and M. O. Lozinskii, Khim. Geterotsikl. Soedin., 1637 (2007), [Chem. Heterocycl. Comp., 43, 1390 (2007)].
H. E. Gottlieb, V. Kotlyar, and A. Nudelman, J. Org. Chem., 62, 7512 (1997).
I. B. Dzvinchuk, A. M. Nesterenko, and M. O. Lozinskii, Khim. Geterotsikl. Soedin., 252 (2008). [Chem. Heterocycl. Comp., 44, 190 (2008)].
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1186–1192, August, 2009.
Rights and permissions
About this article
Cite this article
Dzvinchuk, I.B., Lozinskii, M.O. Synthesis of methyl 6-aryl-5-(1H-benzimidazol-2-yl)-2-methylnicotinates. Chem Heterocycl Comp 45, 942–947 (2009). https://doi.org/10.1007/s10593-009-0370-z
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-009-0370-z