Stereospecific Synthesis of (Z)-1,3-Oxazolobenzimidazoles from Imidazole- and Benzene-Ring-Substituted Benzimidazoles and α,β-Acetylenic γ-Hydroxynitriles
Publication type: Journal Article
Publication date: 2010-07-07
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
A stereospecific, facile synthesis of (Z)-1,3-oxazolobenzimidazoles from imidazole- and benzene-ring-substituted benzimidazoles and α,β-acetylenic γ-hydroxynitriles has been elaborated. The reaction proceeds smoothly in acetonitrile without catalyst (room temperature, 3-5 days or 35-40 °C, 20-72 h) to afford the target compounds in 33-90% yields. The annulation involves an intermediate vinyl carbanion with zwitterionic character, which, after transformation into an O-centered zwitterion, is further inserted into the aromatic system of the imidazole ring. The synthesis contributes to the basic benzimidazole and acetylene chemistry and drug design.
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Trofimov B. et al. Stereospecific Synthesis of (Z)-1,3-Oxazolobenzimidazoles from Imidazole- and Benzene-Ring-Substituted Benzimidazoles and α,β-Acetylenic γ-Hydroxynitriles // Synthesis. 2010. Vol. 2010. No. 16. pp. 2828-2840.
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Trofimov B., Andriyankova L., Belyaeva K., Nikitina L., Afonin A., Trofimov B. A. Stereospecific Synthesis of (Z)-1,3-Oxazolobenzimidazoles from Imidazole- and Benzene-Ring-Substituted Benzimidazoles and α,β-Acetylenic γ-Hydroxynitriles // Synthesis. 2010. Vol. 2010. No. 16. pp. 2828-2840.
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TY - JOUR
DO - 10.1055/s-0030-1258152
UR - https://doi.org/10.1055/s-0030-1258152
TI - Stereospecific Synthesis of (Z)-1,3-Oxazolobenzimidazoles from Imidazole- and Benzene-Ring-Substituted Benzimidazoles and α,β-Acetylenic γ-Hydroxynitriles
T2 - Synthesis
AU - Trofimov, Boris
AU - Andriyankova, Ludmila
AU - Belyaeva, Kseniya
AU - Nikitina, Lina
AU - Afonin, A.V.
AU - Trofimov, B. A.
PY - 2010
DA - 2010/07/07
PB - Georg Thieme Verlag KG
SP - 2828-2840
IS - 16
VL - 2010
SN - 0039-7881
SN - 1437-210X
ER -
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@article{2010_Trofimov,
author = {Boris Trofimov and Ludmila Andriyankova and Kseniya Belyaeva and Lina Nikitina and A.V. Afonin and B. A. Trofimov},
title = {Stereospecific Synthesis of (Z)-1,3-Oxazolobenzimidazoles from Imidazole- and Benzene-Ring-Substituted Benzimidazoles and α,β-Acetylenic γ-Hydroxynitriles},
journal = {Synthesis},
year = {2010},
volume = {2010},
publisher = {Georg Thieme Verlag KG},
month = {jul},
url = {https://doi.org/10.1055/s-0030-1258152},
number = {16},
pages = {2828--2840},
doi = {10.1055/s-0030-1258152}
}
Cite this
MLA
Copy
Trofimov, Boris, et al. “Stereospecific Synthesis of (Z)-1,3-Oxazolobenzimidazoles from Imidazole- and Benzene-Ring-Substituted Benzimidazoles and α,β-Acetylenic γ-Hydroxynitriles.” Synthesis, vol. 2010, no. 16, Jul. 2010, pp. 2828-2840. https://doi.org/10.1055/s-0030-1258152.
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