A facile access to novel spiroxindole fused pyrrolidine and thiazolo pyrrolidine benzimidazole derivatives via 1,3-dipolar cycloaddition reaction

R1=H, 5-bromo, chloro; R2=H, methyl, ethyl, allyl; R3=4-chloro, bromo, fluoro, methyl, methoxy and 2-chloro, bromo. [Display omitted] A series of benzo[d]imidazol-2-yl)-1′-methyl-2-oxo-4′-phenylspiro[indoline-3,2′-pyrrolidine] and benzo[d]imidazol-2-yl)-2-oxo-7′-phenyl-3′,6′,7′,7a′-tetrahydro-1′H-sp...

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Bibliographic Details
Published in:Tetrahedron letters 2015-01, Vol.56 (5), p.721-726
Main Authors: Poomathi, Nataraj, Mayakrishnan, Sivakali, Muralidharan, D., Perumal, Paramasivan T.
Format: Article
Language:English
Subjects:
1,3-Dipolar cycloaddition
Amino acids
Benzimidazole
Cycloaddition
Derivatives
Diffraction
Heterocycles
Mass spectrometry
NMR spectroscopy
Pyrrolidines
Spiroxindoles
Tetrahedrons
X-rays
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Summary:R1=H, 5-bromo, chloro; R2=H, methyl, ethyl, allyl; R3=4-chloro, bromo, fluoro, methyl, methoxy and 2-chloro, bromo. [Display omitted] A series of benzo[d]imidazol-2-yl)-1′-methyl-2-oxo-4′-phenylspiro[indoline-3,2′-pyrrolidine] and benzo[d]imidazol-2-yl)-2-oxo-7′-phenyl-3′,6′,7′,7a′-tetrahydro-1′H-spiro[indoline-3,5′-pyrrolo[1,2-c]thiazole] carbonitrile were synthesized via 1,3-dipolar cycloaddition (1,3-DC) reaction. The azomethine ylides generated in situ from isatin/N-substituted isatin and secondary amino acids (sarcosine/S-proline) reacted with benzo-imidazol-2-yl-3-phenylacrylonitrile as a dipolarophile to give spiroxindole fused pyrrolidine and thiazolo pyrrolidine benzimidazole derivatives in good yields. The structure and stereochemistry of cycloadducts were confirmed by 1H and 13C NMR spectroscopy, mass spectrometry, and single crystal X-ray diffraction studies.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.12.088