期刊
HETEROCYCLES
卷 104, 期 3, 页码 481-493出版社
Japan Inst Heterocyclic Chemistry
DOI: 10.3987/COM-21-14588
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The chemical reactivity of 1H-benzimidazol-2-ylacetonitrile and dimedone towards some simple condensates was investigated. The results showed that the nucleophilic addition reaction mainly occurred at the olefinic carbon with concomitant cycloaddition or cyclocondensation.
The chemical reactivity of 1H-benzimidazol-2-ylacetonitrile and dimedone was investigated towards some simple condensates (1a-d and 2a-c) obtained from condensation reaction of 3-formylchromone with some active methylene compounds. Mainly, the used nucleophiles undergo nucleophilic addition at the olefinic carbon with concomitant cycloaddition or cyclocondensation. Chromonylacrylonitrile 1a reacted with 1H-benzimidazol-2-ylacetonitrile through gamma-pyrone ring opening followed by cyclocondensation giving pyrido[1,2-a]benzimidazole derivative 5. The simple condensates 2b and 2c showed similar behavior towards 1H-benzimidazol-2-ylacetonitrile and dimedone leading to the same products which are identical with those obtained from 3-formylchromone with the same reagents. Structures of the new synthesized products were established based on elemental analysis and spectral data.
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