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Reaction between alkyl isocyanides and dibenzoylacetylene in the presence of strong NH-acids: synthesis of highly functionalized aminofurans

✍ Scribed by Issa Yavari; Abdolali Alizadeh; Mohammad Anary-Abbasinejad; Hamid R Bijanzadeh

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
105 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

Protonation of the highly reactive 1:1 intermediates produced in the reaction between alkyl isocyanides and dibenzoylacetylene by saccharin, phthalimide, or 4-methyl-5-nitroimidazole, leads to vinylnitrilium cations, which undergo carbon-centered Michael type addition with the conjugate base of the NH-acid to produce highly functionalized aminofuran derivatives.

πŸ“œ SIMILAR VOLUMES

Reaction between heterocyclic NH-acids a
Reaction between heterocyclic NH-acids and dibenzoylacetylene in the presence of triphenylphosphine. Simple synthesis of 1-(3-furyl)-1H-imidazole derivatives
✍ Issa Yavari; Abdolali Alizadeh; Mohammad Anary-Abbasinejad πŸ“‚ Article πŸ“… 2002 πŸ› Elsevier Science 🌐 French βš– 168 KB

The reactive 1:1 intermediate obtained from the addition of triphenylphosphine to dibenzoylacetylene was trapped by heterocyclic NH-acids such as imidazole, 4-nitroimidazole, or 5-methyl-4-nitroimidazole to produce 2,3,5-trisubstituted furan derivatives. Using 2-benzoylimidazole or saccharin as NH-a