Domino reactions between 3-(6-methylchromonyl)acrylonitrile and nucleophilic reagents
Magdy A. Ibrahim; Nasser M. El-Gohary;
Abstract
The chemical reactivity of electron deficient chromone–linked acrylonitrile [3-(6-methylchromonyl)acrylonitrile (1)] was studied towards some active methylene nitriles and active methylene ketones. Reaction of compound 1 with malononitrile, cyanoacetamide, ethyl cyanoacetate, malononitrile dimer and acetoacetanilide afforded 5-cyanomethylchromeno[4,3-b]pyridines 2–4 and 9. Compound 1 reacted with 1H-benzimidazol-2-ylacetonitrile producing pyrido[1,2-a]benzimidazole derivative 5. Benzonitrile derivatives 6–8 were efficiently synthesized from the reaction of compound 1 with acetylacetone, ethyl acetoacetate and diethylmalonate. In these reactions a diversity of products has been synthesized through a domino process, including Michael addition, retro-Michael with γ-pyrone ring opening followed by different types of recyclization (RORC). Structures of the new synthesized products were deduced on the basis of their analytical and spectral data, and the reaction mechanisms are discussed.
Other data
Title | Domino reactions between 3-(6-methylchromonyl)acrylonitrile and nucleophilic reagents | Authors | Magdy A. Ibrahim ; Nasser M. El-Gohary | Issue Date | 2018 | Publisher | Elsiever | Volume | 74 | Start page | 512 | End page | 518 |
Recommend this item
Similar Items from Core Recommender Database
Items in Ain Shams Scholar are protected by copyright, with all rights reserved, unless otherwise indicated.