A novel four-component reaction of diethylamine, an aromatic aldehyde and an alkyl isocyanide with dialkyl acetylenedicarboxylates in the presence of silica gel: an efficient route for the regio- and stereoselective synthesis of sterically congested alkenes |
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Authors: | Ebrahim Ahmadi Ali Ramazani Mehdi Nekomanesh Haghighi |
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Institution: | a Department of Chemistry, the University of Zanjan, PO Box 45195-313, Zanjan, Iran b Department of Polymerization Engineering, Iran Polymer and Petrochemical Institute (IPPI), PO Box 14965-115, Tehran, Iran |
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Abstract: | The 1:1 intermediate generated by the addition of an isocyanide to a dialkyl acetylenedicarboxylate is trapped by the iminium ion intermediate that forms from the reaction between an aromatic aldehyde and diethylamine. The reactions were completed in the presence of silica gel powder. The product dialkyl 2-(alkylamino)carbonyl]-3-(Z)-1-(diethylamino)-1-arylmethylidene]succinates, were produced in acceptable yields. The reactions are completely regio- and stereoselective. |
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Keywords: | Silica gel Multicomponent reaction Isocyanide Aldehyde Acetylenic ester |
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