Switching the reactivity of cyanomethylpyridinium salts in the 1,3-cycloaddition conditions with alkyl propiolates to cyanoindolizines or cyanoazaindolizinyl-indolizines - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Tetrahedron Année : 2020

Switching the reactivity of cyanomethylpyridinium salts in the 1,3-cycloaddition conditions with alkyl propiolates to cyanoindolizines or cyanoazaindolizinyl-indolizines

Résumé

A particular reactivity of 1-cyanomethylpyridinium salts was revealed in the [3 + 2] cycloaddition conditions with alkyl propiolates. Cycloadducts 3 were obtained in reactions carried out at room temperature while refluxing in CH3CN provided unexpected ethyl or methyl 3-(3-cyanoimidazo[1,2-a]pyridin-2-yl)indolizine-1-carboxylates 4. The structure of the new 2:1 azaindolizine-indolizine adducts was secured by X-ray analysis. Methodological efforts have enabled the adjustment of the reactivity towards the formation of 3-cyanoindolizines 3 or cyanoazaindolizine-indolizines 4. A mechanism for the formation of azaindolizine-indolizines was proposed. A portfolio of rare cyanoindolizines and cyanoazaindolizine-indolizines has been successfully obtained.

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Chimie
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hal-03491427 , version 1 (17-10-2022)

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Iuliana-Monica Moise, Alina Ghinet, Sergiu Shova, Elena Bîcu. Switching the reactivity of cyanomethylpyridinium salts in the 1,3-cycloaddition conditions with alkyl propiolates to cyanoindolizines or cyanoazaindolizinyl-indolizines. Tetrahedron, 2020, 76, pp.131502 -. ⟨10.1016/j.tet.2020.131502⟩. ⟨hal-03491427⟩
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