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Diastereoselective Synthesis of Perfluoroalkylmethyl‐Substituted 1,2,3,4‐Tetrahydroquinolines Derivatives through 1‐Iodo‐1,3‐bis(acetoxy) Synthons

Abstract : Novel 2-perfluoroalkylmethyl,4-arylamino substituted tetrahydroquinolines (THQ) were expeditiously synthesized from perfluoroalkyl iodides RF–I and monosubstituted anilines. First, radical bis-addition of vinylacetate on RF–I afforded gem-iodoacetoxy derivatives (newly characterized by NMR and MS) being actually masked/activated aldol synthons. Their reaction in 1:4 ratio with arylamines afforded title THQ under mild conditions in good yields (60–95%) and diastereoselectivities (65:35 – 95:5 cis/trans isomer ratio); m-substituted anilines regiospecifically lead to 7-substituted THQ. Mechanistic investigation suggested the THQ formation to proceed through Michael then imine addition of two aniline units on an RF-substituted crotonaldehyde intermediate; then through the cyclization of the resulting bis(arylamino/imino) intermediate through electrophillic aromatic substitution. Various RF (C6, C2, C4) and arylamine substitutions (p-,o-,m- alkyl, alkoxyl, halogen…) were thus exemplified.
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https://hal.archives-ouvertes.fr/hal-03746659
Contributor : Laurent Boiteau Connect in order to contact the contributor
Submitted on : Friday, August 5, 2022 - 5:01:01 PM
Last modification on : Sunday, August 7, 2022 - 3:27:06 AM

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Salem El Kharrat, Philippe Laurent, Laurent Boiteau. Diastereoselective Synthesis of Perfluoroalkylmethyl‐Substituted 1,2,3,4‐Tetrahydroquinolines Derivatives through 1‐Iodo‐1,3‐bis(acetoxy) Synthons. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2022, 2022 (21), pp.e202200126. ⟨10.1002/ejoc.202200126⟩. ⟨hal-03746659⟩

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