5‐Amido‐ and 5‐Amino‐Substituted Epoxyisoindolo[2,1‐a]tetrahydroquinolines and 10‐Carboxylic Acids: Their Synthesis and Reactivity |
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| Authors: | Vladimir P Zaytsev Fedor I Zubkov Flavien A A Toze Daria N Orlova Maria N Eliseeva Dmitry G Grudinin Eugeniya V Nikitina Alexey V Varlamov |
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| Institution: | 1. Department of Organic Chemistry, Peoples' Friendship University of Russia, , Moscow 117198, Russian Federation;2. Department of Chemistry, University of Douala, Faculty of Sciences, , PO Box 24157 Douala, Cameroon;3. Valeant Canada Ltd., , Montréal, Québec H4M 1V1, Canada |
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| Abstract: | The interactions between 4‐R‐substituted 2‐furyl‐1,2,3,4‐tetrahydroquinolines (synthesized by the Povarov reaction) and a number of alkenes have been investigated. Maleic, dibromomaleic, dichloromaleic, and citraconic anhydrides, as well as acryloyl, methacryloyl, crotonyl, and cynnamoyl chlorides were used as alkene components. It was shown that the initial N‐acylation of the tetrahydroquinolines was followed by a spontaneous 4+2]‐cycloaddition of an N‐acryloyl substituent to the furan ring. It was established that the intramolecular Diels–Alder reaction of furans is reversible, occurs stereoselectively as exo‐addition, and led to target epoxyisoindolo2,1‐a]tetrahydroquinolines with moderate yields. Oxidation and aromatization of the synthesized products were carried out. |
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