Formation of epoxychromeno[4,3- c ]isoquinolines through diastereoselective one-pot IMDA reaction of 4-chloro-3-[(1 E )-
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ORIGINAL PAPER
Formation of epoxychromeno[4,3‑c]isoquinolines through diastereoselective one‑pot IMDA reaction of 4‑chloro‑3‑[(1E)‑3‑oxo‑3‑phenyl‑1‑propen‑1‑yl]‑2H‑chromen‑2‑one and furfurylamine Abdolali Alizadeh1 · Kaveh Amir Ashjei Asalemi1 · Behnaz Farajpour1 · Mohammad Reza Halvagar2 Received: 7 May 2020 / Accepted: 7 July 2020 © Iranian Chemical Society 2020
Abstract An intramolecular Diels–Alder mediated reaction of (2E)-3-(4-chloro-2-methylene-2H-chromen-3-yl)-1-phenyl-2-propen1-one, which was obtained in situ from the reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehyde and Wittig reagent, with furfurylamine leads to fused epoxychromeno[4,3-c]isoquinolines. Reaction performed in one-pot condition and only one diastereomer was obtained. In this method, the key step for the formation of the final product is IMDA reaction. Graphic abstract A series of fused epoxychromeno[4,3-c]isoquinoline compounds containing chromene skeleton have been synthesized through the cyclization strategy, from 4-chloro-2-oxo-2H-chromene-3-carbaldehyde, Wittig reagent, and furfurylamine. The reactions were carried out under reflux condition in DCM/toluene.
Keywords 4-Chloro-2-oxo-2H-chromene-3-carbaldehyde · Wittig reagent · (2E)-3-(4-chloro-2-methylene-2H-chromen3-yl)-1-phenyl-2-propen-1-one · Furfurylamine · IMDA reaction · Coumarin-based heterocycles · One-pot process · Diastereoselective
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13738-020-01999-8) contains supplementary material, which is available to authorized users. * Abdolali Alizadeh [email protected]; [email protected] Extended author information available on the last page of the article
Introduction Coumarins are one of the most common and valuable naturally occurring structures in chemistry and biological chemistry [1–3]. These structures are widely found in plants and many of them extracted successfully and applied
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in biological and pharmaceutical purposes [4]. Investigations showed that coumarin-based heterocycles exhibit different biological activities compared to simple coumarin derivatives so adding a heterocycle moiety to coumarin structure either as linking group or as a fused part of whole structure could be a powerful and general tool to synthesize new range of coumarins for evaluation of their biological activities [5, 6]. A survey in the literature revealed that scientists tried different methods to synthesize new coumarin heterocyclic derivatives. For instance, Yang and co-workers applied a four-component Ugi reaction to achieve this goal. They used coumarin-3-carboxylic, isocyanides, anilines, and different aldehydes to obtain chromeno[3,4-c]pyrrole-3,4-diones [7]. Another application of multicomponent reaction in the synthesis of coumarin-based heterocycles was reported by Shi et al. [8]. The final 3-pyrrolyl coumarin was obtained through the four-component reaction between arylglyoxal, dialkyl acetylenedicarboxylates, amines, and 4-hydroxycoumarin. Besid
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