Cascade process for direct synthesis of indeno[1,2- b ]furans and indeno[1,2- b ]pyrroles from diketene and ninhydrin
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ORIGINAL ARTICLE
Cascade process for direct synthesis of indeno[1,2‑b]furans and indeno[1,2‑b]pyrroles from diketene and ninhydrin Atieh Rezvanian1 · Fatemeh Moradi1 · Vahideh Zadsirjan1 · Masoumeh Mohammadnejad1 · Majid M. Heravi1 Received: 8 August 2019 / Accepted: 23 September 2019 © Springer Nature Switzerland AG 2019
Abstract Novel and efficient multicomponent reactions (MCRs) involving diketene, ninhydrin (indane-1,2,3-trione) and one primary amine (3CR) or two different primary amines (4CR) were achieved for the successful synthesis of dihydro-4H-indeno[1,2b]furan-3-carboxamides or tetrahydroindeno[1,2-b]pyrrole-3-carboxamides, respectively. The merits of this method are highlighted by using either commercially available or easily accessible starting materials, operational simplicity, facile workup procedure, efficient usage of all the reactants, tolerance of a variety of functional groups and ability to conduct under un-catalyzed reaction condition. The products were also isolated by just decantation of the solvent, and for the purification column chromatography was non-required. Graphic abstract
Keywords Dihydro-4H-indeno[1,2-b]furan-3-carboxamides · Tetrahydroindeno[1,2-b]pyrrole-3-carboxamides · Diketene · Ninhydrin (indane-1,2,3-trione) · Primary amine Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11030-019-09996-7) contains supplementary material, which is available to authorized users. * Atieh Rezvanian [email protected] Extended author information available on the last page of the article
Introduction Furans, five-membered aromatic heterocycles, contain one oxygen atom which is usually found in diverse important compounds clouding naturally occurring compounds,
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medicines and polymers [1]. Besides, furans were used as synthetic intermediates to attain other valuable compounds [2–5]. Remarkably, the formation of this important structural framework has obtained considerable attention and an extensive range of methods were reported for the synthesis of furans and derivatives [6–8]. Indeno heterocycles frameworks are broadly found in various naturally occurring compounds and synthetic compounds having biological activities [9]. Particularly, furan and indeno-fused furan are valuable building blocks of intense biological potent molecules. For instance, the tricyclic indenofuran vocalizes the key substructures of GR-24 [10], (+)-strigol [11] and desmethylsorgolactone [12] (Fig. 1). These biological active compounds were used for the treatment of metabolic disorders. Also, due to the significance role of them in drug discovery, they were followed intensively in recent years [13]. Various methods have been reported for the synthesis of indenofurans. Yavari and co-workers in 2002 reported that the reaction of ninhydrin and dialkylacetylenedicarboxylates in the presence of P Ph3 produced C2-symmetric tetra-alkyl 2,5-dihydrofuro[2,3:2,3]indeno[2,1-b]furan-1,2,5,6-tetracarboxylates in high yields [1
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