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A novel route for the diastereoselective synthesis of dispiro[tetrahydroquinoline-bis(2,2-dimethyl[1,3]dioxane-4,6-dione)] derivatives via a one-pot domino multicomponent reaction of arylamines, aromatic aldehydes, and meldrum's acid

AuthorsLashkari, Mojtaba; Maghsoodlou, Malek Taher; Hazeri, Nourallah; García-Granda, Santiago CSIC ORCID; Torre-Fernández, Laura
Issue Date2015
PublisherJohn Wiley & Sons
CitationJournal of Heterocyclic Chemistry 52(3): 873-879 (2015)
AbstractA protocol has been developed for the diastereoselective synthesis of dispiro[tetrahydroquinoline-bis(2,2-dimethyl[1,3] dioxane-4,6-dione)] derivatives via a one-pot domino multicomponent reaction of arylamines, aromatic aldehydes, and Meldrum's acid for the first time. The products, with remarkable diastereoselectivity, were successfully synthesized in acetic acid media in ambient temperature along with the suggested mechanism through combination of domino Knoevenagel, Michael, and Diels–Alder reactions. The products have been characterized by IR, mass, 1H NMR, 13C NMR spectroscopy, and elemental analyses. The stereoselectivity of compounds was established with crystallography and NMR spectroscopy.
Identifiersdoi: 10.1002/jhet.1984
issn: 0022-152X
e-issn: 1943-5193
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