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 |
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| Authors: | Mojtaba Lashkari Malek Taher Maghsoodlou Nourallah Hazeri Sayyed Mostafa Habibi‐Khorassani Niloufar Akbarzadeh Torbati Santiago García‐Granda Laura Torre‐Fernández |
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| Affiliation: | 1. Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, Zahedan, Iran;2. Department of Physical and Analytical Chemistry, University of Oviedo‐CINN, Oviedo, Spain |
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| Abstract: | A 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. |
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