Diastereoselective synthesis of multisubstituted isoindolines via Sequential Ugi and aza-Michael addition reaction |
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| Institution: | 1. Department of Chemistry, Lomonosov Moscow State University, Moscow 119991, Russia;2. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic Uzbekistan, Uzbekistan;3. National Research Center “Kurchatov Institute”, Moscow, Russia;4. Peoples'' Friendship University of Russia (RUDN), Moscow, Russia;5. Nesmeyanov Institute of Organoelement Compounds of RAS, Moscow, Russia;1. Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079, PR China;2. Institute of Medicinal Chemistry, Hubei University of Medicine, Shiyan 442000, PR China;1. Faculty of Chemistry, Shahid Beheshti University, G.C., P.O. Box 19396-4716, Tehran, Iran;2. Рeoples’ Friendship University of Russia (RUDN University), 6, Miklukho-Maklaya Street, Moscow, 117198, Russian Federation;1. Laboratory of Synthetic and Biomolecular Chemistry, Faculty of Chemistry, University of Havana, Zapata y G, Havana 10400, Cuba;2. Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany |
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| Abstract: | A new efficient and diastereoselective synthesis of multisubstituted isoindolines with two stereogenic centers via sequential Ugi/aza-Michael addition reaction was developed. Ugi-3CR of aldehydes 1, amines 2 and isocyanates 3 in the presence of catalytic amount of H3PO4 produced intermediates 4, which were then transformed to isoindolines 5 with good 1,3-trans diastereoselectivity in the presence of K2CO3 by intramolecular aza-Michael addition. Sequential Ugi-azide and aza-Michael addition reaction of aldehydes 1, amines 2 and trimethylsilyl azide 6 also produced 4-tetrazolyl substituted isoindolines 8 with good 1,3-trans diastereoselectivity in the presence of potassium carbonate. |
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| Keywords: | Isoindoline Tetrazole Ugi reaction Aza-Michael addition Base catalyzed reaction CKOJJDMLOWVIBS-UHFFFAOYSA-N SKOGXMHVGTXGTH-UHFFFAOYSA-N SJWNECJPEMKKAT-UHFFFAOYSA-N KRXDOWCMQFKMOY-UHFFFAOYSA-N |
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