Abstract:
A practically convenient synthesis of (E)-3-arylidene-4-diazopyrrolidine-2,5-diones from N-substituted maleimides via the Wittig reaction and the Regitz diazo transfer has been developed. In all 26 cases studied, only one chromatographic purification was required with no need for aqueous workup, which makes this protocol amenable to producing the emerging class of diazo compounds in parallel format.
Citation:
E. G. Chupakhin, G. P. Kantin, D. V. Dar'in, M. Yu. Krasavin, “Convenient preparation of (E)-3-arylidene-4-diazopyrrolidine-2,5-diones in array format”, Mendeleev Commun., 31:1 (2021), 36–38
Linking options:
https://www.mathnet.ru/eng/mendc826
https://www.mathnet.ru/eng/mendc/v31/i1/p36
This publication is cited in the following 13 articles:
Alexander Kazantsev, Ivan A. Rodionov, Olga Bakulina, Grigory Kantin, Dmitry Dar'in, Mikhail Krasavin, “Catalyst Loading Controls Chemoselectivity: Unusual Effect in Rhodium(II) Carbene Insertion Reactions with Tetrahydrofuran”, Catalysts, 13:2 (2023), 428
Hong‐Li Ruan, Wen Zhang, Xiao‐Han Rao, Zhi‐Jia Zhu, Sheng‐Yin Zhao, “KI‐Facilitated Trifunctionalization of Maleimides in Water: Access to Disulfonylated Diazosuccinimide Derivatives and their Synthetic Applications”, Adv Synth Catal, 365:22 (2023), 4008
Wen-Sheng Li, Jian Zhang, Sen Lu, Guo Cheng, Wen-Juan Wan, Li-Xin Wang, “A copper catalyzed Doyle–Kirmse reaction for the concise and effective preparation of multifunctional 3-allyl-3-(thio) succinimides”, Tetrahedron Letters, 122 (2023), 154506
Debasish Laha, Kajal B. Meher, Onkar S. Bankar, Ramakrishna G. Bhat, “Silver‐Catalyzed One‐Pot Access to Diastereoselective Benzo[5,6]oxepino[2,3‐c]pyrroles via Formal (5+2)‐Annulation of Donor‐/Acceptor‐Type Aryl Vinyl Diazosuccinimide with Ketones”, Asian J Org Chem, 11:4 (2022)
Anastasia Vepreva, Alexander S Bunev, Andrey Yu Kudinov, Grigory Kantin, Mikhail Krasavin, Dmitry Dar'in, “Unusual highly diastereoselective Rh(II)-catalyzed dimerization of 3-diazo-2-arylidenesuccinimides provides access to a new dibenzazulene scaffold”, Beilstein J. Org. Chem., 18 (2022), 533
Anastasia Vepreva, Grigory Kantin, Mikhail Krasavin, Dmitry Dar'in, “A General Way to Spiro-Annulated 2-Benzoxepines via Rh2(esp)2-Catalyzed [5+2] Cycloaddition of Diazo Arylidene Succinimides to Ketones”, Synthesis, 54:22 (2022), 5128
E. G. Chupakhin, G. P. Kantin, D. V. Dar'in, M. Yu. Krasavin, “Novel chromeno[2,3-c]pyrroles synthesized via intramolecular rhodium(ii) carbene trapping”, Mendeleev Commun., 32:3 (2022), 382–383
P. Paramonova, T. Sharonova, S. A. Kalinin, E. G. Chupakhin, A. S. Bunev, M. Yu. Krasavin, “(E)-3-Arylidene-4-diazopyrrolidine-2,5-diones conveniently elaborated into cytotoxic compounds bearing primary sulfonamide and Michael acceptor moieties”, Mendeleev Commun., 32:2 (2022), 176–177
Evgeny Chupakhin, Olga Bakulina, Dmitry Dar'in, Mikhail Krasavin, “Facile entry into the 1H-pyrrolo[3,4-b]indolizine-1,3(2H)-dione scaffold via intramolecular Rh(II) carbene trapping”, Tetrahedron Letters, 85 (2021), 153467
Anna Inyutina, Grigory Kantin, Dmitry Dar′in, Mikhail Krasavin, “Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes: A Route to 2-Benzoxepines”, J. Org. Chem., 86:19 (2021), 13673
Anna Inyutina, Dmitry Dar'in, Grigory Kantin, Mikhail Krasavin, “Tricyclic 2-benzazepines obtained via an unexpected cyclization involving nitrilium ylides”, Org. Biomol. Chem., 19:23 (2021), 5068
Haoxuan Yuan, Kemiao Hong, Xiangrong Liu, Yu Qian, Xinfang Xu, Wenhao Hu, “Enantioselective assembly of 3,3-disubstituted succinimides via three-component reaction of vinyl diazosuccinimides with alcohols and imines”, Chem. Commun., 57:65 (2021), 8043
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