Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones

Scholarly Works

• Lee, H.; Nam, H.; Lee, S. Y. Enantio- and Diastereoselective Variations on α-Iminonitriles: Harnessing Chiral Cyclopropenimine-Thiourea Organocatalysts. Journal of the American Chemical Society 2024, 146, 3065–3074. doi:10.1021/jacs.3c09911
• Kamboj, M.; Bajpai, S.; Banik, B. K. Microwave-induced Reactions for Pyrrole Synthesis. Current Organic Chemistry 2023, 27, 559–567. doi:10.2174/1385272827666230508124450
• Zhao, L.; Yan, Y.; Wei, Z.-L.; Liao, W.-W. Organocatalytic Allylic Alkylation of α-(Alkylideneamino)nitriles and Its Application in the Preparation of Multisubstituted 1-Pyrrolines. The Journal of organic chemistry 2022, 87, 10090–10104. doi:10.1021/acs.joc.2c01072
• Filippov, I. P.; Novikov, M. S.; Khlebnikov, A. F.; Rostovskii, N. V. One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2H-azirines and Diazocarbonyl Compounds. The Journal of organic chemistry 2022, 87, 8835–8840. doi:10.1021/acs.joc.2c00977
• Tarasova, O. A.; Trofimov, B. A.; Maximova, M. A.; Albanov, A. I.; Nedolya, N. A. Towards Rare-Functionalized N-Alkenyl-1H-pyrroles via Regioselectively Metalated N-Isopropenyl-1H-pyrroles. Synthesis 2022, 54, 2516–2526. doi:10.1055/a-1736-4200
• Philkhana, S. C.; Badmus, F. O.; Dos Reis, I. C.; Kartika, R. Recent Advancements in Pyrrole Synthesis. Synthesis 2021, 53, 1531–1555. doi:10.1055/s-0040-1706713
• Annor-Gyamfi, J. K.; Ametsetor, E.; Meraz, K.; Bunce, R. A. Naphthalenes and Quinolines by Domino Reactions of Morita-Baylis-Hillman Acetates. Molecules (Basel, Switzerland) 2020, 25, 5168. doi:10.3390/molecules25215168
• Duc, D. X. Recent Progress in the Synthesis of Pyrroles. Current Organic Chemistry 2020, 24, 622–657. doi:10.2174/1385272824666200228121627
• Tarasova, O. A.; Nedolya, N. A.; Albanov, A. I.; Trofimov, B. A. 2-Amino-5-(cyanomethylsulfanyl)-1H-pyrroles from Propargylamines, Isothiocyanates, and Bromoacetonitrile by One-Pot Synthetic Protocol. ChemistrySelect 2020, 5, 5726–5731. doi:10.1002/slct.202000577
• Tarasova, O. A.; Nedolya, N. A.; Albanov, A. I.; Trofimov, B. A. Cyclizations of The Isothiocyanates-Derived Azatrienes: The CuBr–Catalyzed Switching from Thiophenes to Pyrroles. European Journal of Organic Chemistry 2018, 2018, 5961–5971. doi:10.1002/ejoc.201800987
• Netz, N.; Díez-Poza, C.; Barbero, A.; Opatz, T. Modular De Novo Synthesis of Unsymmetrical BODIPY Dyes possessing four different Aryl Substituents. European Journal of Organic Chemistry 2017, 2017, 4580–4599. doi:10.1002/ejoc.201700773
• Nebe, M. M.; Kucukdisli, M.; Opatz, T. 3,4-Dihydro-2H-pyrrole-2-carbonitriles: Useful Intermediates in the Synthesis of Fused Pyrroles and 2,2'-Bipyrroles. The Journal of organic chemistry 2016, 81, 4112–4121. doi:10.1021/acs.joc.6b00393
• Mir, N. A.; Choudhary, S.; Ramaraju, P.; Singh, D.; Kumar, I. Microwave assisted aminocatalyzed [3 + 2] annulation between α-iminonitriles and succinaldehyde: synthesis of pyrrole-3-methanols and related polycyclic ring systems. RSC Advances 2016, 6, 39741–39749. doi:10.1039/c6ra06831f
• Opatz, T.; Kucukdisli, M.; Nebe, M. M.; Bartelt, S. M. A Short Synthesis of 2,3,5-Trisubstituted Pyrroles by an Alkylation/Dehydrocyanation Sequence. HETEROCYCLES 2016, 93, 378. doi:10.3987/com-15-s(t)15
• Tsutomu, F.; Mizuho, A.; Masatomo, I. Regioselective Synthesis of 2,4-Differentially Arylated Pyrroles and Its Application to The Synthesis of Lamellarins. HETEROCYCLES 2016, 93, 593–612. doi:10.3987/com-15-s(t)49
• Sharma, A.; Piplani, P. Microwave‐activated Synthesis of Pyrroles: A Short Review. Journal of Heterocyclic Chemistry 2015, 54, 27–34. doi:10.1002/jhet.2550
• Tauber, J.; Opatz, T. 2-Aminoacetonitrile. Encyclopedia of Reagents for Organic Synthesis 2015, 1–4. doi:10.1002/047084289x.rn01752
• Narule, M. N.; Gaidhane, M. K.; Gaidhane, P. K.
• Imbri, D.; Netz, N.; Kucukdisli, M.; Kammer, L. M.; Jung, P.; Kretzschmann, A.; Opatz, T. One-Pot Synthesis of Pyrrole-2-carboxylates and -carboxamides via an Electrocyclization/Oxidation Sequence. The Journal of organic chemistry 2014, 79, 11750–11758. doi:10.1021/jo5021823
• Otto, N.; Opatz, T. Heterocycles from α-aminonitriles. Chemistry (Weinheim an der Bergstrasse, Germany) 2014, 20, 13064–13077. doi:10.1002/chem.201403956

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