An intramolecular inverse electron demand Diels–Alder approach to annulated α-carbolines

Scholarly Works

• Gupta, A.; Khanal, P.; Laha, J. K. A Comprehensive Review on Construction of Biologically Active α‐Carbolines From Synthetic And Natural Origin. Asian Journal of Organic Chemistry 2024. doi:10.1002/ajoc.202400570
• Zaytsev, A. V.; Distler, P.; John, J.; Wilden, A.; Modolo, G.; Sims, M.; Lewis, F. W. Evaluation of Multidentate Ligands Derived from Ethyl 1,2,4-triazine-3-carboxylate Building Blocks as Potential An(III)-Selective Extractants for Nuclear Reprocessing. ChemistryOpen 2024, e202400306. doi:10.1002/open.202400306
• Banerjee, A.; Kundu, S.; Bhattacharyya, A.; Sahu, S.; Maji, M. S. Benzannulation strategies for the synthesis of carbazoles, indolocarbazoles, benzocarbazoles, and carbolines. Organic Chemistry Frontiers 2021, 8, 2710–2771. doi:10.1039/d1qo00092f
• Chen, X.; Li, L.; Wan, C.; Liu, J.-B. FeCl3-catalyzed sequential cyclization for the construction of 12-aryl 5,7-dihydropyrido[2,3-b:6,5-b']diindoles. Tetrahedron Letters 2020, 61, 152334. doi:10.1016/j.tetlet.2020.152334
• Xu, Y.; Chen, X.; Gao, Y.; Yan, Z.; Wan, C.; Liu, J.-B.; Wang, Z. Synthesis of Trifluoromethyl- and Ester Group-Substituted α-Carbolines via Iron-Catalyzed Tandem Cyclization Reaction. The Journal of organic chemistry 2020, 85, 4354–4364. doi:10.1021/acs.joc.0c00048
• Buttard, F.; Berthonneau, C.; Hiebel, M.-A.; Brière, J.-F.; Suzenet, F. Organocatalytic aza-Michael Reaction to 3-Vinyl-1,2,4-triazines as a Valuable Bifunctional Platform. The Journal of organic chemistry 2019, 84, 3702–3714. doi:10.1021/acs.joc.9b00141
• Sera, M.; Mizufune, H.; Ueda, T.; Mineno, M.; Zanka, A. Integrated Pd-catalyzed cross-coupling strategies for furnishing α-carbolines. Tetrahedron 2017, 73, 5946–5958. doi:10.1016/j.tet.2017.08.042
• Berthonneau, C.; Buttard, F.; Hiebel, M.-A.; Suzenet, F.; Brière, J.-F. Organocatalyzed Thia‐Michael Addition and Sequential Inverse Electron Demanding Diels‐Alder Reaction to 3‐Vinyl‐1,2,4‐ triazine Platforms. Advanced Synthesis & Catalysis 2017, 359, 4106–4110. doi:10.1002/adsc.201700831
• Yan, Q.; Gin, E.; Banwell, M. G.; Willis, A. C.; Carr, P. D. A Unified Approach to the Isomeric α-, β-, γ-, and δ-Carbolines via their 6,7,8,9-Tetrahydro Counterparts. The Journal of organic chemistry 2017, 82, 4328–4335. doi:10.1021/acs.joc.7b00323
• Wang, G.; You, X.; Gan, Y.; Liu, Y. Synthesis of δ- and α-Carbolines via Nickel-Catalyzed [2 + 2 + 2] Cycloaddition of Functionalized Alkyne-Nitriles with Alkynes. Organic letters 2016, 19, 110–113. doi:10.1021/acs.orglett.6b03385
• Ji, X.; Zhou, C.; Ji, K.; Aghoghovbia, R. E.; Pan, Z.; Chittavong, V.; Ke, B.; Wang, B. Click and Release: A Chemical Strategy toward Developing Gasotransmitter Prodrugs by Using an Intramolecular Diels–Alder Reaction. Angewandte Chemie 2016, 128, 16078–16083. doi:10.1002/ange.201608732
• Ji, X.; Zhou, C.; Ji, K.; Aghoghovbia, R. E.; Pan, Z.; Chittavong, V.; Ke, B.; Wang, B. Click and Release: A Chemical Strategy toward Developing Gasotransmitter Prodrugs by Using an Intramolecular Diels–Alder Reaction. Angewandte Chemie (International ed. in English) 2016, 55, 15846–15851. doi:10.1002/anie.201608732
• Tzvetkov, N. T.; Neumann, B.; Stammler, H.-G.; Antonov, L. A simple approach to multifunctionalized N1-alkylated 7-amino-6-azaoxindole derivatives using their in situ stabilized tautomer form. Tetrahedron 2016, 72, 6455–6466. doi:10.1016/j.tet.2016.08.055
• Laha, J. K.; Dayal, N. A Tandem Approach to Functionalized Carbazoles from Indoles via Two Successive Regioselective Oxidative Heck Reactions Followed by Thermal Electrocyclization. Organic letters 2015, 17, 4742–4745. doi:10.1021/acs.orglett.5b02265
• Khasanov, A. F.; Kopchuk, D. S.; Kovalev, I. S.; Taniya, O. S.; Zyryanov, G. V.; Rusinov, V. L.; Chupakhin, O. N. Reaction of lithium 2-arylethynides with 6-aryl-3-(2-pyridyl)-1,2,4-triazines as an access to 6-aryl-5-arylvinyl-3-(2-pyridyl)-1,2,4-triazines. Mendeleev Communications 2015, 25, 332–333. doi:10.1016/j.mencom.2015.09.003
• Wadsworth, A. D.; Naysmith, B. J.; Brimble, M. A. A review of the synthesis of α-carbolines. European journal of medicinal chemistry 2014, 97, 816–829. doi:10.1016/j.ejmech.2014.11.038
• Wiessler, M.; Waldeck, W.; Pipkorn, R.; Lorenz, P.; Debus, J.; Schrenk, H.-H.; Braun, K. The Diels—Alder‐Reaction with Inverse‐Electron‐Demand — A Review of an Efficient & Attractive Click‐Reaction Concept. ChemInform 2014, 45. doi:10.1002/chin.201441278
• Huntley, R.; Gurram, M.; Walker, J. R.; Jenkins, D. M.; Robé, E.; Ahmed, F. Synthesis of isoindolinones via inverse-electron demand Diels–Alder cycloadditions. Tetrahedron Letters 2014, 55, 2286–2289. doi:10.1016/j.tetlet.2014.02.093
• Alcaide, B.; Almendros, P.; Quirós, M. T. Gold/Acid‐Co‐catalyzed Direct Microwave‐Assisted Synthesis of Fused Azaheterocycles from Propargylic Hydroperoxides. Chemistry (Weinheim an der Bergstrasse, Germany) 2014, 20, 3384–3393. doi:10.1002/chem.201304509
• Zhang, X.; He, Q.; Xiang, H.-Y.; Shanshan, S.; Miao, Z.-H.; Yang, C. Rapid access to α-carbolines via a one-pot tandem reaction of α,β-unsaturated ketones with 2-nitrophenylacetonitrile and the anti-proliferative activities of the products. Organic & biomolecular chemistry 2014, 12, 355–361. doi:10.1039/c3ob41921e

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