Synthesis of pyrrolo[1,2-a]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts

Scholarly Works

• Molchanova, M. V.; Ikonnikova, V. A.; Smirnov, A. Y.; Solyev, P. N.; Baranov, M. S.; Mikhaylov, A. A. Synthesis of Spiro[imidazole‐4,3′‐pyrrolo[1,2‐a]quinolin]‐ 5‐ones via 1,3‐Dipolar Cycloaddition of Quinolinium Ylides with Arylydeneimidazol‐4‐ones. ChemistrySelect 2024, 9. doi:10.1002/slct.202305123
• Escolano, M.; Gaviña, D.; Alzuet-Piña, G.; Díaz-Oltra, S.; Sánchez-Roselló, M.; Pozo, C. D. Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines. Chemical reviews 2024, 124, 1122–1246. doi:10.1021/acs.chemrev.3c00625
• Mohammad-Salim, H.; Mondal, A.; de Julián-Ortiz, J. V.; Acharjee, N. Diastereoselective green synthesis of pyrrolo[1,2-a]quinolines via [3+2] cycloaddition reaction: insights from molecular electron density theory. Theoretical Chemistry Accounts 2023, 142. doi:10.1007/s00214-023-03068-8
• Alnamer, Y. A.; Ibrahim, M. A.; Ahmed, A.; Ali, N. M.; Badran, A.-S. Synthetic Approaches for Annulated Quinolines at Face a. Polycyclic Aromatic Compounds 2023, 1–24. doi:10.1080/10406638.2023.2225674
• Wang, Z.-H.; Zhang, T.; Shen, L.-W.; Yang, X.; Zhang, Y.-P.; You, Y.; Zhao, J.-Q.; Yuan, W.-C. Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N-Ylides and Electron-Deficient Olefins. Molecules (Basel, Switzerland) 2023, 28, 4410. doi:10.3390/molecules28114410
• Xiong, H.; Wu, J.; Qin, H.-L. [3 + 2] cycloaddition for the assembly of indolizine-based heterocyclic sulfonyl fluorides. Organic Chemistry Frontiers 2023, 10, 342–347. doi:10.1039/d2qo01466a
• Das, S. Recent Applications of Quinolinium Salts in the Synthesis of Annulated Heterocycles. SynOpen 2022, 6, 86–109. doi:10.1055/a-1834-2189
• Altowyan, M.; Soliman, S.; Haukka, M.; Al-Shaalan, N.; Alkharboush, A.; Barakat, A. Synthesis of Unexpected Dimethyl 2-(4-Chlorophenyl)-2,3-dihydropyrrolo[2,1-a]isoquinoline-1,3-dicarboxylate via Hydrolysis/Cycloaddition/Elimination Cascades: Single Crystal X-ray and Chemical Structure Insights. Crystals 2021, 12, 6. doi:10.3390/cryst12010006
• Badenock, J. C. Six-membered ring systems: pyridines and benzo derivatives. Progress in Heterocyclic Chemistry; Elsevier, 2021; Vol. 32, pp 397–430. doi:10.1016/b978-0-323-89812-6.00012-2
• Dong, S.; Fu, X.; Xu, X. [3+2]‐Cycloaddition of Catalytically Generated Pyridinium Ylide: A General Access to Indolizine Derivatives. Asian Journal of Organic Chemistry 2020, 9, 1133–1143. doi:10.1002/ajoc.202000276
• Cheng, L. C.; Chen, W. C.; Santhoshkumar, R.; Chao, T. H.; Cheng, M. J.; Cheng, C.-H. Synthesis of Quinolinium Salts from N‐Substituted Anilines, Aldehydes, Alkynes, and Acids: Theoretical Understanding of the Mechanism and Regioselectivity. European Journal of Organic Chemistry 2020, 2020, 2116–2129. doi:10.1002/ejoc.202000178
• Dada, R.; Sulthan, M.; Yaragorla, S. Calcium-Catalyzed Stereoselective Tandem [4+2] and [3+2] Annulation Reaction for the Synthesis of Dihydropyrrolo[1,2-a]quinolines. Organic letters 2019, 22, 279–283. doi:10.1021/acs.orglett.9b04293
• Choi, A.; Coldham, I. Three-component couplings for the synthesis of pyrroloquinoxalinones by azomethine ylide 1,3-dipolar cycloaddition chemistry. Tetrahedron Letters 2019, 60, 151023. doi:10.1016/j.tetlet.2019.151023

Explore citations to this article at