Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

Scholarly Works

• Verochkina, E. A.; Fedoseeva, V. G.; Kondrashov, E. V.; Rozentsveig, I. B.; Larina, L. I.; Vashchenko, A. V.; Vchislo, N. V. Regioselectivity of conjugate addition of secondary amines and thiols to α-substituted enyne aldehydes. Tetrahedron 2025, 174, 134494. doi:10.1016/j.tet.2025.134494
• Sakla, A. P.; Aaghaz, S.; Ahmed, S.; Neshat, N.; Kamal, A. Recent Advancements in the Cyclization Strategies of 1,3-Enynes Towards the Synthesis of Heterocyclic/Carbocyclic Frameworks. Chemistry, an Asian journal 2025, e202401657. doi:10.1002/asia.202401657
• Dong, C.; Zhang, Y.; Hu, C.; Zhou, Y.; Li, J. Iodine‐Catalyzed Aerobic Oxidative Domino Cyclization of Methyl N‐Heteroarenes with 6‐Aminopyrimidine‐2,4‐Dione and Pyrazol‐5‐Amine. Asian Journal of Organic Chemistry 2025. doi:10.1002/ajoc.202400714
• Yan, F.; Zhang, X.; Li, D.; Zhu, N.; Bao, H. Recent Applications of the Sonogashira Reaction in the Synthesis of Drugs and Their Derivatives: A Review. Applied Organometallic Chemistry 2024, 39. doi:10.1002/aoc.7932
• Hsu, C.; Liu, Y.; Liu, S. Preparation of naphthalenes via Pd‐catalyzed annulation of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes under Suzuki‐Miyaura coupling conditions. Journal of the Chinese Chemical Society 2024, 71, 1300–1308. doi:10.1002/jccs.202400215
• Hsu, C.-K.; Liu, Y.-H.; Liu, S.-T. Preparation of Benzo[a]fluorenes via Pd-Catalyzed Annulation of 5-(2-Bromophenyl)pent-3-en-1-ynes. The Journal of organic chemistry 2024, 89, 12341–12348. doi:10.1021/acs.joc.4c01286
• Sharadha, N.; Haritha Kumari, A.; Jannapu Reddy, R. Transition‐Metal‐Free Annulation of Sulfonyl‐Derived 1,3‐Enynes: Simple and Efficient Construction of 2,4‐Disubstituted Thiophenes and Vinyl Sulfone‐Tethered 1,2,3‐NH‐Triazoles. Asian Journal of Organic Chemistry 2024, 13. doi:10.1002/ajoc.202400211
• de las Heras, L. A.; Esteruelas, M. A.; Oliván, M.; Oñate, E. Homo- and Cross-Coupling of Phenylacetylenes and α-Hydroxyacetylenes Catalyzed by a Square-Planar Rhodium Monohydride. ACS Catalysis 2024, 14, 8389–8404. doi:10.1021/acscatal.4c00264
• Zhang, Y.; Ning, L.; Zhu, T.; Xie, Z.; Dong, S.; Feng, X.; Liu, X. Chiral guanidine catalyzed cyclization reactions of 1,3-enynes for lactone synthesis: switchable H-bond catalysis. Organic Chemistry Frontiers 2024, 11, 2897–2904. doi:10.1039/d4qo00374h
• Jian, W.; Chiou, M.-F.; Li, Y.; Bao, H.; Yang, S. Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters 2024, 35, 108980. doi:10.1016/j.cclet.2023.108980
• Wang, K.; Gao, S.; Luo, Y.; Yao, Z. Synthesis and catalytic activity of half‐sandwich iridium complexes with acylhydrazone ligands for N‐alkylation of hydrazides under mild conditions. Applied Organometallic Chemistry 2024, 38. doi:10.1002/aoc.7473
• Medvedkov, I. A.; Nikolayev, A. A.; Yang, Z.; Goettl, S. J.; Mebel, A. M.; Kaiser, R. I. Elucidating the chemical dynamics of the elementary reactions of the 1-propynyl radical (CH3CC; X2A1) with 2-methylpropene ((CH3)2CCH2; X1A1). Physical chemistry chemical physics : PCCP 2024, 26, 6448–6457. doi:10.1039/d3cp05872g
• Luo, D.; Niu, S.; Gong, F.; Xu, C.; Lan, S.; Liu, J.; Yang, S.; Fang, X. Copper-Catalyzed Asymmetric Yne-Allylic Substitution Using Electron-Rich Arenes. ACS Catalysis 2024, 14, 2746–2757. doi:10.1021/acscatal.3c06146
• Yu, Z.; Li, J.; Cao, Y.; Dong, T.; Xiao, Y. 3-Trifluoromethyl Pyrrole Synthesis Based on β-CF3-1,3-Enynamides. The Journal of organic chemistry 2023, 88, 15501–15506. doi:10.1021/acs.joc.3c01790
• Reddy, C. R.; Ganesh, V.; Punna, N. Aminative annulation of cyano-enynyl esters leading to functionalized cyclopentenones. Chemical communications (Cambridge, England) 2023, 59, 8600–8603. doi:10.1039/d3cc02213g
• Rogalski, S.; Szymaszek, N.; Pietraszuk, C. The Regio- and Stereoselective Synthesis of 1,4-Diarylbut-1-en-3-ynes Having Aryl Groups at the Mutual Syn Positions. Organics 2023, 4, 206–218. doi:10.3390/org4020017
• Burgio, A. L.; Buchbinder, N. W.; Santos, W. L. Regio- and Stereoselective Copper-Catalyzed Borylation-Protodeboronation of 1,3-Diynes: Access to (Z)-1,3-Enynes. Organic letters 2023, 25, 2652–2656. doi:10.1021/acs.orglett.3c00711
• Soltani, F.; Bikas, R.; Heydari, N.; Kozakiewicz-Piekarz, A. Dinuclear oxidovanadium complexes with dihydrazone ligands derived from diethyl 2,6-dimethylpyridine-3,5-dicarboxylate obtained from Hantzsch reaction; crystal structure and catalytic activity. New Journal of Chemistry 2023, 47, 6102–6113. doi:10.1039/d2nj06279h
• Li, S.; Yang, W.; Shi, J.; Dan, T.; Han, Y.; Cao, Z.-C.; Yang, M. Synthesis of Trifluoromethyl-Substituted Allenols via Catalytic Trifluoromethylbenzoxylation of 1,3-Enynes. ACS Catalysis 2023, 13, 2142–2148. doi:10.1021/acscatal.2c04978
• Nan, N.; Wu, S.; Qin, J.; Li, J. State-of-Art Advances on Silylation-Initiated Annulation Reactions. Chinese Journal of Organic Chemistry 2023, 43, 3414. doi:10.6023/cjoc202307025

Explore citations to this article at