The facile construction of the phthalazin-1(2H)-one scaffold via copper-mediated C–H(sp²)/C–H(sp) coupling under mild conditions

Scholarly Works

• Wen, F.; Zhang, Y.; Zhang, Z.; Mu, H.; Cheng, L.; Wang, J.; He, B.; Li, Z.; Fu, R. One‐Pot Three‐Component Construction of (Z)‐3‐Benzylidene‐2‐(quinolin‐8‐yl)isoindolin‐1‐ones Through C(sp2)−H Bond Activation Using Calcium Carbide as a Solid Alkyne Source. ChemistrySelect 2024, 9. doi:10.1002/slct.202402448
• Ganapathisivaraja, P.; Rao, G. V. N.; Ramarao, A.; Tej, M. B.; Praneeth, M. S.; Kapavarapu, R.; Rao, M. V. B.; Pal, M. Ultrasound assisted Cu-catalyzed decarbonylative Sonogashira coupling-cyclization strategy: Synthesis and evaluation of 3-heteroarylmethylene isoindolin-1-ones against SIRT1. Journal of Molecular Structure 2022, 1250, 131788. doi:10.1016/j.molstruc.2021.131788
• Chinigo, G.; Feng, Y.; Hoy, S.; Lira, R.; Perry, M. A. Comprehensive Heterocyclic Chemistry IV - Pyridazines and Their Benzo Derivatives. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 1–85. doi:10.1016/b978-0-12-818655-8.00082-2
• Topolovčan, N.; Duplić, F.; Gredičak, M. Influence of N-Substitution in 3-Alkyl-3-hydroxyisoindolin-1-ones on the Stereoselectivity of Brønsted Acid-Catalyzed Synthesis of 3-Methyleneisoindolin-1-ones. European Journal of Organic Chemistry 2021, 2021, 3920–3924. doi:10.1002/ejoc.202100400
• Xiong, F.; Li, B.; Yang, C.; Zou, L.; Ma, W.; Gu, L.; Mei, R.; Ackermann, L. Copper-mediated oxidative C-H/N-H activations with alkynes by removable hydrazides. Beilstein journal of organic chemistry 2021, 17, 1591–1599. doi:10.3762/bjoc.17.113
• Wootton, T. L.; Porter, J. A.; Grewal, K. S.; Chirila, P. G.; Forbes, S.; Coles, S. J.; Horton, P. N.; Hamilton, A. J.; Whiteoak, C. J. Merging Cu-catalysed C–H functionalisation and intramolecular annulations: computational and experimental studies on an expedient construction of complex fused heterocycles. Organic Chemistry Frontiers 2020, 7, 1235–1242. doi:10.1039/d0qo00283f
• Tian, C.; Dhawa, U.; Scheremetjew, A.; Ackermann, L. Cupraelectro-Catalyzed Alkyne Annulation: Evidence for Distinct C–H Alkynylation and Decarboxylative C–H/C–C Manifolds. ACS Catalysis 2019, 9, 7690–7696. doi:10.1021/acscatal.9b02348
• Chen, S.-Q.; Jiao, J.-Y.; Zhang, X.-G.; Zhang, X.-H. Ni(II)-catalyzed C(sp2) H alkynylation/annulation cascades: Regioselective access to 3-methyleneisoindoline-1-one using N,S-bidentate auxiliary. Tetrahedron 2019, 75, 246–252. doi:10.1016/j.tet.2018.11.051
• Youn, S. W.; Ko, T. Y.; Kim, Y. H.; Kim, Y. A. Pd(II)/Cu(II)-Catalyzed Regio- and Stereoselective Synthesis of (E)-3-Arylmethyleneisoindolin-1-ones Using Air as the Terminal Oxidant. Organic letters 2018, 20, 7869–7874. doi:10.1021/acs.orglett.8b03409
• Terán, C.; Besada, P.; Vila, N.; Costas-Lago, M. C. Recent advances in the synthesis of phthalazin-1(2H)-one core as a relevant pharmacophore in medicinal chemistry. European journal of medicinal chemistry 2018, 161, 468–478. doi:10.1016/j.ejmech.2018.10.047
• Hazarika, D.; Phukan, P. Copper‐Catalyzed Stereoselective Domino Synthesis of (Z)‐3‐Methyleneisoindolin‐1‐one. ChemistrySelect 2018, 3, 2474–2478. doi:10.1002/slct.201702875
• Lee, W.-C. C.; Wang, W.; Li, J. J. Copper(II)-Mediated ortho-Selective C(sp2)-H Tandem Alkynylation/Annulation and ortho-Hydroxylation of Anilides with 2-Aminophenyl-1H-pyrazole as a Directing Group. The Journal of organic chemistry 2018, 83, 2382–2388. doi:10.1021/acs.joc.7b02893
• Shibata, K.; Natsui, S.; Chatani, N. Rhodium-Catalyzed Alkenylation of C–H Bonds in Aromatic Amides with Alkynes. Organic letters 2017, 19, 2234–2237. doi:10.1021/acs.orglett.7b00709
• Zhu, W.; Wang, B.; Zhou, S.; Liu, H. The Facile Construction of the Phthalazin‐1(2H)‐one Scaffold via Copper‐Mediated C—H(sp2)/C—H(sp) Coupling under Mild Conditions. ChemInform 2015, 46. doi:10.1002/chin.201549106

Explore citations to this article at