103724-32-9Relevant articles and documents
Ru(II)-Catalyzed C-H Hydroxyalkylation and Mitsunobu Cyclization of N-Aryl Phthalazinones
Ghosh, Prithwish,Han, Sang Hoon,Jeoung, Daeun,Kim, In Su,Kim, Kunyoung,Kim, Saegun,Kim, Seung Jun,Ku, Jin-Mo,Mishra, Neeraj Kumar
, p. 2520 - 2531 (2020/03/13)
Ruthenium(II)-catalyzed C(sp2)-H functionalization of N-Aryl phthalazinones with a range of aldehydes and activated ketone is described. Initial formation of hydroxyalkylated phthalazinones and subsequent Mitsunobu cyclization provided facile access to biologically relevant indazolophthalazinones. The utility of this method is highlighted by synthetic transformations into a series of potentially bioactive scaffolds.
Phthalazinone-Assisted C-H Amidation Using Dioxazolones under Rh(III) Catalysis
Jeoung, Daeun,Kim, Kunyoung,Han, Sang Hoon,Ghosh, Prithwish,Lee, Suk Hun,Kim, Saegun,An, Won,Kim, Hyung Sik,Mishra, Neeraj Kumar,Kim, In Su
, p. 7014 - 7023 (2020/07/07)
The preparation of phthalazinone derivatives is pivotal for their utilization as pharmaceutical agents and other entities. Herein, we report the phthalazinone-assisted carbon-nitrogen bond forming reaction using dioxazolones as robust amidation sources under Rh(III) catalysis. The broad functional group tolerance and complete site-selectivity are observed. Notably, a series of transformations of synthesized compounds into biologically relevant N-heterocycles demonstrates the applicability of the developed methodology.
Palladium-Catalyzed Direct ortho-C–H Bond Sulfonylation and Halogenation of Phthalazine-1,4-diones
Dabiri, Minoo,Lehi, Noushin Farajinia,Osmani, Chiman,Movahed, Siyavash Kazemi
, p. 7247 - 7254 (2019/12/03)
The regio- and chemo-selective Pd-catalyzed C–H activation methods have been successfully reported for directed C–H sulfonation and halogenation of pyridazinedione with arylsulfonyl chlorides and N-halosuccinimide, respectively. These protocols are compatible with a range of various functional groups and exhibit excellent regio-selectivity under mild reaction conditions by use of inexpensive and readily accessible reagents.
Ru(II)-Catalyzed C-H Activation and Annulation Reaction via Carbon-Carbon Triple Bond Cleavage
Prakash, Rashmi,Bora, Bidisha R.,Boruah, Romesh C.,Gogoi, Sanjib
supporting information, p. 2297 - 2300 (2018/04/30)
An unprecedented Ru(II)-catalyzed C-H activation and annulation reaction, which proceeds via C-C triple bond cleavage, is reported. This reaction of 2-phenyldihydrophthalazinediones with alkynes, which works most efficiently in the presence of bidented ligand 1,3-bis(diphenylphosphino)propane, affords good yields of substituted quinazolines.
Expedient synthesis of new cinnoline diones by Ru-catalyzed regioselective unexpected deoxygenation-oxidative annulation of propargyl alcohols with phthalazinones and pyridazinones
Rajkumar, Subramani,Antony Savarimuthu,Senthil Kumaran, Rajendran,Nagaraja,Gandhi, Thirumanavelan
supporting information, p. 2509 - 2512 (2016/02/12)
Ruthenium-catalyzed simple, cascade and one-pot synthesis of cinnoline-fused diones has been carried out by the C-H activation of phthalazinones/pyridazinones accomplished by the unusual deoxygenation of propargyl alcohols. The bond selectivity is accredited to the traceless directing nature of the hydroxyl group of propargyl alcohol. A sequential C-H activation, insertion and deoxy-oxidative annulation has been proposed based on the preliminary mechanistic study.
Synthesis of cinnolines via Rh(III)-catalysed dehydrogenative C-H/N-H functionalization: Aggregation induced emission and cell imaging
Mayakrishnan, Sivakalai,Arun, Yuvaraj,Balachandran, Chandrasekar,Emi, Nobuhiko,Muralidharan, Doraiswamy,Perumal, Paramasivan Thirumalai
supporting information, p. 1958 - 1968 (2016/02/18)
Rhodium catalysed dehydrogenative C-H/N-H functionalization was developed to construct phthalazino[2,3-a]-/indazolo[1,2-a]cinnolines by reacting N-phenyl phthalazine/indazole with alkynes. The synthesized compounds exhibit prominent fluorescence properties in solid and aggregation states. Their application in cell imaging was investigated using various cancer cell lines.
Phthalazinone pyrazoles as potent, selective, and orally bioavailable inhibitors of Aurora-A kinase
Prime, Michael E.,Courtney, Stephen M.,Brookfield, Frederick A.,Marston, Richard W.,Walker, Victoria,Warne, Justin,Boyd, Andrew E.,Kairies, Norman A.,Von Der Saal, Wolfgang,Limberg, Anja,Georges, Guy,Engh, Richard A.,Goller, Bernhard,Rueger, Petra,Rueth, Matthias
experimental part, p. 312 - 319 (2011/03/20)
The inhibition of Aurora kinases in order to arrest mitosis and subsequently inhibit tumor growth via apoptosis of proliferating cells has generated significant discussion within the literature. We report a novel class of Aurora kinase inhibitors based upon a phthalazinone pyrazole scaffold. The development of the phthalazinone template resulted in a potent Aurora-A selective series of compounds (typically >1000-fold selectivity over Aurora-B) that display good pharmacological profiles with significantly improved oral bioavailability compared to the well studied Aurora inhibitor VX-680.
