56857-96-6Relevant articles and documents
Substrate or Solvent-Controlled PdII-Catalyzed Regioselective Arylation of Quinolin-4(1H)-ones Using Diaryliodonium Salts: Facile Access to Benzoxocine and Aaptamine Analogues
Mehra, Manish K.,Sharma, Shivani,Rangan, Krishnan,Kumar, Dalip
supporting information, p. 2409 - 2413 (2020/03/16)
Regioselective C3, C5, and C8 arylation of quinolin-4(1H)-ones have been accomplished either by substrate-control or by tuning the reaction solvent. A variety of aryl(mesityl)iodonium triflates could smoothly deliver arylated products in good to excellent yields. Additionally, it offers great flexibility by arylating medicinally potent quinolone related heterocycles such as acridin-9(10H)-one, and phenanthridin-6(5H)-one under standard reaction conditions. This strategy was further extended with diphenyleneiodonium triflate to access oxacine fused quinolines. The post-modifications of synthesized products enhance the further utility of this protocol in organic synthesis. To the best of our knowledge, this is the first report on C5 arylation of quinolin-4(1H)-ones using iodine(III) reagents.
Efficient construction of 3-arylquinolin-4(1H)-ones via in situ Meinwald rearrangement/intramolecular reductive cyclization of 2′-nitrochalcone epoxides
Wang, Sheng,Zhao, Chao,Liu, Ting,Yu, Lifang,Yang, Fan,Tang, Jie
, p. 7025 - 7031 (2016/10/14)
An efficient method for construction of 3-arylquinolin-4(1H)-ones via in situ Meinwald rearrangement/intramolecular reductive cyclization of 2′-nitrochalcone epoxides has been developed. The practical approach is of excellent functional groups compatibili
Ohmic Heating-Assisted Synthesis of 3-Arylquinolin-4(1H)-ones by a Reusable and Ligand-Free Suzuki-Miyaura Reaction in Water
Pinto, Joana,Silva, Vera L. M.,Silva, Ana M. G.,Santos, Luís M. N. B. F.,Silva, Artur M. S.
, p. 6649 - 6659 (2015/10/06)
Potential bioactive 3-arylquinolin-4(1H)-ones were synthesized under ohmic heating using an efficient, reusable, and ligand-free protocol developed for the Suzuki-Miyaura coupling of 1-substituted-3-iodoquinolin-4(1H)-ones with several boronic acids in water using Pd(OAc)2 as a catalyst and tetrabutylammonium bromide (TBAB) as the phase transfer catalyst. Good substrate generality, ease of execution, short reaction time, and practicability make this method exploitable for the generation of libraries of B ring-substituted 3-arylquinolin-4(1H)-ones. After a simple workup, the Pd/catalyst-H2O-TBAB system could be reused for at least seven cycles without significant loss of activity.