199168-51-9Relevant articles and documents
Visible-light-induced photoxidation-Povarov cascade reaction: synthesis of 2-arylquinoline through alcohol andN-benzylanilines under mild conditionsviaAg/g-C3N4nanometric semiconductor catalyst
Wang, Peng,Wang, Xiaowen,Niu, Xiyu,Zhu, Li,Yao, Xiaoquan
, p. 4840 - 4843 (2020)
With a Ag/g-C3N4nanometric semiconductor as the photocatalyst, 2-arylquinolines were synthesized through a photoxidation-Povarov cascade reaction ofN-benzylanilines and alcohols under visible light irradiation. Under the blue light of a 3 W LED, good yields were achieved for various substrates in oxygen at room temperature. This methodology provides a green and mild alternative for the formation of 2-arylquinoline derivatives. Remarkably, the Ag/g-C3N4nanocomposite can be conveniently recovered and reused several times with satisfying yields.
A Domino Heck Coupling-Cyclization-Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines
Ghora, Santanu,Sreenivasulu, Chinnabattigalla,Satyanarayana, Gedu
, p. 393 - 402 (2021/10/21)
An efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence. Notably, this protocol occurs in water as a green solvent. Significantly, the method exhibits broad substrate scope and is applied for the synthesis of deuterated quinolines through a deuterium-exchange process.
Direct C-H Arylation and Alkylation of Electron-Deficient Heteroaromatic Compounds with Organozinc Reagents
Peng, Zhihua,Yu, Chuanman,Wang, Yilei,Wei, Dongyue,Jiang, Cuiyu
, p. 3678 - 3688 (2021/11/16)
A direct and convenient method for the C-H arylation and alkylation of electron-deficient N-heteroarenes with readily available organozinc reagents has been developed. This transformation could be readily performed in the absence of a transition-metal catalyst and external oxidants, affording a wide range of substituted heteroarenes with good functional group tolerance in good to excellent yields. The developed simple protocol is scalable to the gram level and suitable for late-stage modification of bioactive molecules and drugs.
Facile synthesis of substituted quinolines by iron(iii)-catalyzed cascade reaction between anilines, aldehydes and nitroalkanes
Mahato, Sachinta,Mukherjee, Anindita,Santra, Sougata,Zyryanov, Grigory V.,Majee, Adinath
, p. 7907 - 7917 (2019/09/06)
A library of substituted quinolines has been synthesized by the reaction of aldehydes, anilines and nitroalkanes using a catalytic amount of Fe(iii) chloride. The reaction is a simple, efficient, one-pot, three-component domino strategy in ambient air which afforded the products in high yields. A probable pathway of the reaction is a sequential aza-Henry reaction/cyclization/denitration. The use of commercially available chemicals as starting materials, an inexpensive metal catalyst, aerobic reaction conditions, tolerance of a wide range of functional groups, and operational simplicity are the notable advantages of this present protocol.
Iron-Catalyzed Aerobic Dehydrogenative Kinetic Resolution of Cyclic Secondary Amines
Lu, Ran,Cao, Liya,Guan, Honghao,Liu, Lei
, p. 6318 - 6324 (2019/05/09)
A nonenzymatic iron-catalyzed dehydrogenative kinetic resolution of cyclic secondary amines using air as an oxidant has been reported. The economical and practical method is applicable to a series of cyclic benzylic amines, including 5,6-dihydrophenanthridines and 1,2-dihydroquinolines, with diverse functional groups at the α position in high yields with excellent enantioselectivities. The direct dehydrogenative kinetic resolution of advanced intermediates of bioactive molecules that are difficult to access using existing catalytic asymmetric synthetic strategy was also demonstrated.
Three-Component Povarov Reaction with Alcohols as Alkene Precursors: Efficient Access to 2-Arylquinolines
Li, Xinjian,Xing, Qi,Li, Pan,Zhao, Jingjing,Li, Fuwei
supporting information, p. 618 - 625 (2017/02/05)
An atom-economic and efficient approach to the synthesis of 2-arylquinolines has been developed. The protocol involves an iron-catalysed cascade N-alkylation/aerobic oxidation/Povarov reaction, and the desired quinolines were prepared in moderate to excellent yields from readily accessible anilines, aldehydes, and EtOH/nPrOH, with water as the only side-product. The aniline substrates also act as a recyclable transfer medium for EtOH/nPrOH through an in-situ N-alkylation/oxidation process. This makes EtOH/nPrOH an economical and environmentally friendly precursor of alkenes as well as the solvent.
Synthesis of quinolines by a solid acid-catalyzed microwave-assisted domino cyclization-aromatization approach
De Paolis, Omar,Teixeira, Liliana,T?r?k, Béla
experimental part, p. 2939 - 2942 (2009/07/26)
A microwave-assisted solid acid-catalyzed synthesis of quinolines from anilines and cinnamaldehydes is described. Use of montmorillonite K-10 results in a one-pot process; the cyclization and oxidation steps readily take place in a domino approach. Reactions were completed in a matter of minutes and provided excellent yields. The efficient and ecofriendly catalyst and the convenience of the product isolation make this process an attractive alternative for the synthesis of these important heterocycles.
