38035-81-3Relevant articles and documents
Palladium-catalyzed carbonylative synthesis of 3-arylquinolin-2(1H)-ones from benzyl chlorides and o-nitrobenzaldehydes
Hou, Chen-Yang,Liu, Jian-Li,Qi, Xinxin,Wu, Xiao-Feng
, (2021/09/02)
A palladium-catalyzed carbonylative cyclization of benzyl chlorides with o-nitrobenzaldehydes has been developed for the synthesis of 3-arylquinolin-2(1H)-ones. Mo(CO)6 played a dual role as both a CO surrogate and a reductant in this carbonylative transformation.
Palladium-catalyzed carbonylative cyclization of benzyl chlorides with anthranils for the synthesis of 3-arylquinolin-2(1: H)-ones
Liu, Jian-Li,Xu, Ren-Rui,Wang, Wei,Qi, Xinxin,Wu, Xiao-Feng
, p. 3584 - 3588 (2021/05/04)
An efficient carbonylative procedure for the synthesis of 3-arylquinoin-2(1H)-ones has been established. Through a palladium-catalyzed aminocarbonylation of benzyl chlorides with anthranils, a variety of 3-arylquinoin-2(1H)-one products were obtained in moderate to excellent yields with good functional group tolerance. This journal is
Palladium-Catalyzed Reductive Aminocarbonylation of Benzylammonium Triflates with o-Nitrobenzaldehydes for the Synthesis of 3-Arylquinolin-2(1 H)-ones
Liu, Yongzhu,Qi, Xinxin,Wu, Xiao-Feng
, p. 13824 - 13832 (2021/10/12)
A palladium-catalyzed straightforward procedure for the synthesis of 3-arylquinolin-2(1H)-ones has been developed. The synthesis proceeds through a palladium-catalyzed reductive aminocarbonylation reaction of benzylic ammonium triflates with o-nitrobenzaldehydes, and a wide range of 3-arylquinolin-2(1H)-ones was obtained in moderate to good yields with very good functional group compatibility.
Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones
Wang, Ya,Zhou, Yao,Ma, Xingxing,Song, Qiuling
, p. 5599 - 5604 (2021/08/01)
Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.
Preparation method of 3-aryl quinoline-2 (1H) ketone derivative
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Paragraph 0032-0040, (2021/07/01)
The invention discloses a preparation method of a 3-aryl quinoline-2 (1H) ketone derivative. The method comprises the following steps: carrying out a reaction on palladium acetate, S)-1, 1'-binaphthyl-2, 2'-diphenylphosphine, carbonyl molybdenum, triethylamine, water, benzisoxazole and a benzyl chloride compound at 100 DEG C for 26 hours, and after the reaction is completed, carrying out post-treatment to obtain the 3-aryl quinoline-2 (1H) ketone derivative. According to the preparation method, benzisoxazole is used as a nitrogen source and a formyl source, the operation is simple, the reaction initial raw materials are cheap and easy to obtain, the tolerance range of substrate functional groups is wide, and the reaction efficiency is high; and various 3-aryl quinoline-2 (1H) ketone derivatives can be synthesized according to actual needs, and the practicability of the method is widened while the operation is convenient.
Regio- And Stereoselective Synthesis of Diverse 3,4-Dihydro-2-quinolones through Catalytic Hydrative Cyclization of Imine- And Carbonyl-Ynamides with Water
Zhu, Bo-Han,Zhang, Ying-Qi,Xu, Hao-Jin,Li, Long,Deng, Guo-Cheng,Qian, Peng-Cheng,Deng, Chao,Ye, Long-Wu
, p. 1706 - 1713 (2021/02/09)
Transition-metal-catalyzed alkyne hydration reaction has attracted considerable interest in the past decades because this approach would lead to the facile and efficient formation of synthetically useful carbonyls. However, transition-metal-catalyzed alky
Palladium-Catalyzed C-C Bond Activation of Cyclopropenone: Modular Access to Trisubstituted α,β-Unsaturated Esters and Amides
Nanda, Tanmayee,Biswal, Pragati,Pati, Bedadyuti Vedvyas,Banjare, Shyam Kumar,Ravikumar, Ponneri Chandrababu
, p. 2682 - 2695 (2021/02/01)
Strain-driven palladium/N-heterocyclic carbene-catalyzed C-C bond activation of diphenylcyclopropenone (DPC) has been explored for one-step access to trisubstituted α,β-unsaturated esters and amides. The designed transformation works under mild conditions providing exclusively a single stereoisomer. Mechanistic studies support the oxidative addition of the C-C bond of cyclopropenone to in-situ-generated Pd(0) intermediate. We have proved that vinylic hydrogen in the product is coming from phenol/aniline through deuterium-labeling studies. Late-stage functionalization of bioactive molecules such as procaine, estrone, and hymecromone demonstrates the robustness of this protocol.
Supported Palladium Nanoparticles-Catalyzed Synthesis of 3-Substituted 2-Quinolones from 2-Iodoanilines and Alkynes Using Oxalic Acid as C1 Source
Thakur, Vandna,Sharma, Ajay,Yamini,Sharma, Nishtha,Das, Pralay
, p. 426 - 431 (2018/12/13)
3-Aryl/alkyl-2-quinolones were synthesized employing microwave assisted multicomponent reaction of 2-iodoanilines, terminal alkynes and oxalic acid dihydrate ((CO2H)2 ? 2H2O) under polystyrene supported palladium (Pd@PS) nanoparticles-catalyzed conditions. The use of a heterogeneous palladium catalyst was explored first time for 2-quinolone synthesis involving carbonylation reaction employing (CO2H)2 ? 2H2O as a solid and bench stable carbon monoxide (CO) source. The reaction exhibited good substrate generality for 2-iodoanilines and alkynes with wide functional group tolerance and good regio-selectivity. The ligand free operation, recyclability of heterogeneous Pd@PS catalyst and use of bench stable C1 source are the invaluable merits of the protocol. (Figure presented.).
Sulfinates and thiocyanates triggered 6-endo cyclization of o-alkynylisocyanobenzenes
Khaikate, Onnicha,Meesin, Jatuporn,Pohmakotr, Manat,Reutrakul, Vichai,Leowanawat, Pawaret,Soorukram, Darunee,Kuhakarn, Chutima
supporting information, p. 8553 - 8558 (2018/12/01)
Diverse 2-sulfonyl- and 2-thiocyanato-3-substituted quinolines were synthesized from o-alkynylisocyanobenzenes by nucleophilic addition of the respective sulfinate sodium salts and ammonium thiocyanate to the isocyanide moiety followed by cyclization. The salient features of the methodology include metal-free, ambient temperature and mild reaction conditions, ease of reagent handling, and broad functional group tolerance.
Synthesis of 3-substituted quinolin-2(1H)-ones via the cyclization of o-alkynylisocyanobenzenes
Charoenpol, Ailada,Meesin, Jatuporn,Khaikate, Onnicha,Reutrakul, Vichai,Pohmakotr, Manat,Leowanawat, Pawaret,Soorukram, Darunee,Kuhakarn, Chutima
, p. 7050 - 7054 (2018/10/17)
A facile synthesis of various functionalized 3-substituted quinolin-2(1H)-ones through Ag(i) nitrate-catalyzed cyclization of o-alkynylisocyanobenzenes is described. The reaction allows rapid and convenient access to 3-substituted quinolin-2(1H)-one scaffolds in moderate to good yields.
