72002-24-5Relevant articles and documents
Organocatalyzed regioselective and enantioselective synthesis of 1,4- and 1,2-dihydropyridines
Le, Truong-Giang,Pham, Hoai-Thu,Martin, James P.,Chataigner, Isabelle,Renaud, Jean-Luc
supporting information, p. 2673 - 2684 (2020/08/07)
Herein, we introduce one of the first examples of asymmetric organocatalyzed synthesis of 1,2-dihydropyridines, affording enantioselective access to and partially solving regioselectivity challenges in the synthesis of dihydropyridines. We demonstrate that through modification of organocatalysts both 1,2- and 1,4-dihydropyridines (1,2- and 1,4-DHPs) can be obtained with high regioselectivity (ratio of 1,2-DHP/1,4-DHP from 95/5 to 0/100) and enantioselectivity (33% ee for 1,2-DHPs and up to 98% ee for 1,4-DHPs) in good yields (up to 87%).
Highly efficient and facile synthesis of β-enaminones catalyzed by diphenylammonium triflate
Zhao, Ting-Ting,Song, Jiang-Long,Hong, Feng-Qing,Xia, Jian-Sheng,Li, Jian-Jun
, p. 2857 - 2868 (2019/08/21)
Abstract: The catalytic performance of diphenylammonium triflates as an organocatalyst in the synthesis of β-enaminones from various substituted β-diketones and amides (or amines) were evaluated. A wide range of β-enaminones were efficiently synthesized in good to excellent yields under mild reaction conditions. Applying diphenylammonium triflate (DPAT) as catalyst makes this protocol cost-effective, low corrosive and easy to handle. Graphic abstract: [Figure not available: see fulltext.].
Passerini/tsuji–trost strategy towards pyrrole derivatives
Narboni, Noisette,El Kaim, Laurent
supporting information, p. 4242 - 4246 (2018/08/28)
The Passerini reaction of α,β-unsaturated aldehydes affords suitable substrates for a Tsuji–Trost reaction with NH-enamines. The latter behave as a 1,3-bisnucleophile, which leads to the formation of pyrrole derivatives with five points of diversity through a Tsuji–Trost/Michael addition/aromatization cascade.
Tandem Copper-Catalyzed Propargylation/Alkyne Azacyclization/Isomerization Reaction under Microwave Irradiation: Synthesis of Fully Substituted Pyrroles
Zhang, Xiao-Yan,Yang, Zhi-Wei,Chen, Zhongzhu,Wang, Jun,Yang, Dong-Lin,Shen, Ze,Hu, Li-Li,Xie, Jian-Wu,Zhang, Jin,Cui, Hai-Lei
, p. 1778 - 1785 (2016/03/15)
A copper-catalyzed and microwave-assisted synthesis of fully substituted pyrroles has been developed. A series of pentasubstituted pyrroles, especially α-arylpyrroles, could be obtained in moderate to good yields (up to 93%) through a tandem propargylation/alkyne azacyclization/isomerization sequence from readily available β-enamino compounds and propargyl acetates.
Solvent-free synthesis of β-enamino ketones and esters catalysed by recyclable iron(III) triflate
Feng, Cheng-Liang,Chu, Ning-Ning,Zhang, Shu-Guang,Cai, Jin,Chen, Jun-Qing,Hu, Hua-You,Ji, Min
, p. 1097 - 1103 (2014/05/20)
A novel application of highly stable Fe(OTf)3 as an efficient catalyst for the synthesis of a variety of β-enamino ketones and esters under solvent-free conditions is described. Notably, this protocol of a "green synthesis", which produced β-enamino ketones and esters by the reaction of a variety of β-dicarbonyl compounds and primary amines, exhibits attractive properties including high yields, short reaction periods, lower loading of catalyst and chemo- and regio-selectivity. In addition, the catalyst was easily recovered from the reaction system and readily reused with minimal loss of activity.
Isoquinolin-1(2H)-ones and 1,6-naphthyridin-5(6H)-ones by an N-acylation-SNAr sequence
Bunce, Richard A.,Nammalwar, Baskar,Gnanasekaran, Krishna Kumar,Cain, Nicholas R.
, p. 838 - 844 (2014/01/23)
A new synthesis of 2,3-dialkyl-4-carbomethoxyisoquinolin-1(2H)-ones and 6,7-dialkyl-8-carbomethoxy-1,6-naphthyridin-5(6H)-ones is reported. The process involves treatment of a β-enaminoester with 2-fluoro-5-nitrobenzoyl chloride, 2-fluorobenzoyl chloride or 2-chloronicotinoyl chloride followed by heating in the presence of base. The conversion, which proceeds by an N-acylation-SNAr reaction sequence, affords 50-86% yields when R 1 is n-alkyl but ≤30% yields when R1 is α-branched.
A general and efficient method for synthesis of enaminones and enamino esters catalyzed by NbCl5 under solvent-free conditions
Liu, Yu-Heng,Wang, Ping,Cheng, Gui-Tian
, p. 191 - 196 (2013/07/27)
A general and simple procedure was developed for the synthesis of β-enaminones and β-enamino esters by reacting 1,3-dicarbonyl compounds with amines in the presence of catalytic amounts of niobium pentachloride. The reaction proceeds smoothly at room temperature under solvent-free conditions and leads to chemo- and regioselective formation of enamine derivatives in high to excellent yields.
Vanadium(IV) acetylacetonate catalyzed stereoselective synthesis of β-enaminoesters and β-enaminones
Laskar, Rajibul A.,Begum, Naznin A.,Hedayetullah Mir, Mohammad,Ali, Shahzad,Khan, Abu T.
, p. 436 - 440 (2013/02/23)
An efficient and stereoselective procedure has been described for the synthesis of a series of β-enaminoesters and β-enaminones by vanadium(IV) acetylacetonate [VO(acac)2] catalyzed reaction of β-ketoesters and 1,3-diketones with both aliphatic and aromatic amines. X-ray crystallographic studies of some representative compounds corroborate two types of structural geometry formed by inter-molecular as well as intra-molecular hydrogen bonds.
Zinc triflate catalysed synthesis of β-enamino ketones(esters) under solvent-free conditions
Feng, Chengliang,Zhang, Shuguang,Cai, Jin,Chen, Junqing,Hu, Huayou,Ji, Min
, p. 626 - 629 (2013/11/06)
An efficient and mild procedure is described for the synthesis of a series of β-enamino ketones(esters) from 1,3-dicarbonyl compounds and aliphatic and aromatic amines using zinc triflate as the catalyst.
Ca(CF3COO)2: An efficient Lewis acid catalyst for chemo- and regio-selective enamination of β-dicarbonyl compounds
Harrad, Mohamed Anoir,Outtouch, Rachid,Ait Ali, Mustapha,Firdoussi, Larbi El,Karim, Abdallah,Roucoux, Alain
scheme or table, p. 442 - 446 (2010/11/21)
A relevant procedure has been developed for the synthesis of β-enaminoesters catalysed by Ca(CF3COO)2. The reaction of β-ketoesters with primary amines was efficiently carried out under solvent-free conditions at room temperature and led to chemo- and regio-selective formations of enamine derivatives in high yields.
