20964-95-8Relevant academic research and scientific papers
Interplay between steric and electronic factors in determining the strength of intramolecular N-H...O resonance-assisted hydrogen bonds in β-enaminones
Bertolasi, Valerio,Pretto, Loretta,Ferretti, Valeria,Gilli, Paola,Gilli, Gastone
, p. 1112 - 1120 (2006)
The crystal structures of five β-enaminones are reported: (2Z)-3-(benzylamino)-1,3-diphenyl-prop-2-en-1-one, (2Z)-3-(benzylamino)-3-(2- hydroxyphenyl)-1-phenyl-prop-2-en-1-one, (2Z)-3-(benzylamino)-3-(4- methoxyphenyl)-1-(3-nitrophenyl)-prop-2-en-1-one, 2
The reaction of β-enaminoesters with organolithium reagents: A convenient method for the regioselective synthesis of enaminoketones
Cimarelli, Cristina,Palmieri, Gianni,Volpini, Emanuela
, p. 6629 - 6631 (2004)
A simple and practical method for the regioselective preparation of β-enaminoketones is described. The method relies on the reaction of β-enaminoesters with organolithium reagents, and allows the preparation of a range of unusual β-enaminoketones.
Regioselective competitive synthesis of 3,5-bis(het) aryl pyrrole-2-carboxylates/carbonitriles vs. β-enaminones from β-thioxoketones
Sharath Kumar, Kothanahally S.,Ananda, Hanumappa,Rangappa, Shobith,Raghavan, Sathees C.,Rangappa, Kanchugarakoppal S.
supporting information, (2021/09/28)
An easily adaptable protocol for the synthesis of 3,5-bis(het)aryl-2-carboxylate/nitrile pyrroles and the related 2,3,5-tri(het)aryl-pyrroles with complementary regioselectivity from the corresponding 1,3-bis(het)aryl-1,3-monothio diketones or β-enaminone precursors has been reported. Initially, regioselective base catalyzed condensation of glycine ethyl/methyl esters or aminoacetonitrile with 1,3-bis(het)aryl-1,3-monothio diketones give β-enaminones, which then in-situ undergoes cyclization to form 3,5-bis(het)aryl-2-carboxylate/nitrile pyrroles. The synthesis of 2,3,5 tri substituted pyrroles with full control over 3rd & 5th position on pyrrole ring is the noteworthy feature of this protocol. Although the product yields are moderate to good, the method offers a facile regioselective entry to 2,3,5 trisubstituted pyrroles without the aid of transition metal.
Trisulfur-Radical-Anion-Triggered C(sp2)-H Amination of Electron-Deficient Alkenes
Nguyen, Khang X.,Nguyen, Thao T.,Nguyen, Tung T.,Pham, Hoai T. B.,Pham, Phuc H.,Phan, Nam T. S.,Wang, Haobin,Yang, Chou-Hsun
supporting information, p. 9751 - 9756 (2020/12/21)
A trisulfur-radical-anion (S3˙-)-triggered C(sp2)-H amination of α,β-unsaturated carbonyl derivatives with simple amines has been demonstrated. This protocol provides convenient access to a variety of synthetically valuable N-unprotected and secondary β-enaminones with absolute Z selectivity and tertiary β-enaminones with E selectivity. Mechanistic probe and electronic structure theory calculations suggest that S3˙- initiates the nucleophilic attacks via a thiirane intermediate.
Metal-Free Method for Direct Synthesis of Functionalized β-Ketoenamines
Zeng, Xiaobao,Liu, Chulong,Yang, Weiguang,Weng, Yunxiang,Wang, Xinyan,Hu, Yuefei
, p. 3656 - 3661 (2019/03/20)
A new method for direct synthesis of β-ketoenamines was developed by a BF3·OEt2-catalyzed cyclization of 1-iodoalkyne and α-keto acid followed by an amine-mediated ring-opening in one pot. Its metal-free conditions allowed the easy synthesis of those products bearing the transition metal-sensitive functional groups. Its three-component process achieved wide range of functionalized products.
Diversity-oriented four-component synthesis of solid state luminescent difluoro oxazaborinines
Dohe, Janis,Ko?mann, Janina,Müller, Thomas J.J.
, p. 198 - 217 (2018/05/22)
(Hetero)aroyl chlorides, alkynes, anilines, and BF3 diethyl etherate are reacted in an alkynylation-amination-cyclization one-pot process to give trisubstituted difluoro oxazaborinines in moderate to very good yield in the sense of a consecutiv
Iron-Catalyzed Synthesis of Substituted Thiazoles from Enamines and Elemental Sulfur through C?S Bond Formation
Wu, Mingzhong,Jiang, Yong,An, Zhenyu,Qi, Zhenjie,Yan, Rulong
supporting information, p. 4236 - 4240 (2018/09/20)
An atom economical approach for the synthesis of substituted thiazoles starting from enamines and elemental sulfur through the C?H functionalization/C?S bond formation is described. Under the optimized conditions, various substituted enamines reacted smoothly with elemental sulfur and the desired substituted thiazoles were generated in moderate to excellent yields. (Figure presented.).
Nano-SiO2 catalyzed synthesis of β-enaminones under solvent free conditions
Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Sarkati, Malihe Norouzi,Zare, Mahboobe
, p. 1591 - 1596 (2016/08/16)
Nano-SiO2 efficiently catalyzed the synthesis of β-enaminones using direct condensation of various (cyclic and acyclic) β-diketones with aromatic and aliphatic amines under solvent-free conditions. This eco-friendly catalyst can be recovered and reused without significant loss of activity. This methodology provides a simple synthetic route to enaminones in excellent yields at room temperature. Graphical abstract: [Figure not available: see fulltext.]
Four-component synthesis of β-enaminone and pyrazole through phosphine-free palladium-catalyzed cascade carbonylation
Shi, Lijun,Xue, Liqin,Lang, Rui,Xia, Chungu,Li, Fuwei
, p. 2560 - 2566 (2015/04/14)
The carbonylative domino synthesis of enaminones and pyrazoles has been performed with the N?N bidentate palladium catalyst to achieve excellent selectivity. These results have confirmed that the carbonylative Sonogashira coupling of iodobenzenes with ter
Regioselective synthesis of β-Aryl enaminones and 1,4,5-trisubstituted 1,2,3-triazoles from chalcones and benzyl azides
Xie, Yu-Yang,Wang, Ying-Chun,Qu, Hong-En,Tan, Xian-Chun,Wang, Heng-Shan,Pan, Ying-Ming
supporting information, p. 3347 - 3355 (2015/02/02)
A highly regioselective synthesis of β-aryl enaminones and 1,4,5-trisubstituted 1,2,3-triazoles from chalcones and benzyl azides based on reaction solvent selection is reported. In the presence of a catalytic amount of Ce (OTf)3, reactions of chalcones with benzyl azides in DMF at 100 °C afforded densely substituted Z-β-aryl enaminones in good to excellent yields, whereas treatment of chalcones with benzyl azides in toluene at 100 °C selectively produced 1,4,5-trisubstituted 1,2,3-triazoles in excellent yields.
