5722-91-8Relevant academic research and scientific papers
Catalyst-free facile and efficient one-pot synthesis of densely functionalized pyrroles and α-amino ketones
Vanga, Sivarama Krishna Reddy,Bollikolla, Hari Babu,Peruri, V. V. Satyanarayana
supporting information, p. 892 - 899 (2021/02/01)
An efficient catalyst-free one-pot three-component synthesis of penta-substituted pyrroles has been successfully developed. A variety of penta-substituted pyrroles were straightforwardly synthesized from good to excellent yields (78%–93%) by using easily
Br?nsted Base-Catalyzed Formal Reductive [3+2] Annulation of 4,4,4-Trifluorocrotonate and α-Iminoketones
Kondoh, Azusa,Terada, Masahiro
, p. 585 - 588 (2020/12/07)
A formal reductive [3+2] annulation of 4,4,4-trifluorocrotonate and α-iminoketones was developed under Br?nsted base catalysis. A single phosphazene base efficiently catalyzes the one-pot tandem reaction involving two mechanistically different elementary processes, namely the chemoselective reduction of an imine moiety of α-iminoketones with thiols as the reductant and the subsequent intermolecular Michael addition of an enolate of α-aminoketones concomitant with lactam formation. This operationally simple method provides β-trifluoromethyl-substituted γ-lactams with a tetrasubstituted carbon as a single diastereomer.
Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME
Zhao, Xinxin,Li, Bing,Xia, Wujiong
supporting information, p. 1056 - 1061 (2020/02/15)
Herein, we describe a visible light-promoted hydroacylation strategy that facilitates the preparation of ketones from alkenes and 4-acyl-1,4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives. In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence of NiCl2·DME.
Synthesis and lung cancer cell line study of pyrrolo[2,3-d]pyrimidine analogs
Dholakia, Sandip P.,Kanada, Kaushik B.,Sureja, Dipen K.,Patel, Jitendra S.
, p. 367 - 372 (2020/01/03)
Three series of new pyrrolo[2,3-d]pyrimidines having diverse groups at position C4 and N7 of the pyrrolo[2,3-d]pyrimidine core were synthesized and their cell line study on the National Cancer Institute (NCI) H1 299 lung cancer cell line was performed. The details of the synthetic methods and characterization data of the synthesized compounds have been presented in this study. Compounds 08a, 08h, 08j, 09h, 09i, 09j, 09m, 09n, and 09o showed excellent anticancer activity compared to standard doxorubicin half maximal inhibitory concentration value on NCI H1 299 (lung cancer cell line) which was nontoxic to normal Vero cell line.
ORGANIC LUMINOGENS
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Page/Page column 38, (2018/12/14)
Small molecule compounds having aggregation-induced emission (AIE) characteristics. The compounds include organic, aromatic salts having anion-π+ interactions. In some embodiments, the anion-π+ interactions can include heavy-atom-ani
Selective synthesis of 1,4,5-trisubstituted imidazoles from α-imino ketones prepared by N-heterocyclic-carbene-catalyzed aroylation
Takashima, Ryo,Tsunekawa, Kaoru,Shinozaki, Maki,Suzuki, Yumiko
, p. 2261 - 2267 (2018/04/02)
An alternative synthetic route to 1,4,5-trisubstituted imidazoles from α-imino ketone, which can be prepared from imidoyl chlorides and aromatic aldehydes via N-heterocycle carbene-catalyzed aroylation was developed. This methodology consists of simple tr
The Acceleration of the Rearrangement of α-Hydroxy Aldimines by Lewis or Bronsted Acids
Zhang, Xin,Dai, Yijing,Wulff, William D.
, p. 2015 - 2018 (2018/09/18)
An efficient method was developed for the synthesis of α-amino ketones from α-hydroxy imines. The reaction occurs through an α-iminol rearrangement involving the migration of a substituent of the carbinol carbon to the imine carbon. The optimal catalysts were found to be silica gel or montmorillonite K 10, which effected migration of a variety of aryl and alkyl substituents in high yields. The rearrangement can also be carried out on imines generated in situ from aldehydes and amines in essentially the same yields as those from the preformed imines.
Coupling of Sulfoxonium Ylides with Arynes: A Direct Synthesis of Pro-Chiral Aryl Ketosulfoxonium Ylides and Its Application in the Preparation of α-Aryl Ketones
Talero, Alexánder Garay,Martins, Bruna Sim?es,Burtoloso, Antonio C. B.
, p. 7206 - 7211 (2018/11/23)
A general, mild, and versatile synthesis of the challenging α-aryl-β-ketosulfoxonium ylides has been developed for the first time, substituting traditional methods starting from diazo compounds. The arylation of easily accessible β-ketosulfoxonium ylides using aryne chemistry allowed the preparation of a large scope of the pro-chiral ylides in very good yields (40 examples; up to 85%). As applications, these ylides were smoothly converted into α-aryl ketones after desulfurization in good yields (up to 98%) as well as in other important derivatives.
Ionization and Anion-π+ Interaction: A New Strategy for Structural Design of Aggregation-Induced Emission Luminogens
Wang, Jianguo,Gu, Xinggui,Zhang, Pengfei,Huang, Xiaobo,Zheng, Xiaoyan,Chen, Ming,Feng, Haitao,Kwok, Ryan T. K.,Lam, Jacky W. Y.,Tang, Ben Zhong
supporting information, p. 16974 - 16979 (2017/11/30)
Recent years have witnessed the significant role of anion-π+ interactions in many areas, which potentially brings the opportunity for the development of aggregation-induced emission (AIE) systems. Here, a new strategy that utilized anion-π
Structure-activity relationship study and optimisation of 2-aminopyrrole-1-benzyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile as a broad spectrum metallo-β-lactamase inhibitor
McGeary, Ross P.,Tan, Daniel T.C.,Selleck, Christopher,Monteiro Pedroso, Marcelo,Sidjabat, Hanna E.,Schenk, Gerhard
, p. 351 - 364 (2017/06/19)
A SAR study on derivatives of 2-amino-1-benzyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile 5a revealed that the 3-carbonitrile group, vicinal 4,5-diphenyl and N-benzyl side chains of the pyrrole are important for the inhibitory potencies of these compounds against members representing the three main subclasses of metallo-β-lactamases (MBLs), i.e. IMP-1 (representing the B1 subgroup), CphA (B2) and AIM-1 (B3). Coupling of 5a with a series of acyl chlorides and anhydrides led to the discovery of two N-acylamide derivatives, 10 and 11, as the two most potent IMP-1 inhibitors in this series. However, these compounds are less effective towards CphA and AIM-1. The N-benzoyl derivative of 5a retained potent in vitro activity against each of MBLs tested (with inhibition constants in the low μM range). Importantly, this compound also significantly enhanced the sensitivity of IMP-1, CphA- or AIM-1-producing cell cultures towards meropenem. This compound presents a promising starting point for the development of a universal MBL inhibitor, targeting members of each of the major subgroups of this family of enzymes.
