17900-66-2Relevant academic research and scientific papers
Carbamoylation of Azomethine Imines via Visible-Light Photoredox Catalysis
Correia, José Tiago M.,Matsuo, Bianca T.,Oliveira, Pedro H. R.,Paix?o, Márcio W.
supporting information, p. 6775 - 6779 (2021/09/13)
A versatile and robust photocatalytic methodology to install the amide functional group into azomethine imine ions is described. This protocol is distinguished by its broad scope and mild reaction conditions, which are well suited for the preparation of s
Visible-Light-Mediated α-Amino Alkylation of Azomethine Imines: An Approach to N-(β-Aminoalkyl)pyrazolidinones
Matsuo, Bianca T.,Correia, José Tiago M.,Paix?o, Márcio W.
supporting information, p. 7891 - 7896 (2020/11/02)
Herein, a mild and robust photocatalytic protocol for the combination of amino and pyrazolidinone functionalities through a radical α-amino alkylation of azomethine iminium ions is demonstrated. This method presents a high functional group tolerance provi
Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs
Barrow, Andrew S.,Cheng, Yunfei,Gialelis, Timothy L.,Giel, Marie-Claire,Kitamura, Seiya,Li, Gencheng,Moses, John E.,Ottonello, Alessandra,Sharpless, K. Barry,Smedley, Christopher J.,Wolan, Dennis W.
supporting information, p. 12460 - 12469 (2020/06/10)
Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease”, by combining classic C?C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels–Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates—demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.
Br?nsted Acid-Catalyzed (4 + 3) Cyclization of N, N′-Cyclic Azomethine Imines with Isatoic Anhydrides
Li, Can,Wang, Cong-Shuai,Li, Tian-Zhen,Mei, Guang-Jian,Shi, Feng
supporting information, p. 598 - 602 (2019/01/25)
A Br?nsted acid-catalyzed (4 + 3) cyclization of N,N′-cyclic azomethine imines with isatoic anhydrides has been discovered, which constructs seven-membered nitrogenous heterocyclic frameworks with overall high yields (up to 98% yield). This reaction repre
Solvent incorporated sequential [3 + 2] annulation/substitution reaction of azomethine imines and propargyl sulfur ylide
Shen, Shoujie,Yang, Yanli,Duan, Jiangyan,Jia, Zhenhu,Liang, Jinyan
supporting information, p. 1068 - 1072 (2018/02/22)
A novel solvent incorporated sequential [3 + 2] cycloaddition/substitution reaction of azomethine imines with propargyl sulfur ylide was developed. In the actual three-component reaction, propargyl sulfur ylide acts as a dipole reagent to furnish the annu
Chiral Phosphine–Phosphite Ligands in Asymmetric Gold Catalysis: Highly Enantioselective Synthesis of Furo[3,4-d]-Tetrahydropyridazine Derivatives through [3+3]-Cycloaddition
Du, Qingwei,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther
supporting information, p. 2379 - 2383 (2018/01/27)
The AuI-catalyzed reaction of 2-(1-alkynyl)-2-alken-1-ones with azomethine imines regio- and diastereoselectively affords furo[3,4-d]tetrahydropyridazines in a tandem cyclization/intermolecular [3+3]-cycloaddition process under mild conditions.
Asymmetric [3 + 2] Cycloaddition Employing N, N′-Cyclic Azomethine Imines Catalyzed by Chiral-at-Metal Rhodium Complex
Gong, Jun,Wan, Qian,Kang, Qiang
supporting information, p. 3354 - 3357 (2018/06/11)
An efficient asymmetric 1,3-dipolar cycloaddition of α,β-unsaturated 2-acyl imidazoles with N,N′-cyclic azomethine imines catalyzed by a chiral-at-metal rhodium complex is reported. The corresponding N,N′-bicyclic pyrazolidine derivatives with three conti
Bronsted acid or lewis acid catalyzed [3+3] cycloaddition of azomethine imines with N-benzyl azomethine ylide: A facile access to bicyclic N-heterocycles
Li, Shuo-Ning,Yu, Bin,Liu, Jia,Li, Hong-Lian,Na, Risong
supporting information, p. 282 - 286 (2016/01/20)
1,3-Dipolar cycloaddition reactions are one of the most important methods to obtain diverse heterocycles with novel skeletons. We herein report the Bronsted acid or Lewis acid catalyzed [3+3] cycloaddition of azomethine imines with nonstabilized azomethine ylide generated in situ from an N-benzyl precursor, providing a clean and facile access to diverse bicyclic N-heterocycles in moderate to good yields for further biological testing. Also, the protocol developed achieved the formation of C-C and C-N bonds simultaneously in a single step.
Diastereoselective 1,3-Dipolar Cycloadditions of N,N′-Cyclic Azomethine Imines with Iminooxindoles for Access to Oxindole Spiro-N,N-bicyclic Heterocycles
Zhao, Hong-Wu,Li, Bo,Pang, Hai-Liang,Tian, Ting,Chen, Xiao-Qin,Song, Xiu-Qing,Meng, Wei,Yang, Zhao,Zhao, Yu-Di,Liu, Yue-Yang
supporting information, p. 848 - 851 (2016/03/04)
In the presence of CuI, 1,3-dipolar cycloadditions of N,N′-cyclic azomethine imines with iminooxindoles proceeded readily and furnished novel oxindole spiro-N,N-bicyclic heterocycles in moderate to excellent chemical yields with excellent diastereoselecti
[3 + 2]-Cycloadditions of Azomethine Imines and Ynolates
Winterton, Sarah E.,Ready, Joseph M.
supporting information, p. 2608 - 2611 (2016/06/15)
A novel [3 + 2]-cycloaddition between azomethine imines and lithium ynolates is described to synthesize bicyclic pyrazolidinones. These bicyclic pyrazolidinones are versatile intermediates to form β-amino acids and monocyclic pyrazolidinones. High diaster
