21911-68-2Relevant articles and documents
Reaction of Symmetric N1 ,N2-Diarylamidines with α-Bromoacetophenone and Ethyl 2-Bromoethanoate
Gomaa, Mohsen Abdel-Motaal
, p. 654 - 655 (1998)
2-Bromo-1-{aryl[1-(arylimino)ethyl]amino}-1-phenylethanol derivatives 3a, 3b were obtained from the reaction of N1 ,N2-diarylacetamidines 1a, 1b with α-bromoacetophenone 2, while 1a, 1b with ethyl 2-bromoethanoate 4 afforded 2-{[1-(arylimino)]ethyl}aminoethanoic acid derivatives 5a, 5b; N1,N2-diarylformamidines 6a, 6b reacted with 2 and 4 to give the arylaminoacetophenones 8a, 8b and N-arylglycine ethyl esters 11a, 11b respectively together with the corresponding formanilides 9a, 9b.
Synthesis and bioactivity of novel (Z,E)-1-(substituted phenyl)-3-[α -(alkyloxyimino)benzylidene]pyrrolidine-2,4-dione derivatives
Zheng, Xiao-Qian,Han, Bao-Feng,Wang, Xian-Feng,Qiang, Sheng,Yang, Chun-Long
, p. 73 - 78 (2011)
A series of 1-(substituted phenyl)-3-[α-(alkyloxyimino)-benzylidene] pyrrolidine-2,4-dione derivatives as a mixture of two geometrical isomers of Z-configuration and E-configu-ration were synthesized by the reaction of the corresponding α -hydroxybenzylidene analogs with alkyloxyamine hydro-chlorides. The target compounds were confirmed by IR, 1 H NMR, MS and elemental analysis. The title compounds exhibit inhibitory activity against Echinochloa crusgalli and Brassica campestris. Copyright by Walter de Gruyter Berlin Boston.
Insertion of ethyl diazoacetate into N-H and S-H bonds catalyzed by ruthenium porphyrin complexes
Galardon, Erwan,Le Maux, Paul,Simonneaux, Gerard
, p. 2455 - 2456 (1997)
Ruthenium porphyrin complexes catalyze insertion of ethyl diazoacetate into sulfur-hydrogen and nitrogen-hydrogen bonds under mild conditions and with reasonable to very good yields.
Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ
Zheng, Yuanqin,Zhou, Yuqiao,Zhang, Yan,Deng, Pengchi,Zhao, Xiaohu,Jiang, Shichao,Du, Guangxi,Shen, Xin,Xie, Xinyu,Su, Zhishan,Yu, Zhipeng
supporting information, (2021/12/22)
Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.
Perovskite as Recyclable Photocatalyst for Annulation Reaction of N-Sulfonyl Ketimines
Shi, Anzai,Sun, Kai,Chen, Xiaolan,Qu, Lingbo,Zhao, Yufen,Yu, Bing
supporting information, p. 299 - 303 (2022/01/04)
A sustainable and cost-effective manner for the photocatalytic annulation reaction of N-sulfonyl ketimines with N-arylglycines to synthesize imidazolidine-fused sulfamidates (31 examples) by employing CsPbBr3 as a heterogeneous photocatalyst has been developed. The catalyst CsPbBr3 can be simply recovered from the reaction mixture and reused at least five times without an obvious reduction in its photocatalytic reactivity, exhibiting a high catalyst economic feature.
Tunable Redox Potential Photocatalyst: Aggregates of 2,3-Dicyanopyrazino Phenanthrene Derivatives for the Visible-Light-Induced α-Allylation of Amines
Bao, Ming,He, Min,Wang, Yi,Yu, Xiaoqiang
, p. 14720 - 14731 (2021/11/16)
This work highlights the tunable redox potential of 6,11-dibromo-2,3-dicyanopyrazinophenanthrene (DCPP3) aggregates, which can be formed through physical π-πstacking interactions with other DCPP3 monomers. Electrochemical and scanning electron microscopy showed that the reduction potential of [DCPP3]n aggregates could be increased by decreasing their size. The size of [DCPP3]n aggregates could be regulated by controlling the concentration of DCPP3 in an organic solvent. As such, a fundamental understanding of this tunable redox potential is essential for developing new materials for photocatalytic applications. The [DCPP3]n aggregates as a visible-light photocatalyst in combination with Pd catalysts in the visible-light-induced α-allylation of amines were used. This [DCPP3]n photocatalyst exhibits excellent photo- and electrochemical properties, including a remarkable visible-light absorption, long excited-state lifetime (16.6 μs), good triplet quantum yield (0.538), and high reduction potential (Ered([DCPP3]n/[DCPP3]n-) > -1.8 V vs SCE).
Selective carbene transfer to amines and olefins catalyzed by ruthenium phthalocyanine complexes with donor substituents
Cailler, Lucie P.,Kroitor, Andrey P.,Martynov, Alexander G.,Gorbunova, Yulia G.,Sorokin, Alexander B.
supporting information, p. 2023 - 2031 (2021/02/26)
Electron-rich ruthenium phthalocyanine complexes were evaluated in carbene transfer reactions from ethyl diazoacetate (EDA) to aromatic and aliphatic olefins as well as to a wide range of aromatic, heterocyclic and aliphatic amines for the first time. It was revealed that the ruthenium octabutoxyphthalocyanine carbonyl complex [(BuO)8Pc]Ru(CO) is the most efficient catalyst converting electron-rich and electron-poor aromatic olefins to cyclopropane derivatives with high yields (typically 80-100%) and high TON (up to 1000) under low catalyst loading and nearly equimolar substrate/EDA ratio. This catalyst shows a rare efficiency in the carbene insertion into amine N-H bonds. Using a 0.05 mol% catalyst loading, a high amine concentration (1 M) and 1.1 eq. of EDA, a number of structurally divergent amines were selectively converted to mono-substituted glycine derivatives with up to quantitative yields and turnover numbers reaching 2000. High selectivity, large substrate scope, low catalyst loading and practical reaction conditions place [(BuO)8Pc]Ru(CO) among the most efficient catalysts for the carbene insertion into amines.
Visible-Light-Induced Oxidative α-Alkylation of Glycine Derivatives with Ethers under Metal-Free Conditions
Song, Yang,Zhang, Hao,Guo, Jiabao,Shao, Yifei,Ding, Yuzhou,Zhu, Li,Yao, Xiaoquan
, p. 5914 - 5921 (2021/11/22)
In this work, a visible-light-induced oxidative α-alkylation of glycine derivatives with ethers has been developed in the presence of catalytic Eosin Y. Under the blue light of a 3 W LED, a range of α-etherized glycine derivatives, including α-amino esters, α-amino ketones and α-amino amides, were achieved with good to excellent yields and functional group tolerance with tert-butyl hydroperoxide (TBHP) as oxidant at ambient temperature. The operationally easy procedure provides an economical, metal-free, and mild alternative for the synthesis of the α-etherized glycine derivatives.
Photoredox-Catalyzed α-Aminomethyl Carboxylation of Styrenes with Sodium Glycinates: Synthesis of γ-Amino Acids and γ-Lactams
Zhou, Cong,Li, Miao,Sun, Jianwei,Cheng, Jiang,Sun, Song
supporting information, p. 2895 - 2899 (2021/05/05)
A visible-light photoredox-catalyzed reductive α-aminomethyl carboxylation of styrenes with sodium glycinates and CO2 has been developed to synthesize a series of α,α-disubstituted γ-amino acids and γ-lactams with high efficiency and regioselectivity. Notably, CO2 released from the decarboxylation step can be reused for the subsequent carboxylation. Distinct from the previous reactions with the same type of substrates leading to simple decarboxylation and olefin hydroalkylation, this process involves additional CO2 sequestration, thus leading to olefin α-aminomethyl carboxylation. These findings not only provide new access to α,α-disubstituted γ-amino acids and γ-lactams but also serve as a proof of concept for CO2 reutilization in decarboxylation reactions.
Molecular Oxygen-Mediated Radical Alkylation of C(sp3)-H Bonds with Boronic Acids
Yang, Le,Qiu, Zhihong,Wu, Jintao,Zhao, Jianyou,Shen, Tong,Huang, Xuan,Liu, Zhong-Quan
supporting information, p. 3207 - 3210 (2021/05/04)
A direct and site-specific alkylation of (sp3)C-H bond with aliphatic boronic acid was achieved. By simply heating glycinates and amines together with alkylboronic acids under an oxygen atmosphere, a variety of unnatural α-amino acids and peptides could b
