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.
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.
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.
