550-60-7Relevant articles and documents
Specific para-hydroxylation of nitronaphthalenes with cumene hydroperoxide in basic aqueous media
Zhu, Lei,Zhang, Lin-Hua
, p. 3519 - 3522 (2000)
A synthetic method for specific para-hydroxylation of nitroarenes has been developed. The reaction of nitronaphthalenes with cumeme hydroperoxide in basic aqueous media produces exclusively para-hydroxy nitronaphthalenes in good yield. The selectivity of ortho and para hydroxylation is mediated by water content. The rationale for water-controlled orientation of hydroxylation has been briefly discussed. (C) 2000 Elsevier Science Ltd.
Light-Controlled Tyrosine Nitration of Proteins
Long, Tengfang,Liu, Lei,Tao, Youqi,Zhang, Wanli,Quan, Jiale,Zheng, Jie,Hegemann, Julian D.,Uesugi, Motonari,Yao, Wenbing,Tian, Hong,Wang, Huan
supporting information, p. 13414 - 13422 (2021/05/12)
Tyrosine nitration of proteins is one of the most important oxidative post-translational modifications in vivo. A major obstacle for its biochemical and physiological studies is the lack of efficient and chemoselective protein tyrosine nitration reagents. Herein, we report a generalizable strategy for light-controlled protein tyrosine nitration by employing biocompatible dinitroimidazole reagents. Upon 390 nm irradiation, dinitroimidazoles efficiently convert tyrosine residues into 3-nitrotyrosine residues in peptides and proteins with fast kinetics and high chemoselectivity under neutral aqueous buffer conditions. The incorporation of 3-nitrotyrosine residues enhances the thermostability of lasso peptide natural products and endows murine tumor necrosis factor-α with strong immunogenicity to break self-tolerance. The light-controlled time resolution of this method allows the investigation of the impact of tyrosine nitration on the self-assembly behavior of α-synuclein.
Ruthenium-Catalyzed Tandem Carbene/Alkyne Metathesis/N-H Insertion: Synthesis of Benzofused Six-Membered Azaheterocycles
Padín, Damián,Saá, Carlos,Varela, Jesús A.
supporting information, (2020/03/30)
The Cp*RuCl-based catalyst enables expedient access to a variety of benzofused six-membered azaheterocycles from unprotected o-alkynylanilines and trimethylsilyldiazomethane through an unprecedent tandem carbene/alkyne metathesis/N-H insertion reaction. The transformation takes place under mild reaction conditions (room temperature, 15 min) and with excellent functional group tolerance. The synthetic utility of the final products and a mechanistic rationale are also discussed.
Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Br?nsted Acidic NO2+ Generation
Juárez-Ornelas, Kevin A.,Jiménez-Halla, J. Oscar C.,Kato, Terumasa,Solorio-Alvarado, César R.,Maruoka, Keiji
supporting information, p. 1315 - 1319 (2019/03/07)
The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Br?nsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.
