1149-24-2Relevant articles and documents
Reductive amination of aldehydes and ketones by a Hantzsch dihydropyridine using scandium triflate as a catalyst
Itoh, Takashi,Nagata, Kazuhiro,Kurihara, Ayako,Miyazaki, Michiko,Ohsawa, Akio
, p. 3105 - 3108 (2002)
Direct reductive amination of aldehydes and ketones was carried out using a Hantzsch dihydropyridine as a reducing agent in the presence of a catalytic amount of a Lewis acid.
Photoinduced Aromatization of Dihydropyridines
Lu, Zheng,Yang, Yong-Qing,Li, Hong-Xia
, p. 4221 - 4227 (2016)
The combination of tris(bipyridine)ruthenium(II)/visible light/air is found to be effective for the aromatization of many dihydropyridines. A low catalyst loading of just 0.02 mol% is required.
Histidine-Specific Peptide Modification via Visible-Light-Promoted C-H Alkylation
Chen, Xiaoping,Ye, Farong,Luo, Xiaosheng,Liu, Xueyi,Zhao, Jie,Wang, Siyao,Zhou, Qingqing,Chen, Gong,Wang, Ping
, p. 18230 - 18237 (2019)
Histidine (His) carries a unique heteroaromatic imidazole side chain and plays irreplaceable functional roles in peptides and proteins. Existing strategies for site-selective histidine modification predominantly rely on the N-substitution reactions of the moderately nucleophilic imidazole group, which inherently suffers from the interferences from lysine and cysteine residues. Chemoselective modification of histidine remains one of the most difficult challenges in peptide chemistry. Herein, we report peptide modification via radical-mediated chemoselective C-H alkylation of histidine using C4-alkyl-1,4-dihydropyridine (DHP) reagents under visible-light-promoted conditions. The method exploits the electrophilic reactivity of the imidazole ring via a Minisci-type reaction pathway. This method exhibits an exceptionally broad scope for both peptides and DHP alkylation reagents. Its utility has been demonstrated in a series of important peptide drugs, complex natural products, and a small protein. Distinct from N-substitution reactions, the unsubstituted nitrogen groups of the modified imidazole ring are conserved in the C-H alkylated products.
The Aromatization of Hantzsch Dihydropyridines with Nitric Oxide (NO)
Itoh, Takashi,Nagata, Kazuhiro,Okada, Mamiko,Ohsawa, Akio
, p. 2269 - 2272 (1995)
Hantzsch dihydropyridines were readily oxidized by nitric oxide to give corresponding pyridines in quantitative yields.This reaction system required no work-up procedure.In the presence of oxygen, it was possible to reduce nitric oxide to less than an equ
Dealkenylative Ni-Catalyzed Cross-Coupling Enabled by Tetrazine and Photoexcitation
Cao, Yuhui,Che, Jinteng,Chen, Han,Chen, Si-Cong,Fang, Xianhe,Guo, Yinliang,Guo, Zhixian,Kong, Lingran,Li, Chen,Lu, Jia-Tian,Luo, Tuoping,Zhang, Nan,Zhu, Qi
supporting information, p. 14046 - 14052 (2021/09/13)
A new and general method to functionalize the C(sp3)-C(sp2) bond of alkyl and alkene linkages has been developed, leading to the dealkenylative generation of carbon-centered radicals that can be intercepted to undergo Ni-catalyzed C(sp3)-C(sp2) cross-coupling. This one-pot protocol leverages the easily procured alkene feedstocks for organic synthesis with excellent functional group compatibility without the need for a photoredox catalyst.
Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis
Chiba, Shunsuke,Li, Haoyu,Liu, Yuliang
supporting information, p. 6264 - 6267 (2021/07/02)
A protocol for anti-Markovnikov hydroarylation of alkenes with aryl halides has been developed using polysulfide anions as photocatalysts in the presence of the Hantzsch ester and water under irradiation with visible light.