Direct and Regioselective Monofluorination of N-Protected Pyridone Derivatives using N-Fluorobenzenesulfonimide (NFSI)

被引：17

作者：

Sakurai, Fumie ^{[1
]}

Yukawa, Takafumi ^{[1
]}

Taniguchi, Takahiko ^{[1
]}

机构：

[1] Takeda Pharmaceut Co Ltd, Neurosci Drug Discovery Unit, Drug Discovery Chem Labs, 26-1 Muraoka Higashi 2-Chome, Fujisawa, Kanagawa 2518555, Japan

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 18期

关键词：

FLUORINATING AGENTS; DISCOVERY; INHIBITORS; SALTS; TRIFLUOROMETHYLTHIOLATION; CONSTRUCTION; REACTIVITY; RECEPTOR;

D O I：

10.1021/acs.orglett.9b02482

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct monofluorination of N-protected pyridone derivatives has been developed using a stable electrophilic fluorinating reagent, N-fluorobenzenesulfonimide (NFSI). Interestingly, the fluorine atom is regioselectively introduced at the position opposite the carbonyl group in the pyridone substrate during the reaction. This method is applicable to a wide range of substrates and allows the regioselective late-stage monofluorination of pyridone scaffolds.

引用

页码：7254 / 7257

页数：4

共 7 条

[1] Iodine-Induced Regioselective C-C and C-N Bonds Formation of N-Protected Indoles
Li, Ying-Xiu
Ji, Ke-Gong
Wang, Hai-Xi
Ali, Shaukat
Liang, Yong-Min
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02) : 744 - 747
[2] Direct Transformation of N-Protected α,β-Unsaturated γ-Amino Amides into γ-Lactams through a Base-Mediated Molecular Rearrangement
Kumar, Mothukuri Ganesh
Veeresh, Kuruva
Nalawade, Sachin A.
Nithun, Raj V.
Gopi, Hosahudya N.
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23) : 15145 - 15153
[3] New Synthetic Strategy for High-Enantiopurity N-Protected α-Amino Ketones and their Derivatives by Asymmetric Hydrogenation
Sun, Tian
Hou, Guohua
Ma, Miaofeng
Zhang, Xumu
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) : 253 - 256
[4] Copper-catalyzed O-arylation of N-protected 1,2-aminoalcohols using functionalized trivalent organobismuth reagents
Petiot, Pauline
Dansereau, Julien
Hebert, Martin
Khene, Imene
Ahmad, Tabinda
Samaali, Samira
Leroy, Maxime
Pinsonneault, Francis
Legault, Claude Y.
Gagnon, Alexandre
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (05) : 1322 - 1327
[5] Facile direct synthesis of unsymmetrical ureas from N-Alloc-, N-Cbz-, and N-Boc-protected amines using DABAL-Me3
Kang, Soosung
Kim, Hee-Kwon
TETRAHEDRON, 2018, 74 (30) : 4036 - 4046
[6] A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H
Ivkovic, Jakov
Lembacher-Fadum, Christian
Breinbauer, Rolf
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (42) : 10456 - 10460
[7] Enzymatic preparation of 5-hydroxy-L-proline, N-Cbz-5-hydroxy-L-proline, and N-boc-5-hydroxy-L-proline from (α-N-protected)-L-ornithine using a transaminase or an amine oxidase
Hanson, R. L.
Johnston, R. M.
Goldberg, S. L.
Parker, W. L.
Patel, R. N.
ENZYME AND MICROBIAL TECHNOLOGY, 2011, 48 (6-7) : 445 - 453

← 1 →