Electroreductive synthesis of polyfunctionalized pyridin-2-ones from acetoacetanilides and carbon disulfide with oxygen evolution

被引：13

作者：

Xu, Lichun ^{[1
]}

Ma, Zhongxiao ^{[1
]}

Hu, Xi ^{[1
]}

Zhang, Xin ^{[1
]}

Gao, Shulin ^{[1
]}

Liang, Deqiang ^{[1
]}

Wang, Baoling ^{[1
]}

Li, Weili ^{[1
]}

Li, Yanni ^{[1
]}

机构：

[1] Kunming Univ, Sch Chem & Chem Engn, Kunming 650214, Yunnan, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 05期

基金：

中国国家自然科学基金;

关键词：

C-H FUNCTIONALIZATION; N-ALLYL ANILINES; METAL-FREE; ALKENES; ELECTROCHEMISTRY; 2-PYRIDONES; CYCLIZATION; CLEAVAGE; PHENOLS; ACCESS;

D O I：

10.1039/d1ob02379a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chemical reductant or a sacrificial electron donor is required in any reduction reactions, generally resulting in undesired chemical waste. Herein, we report a reductant-free reductive [3 + 2 + 1] annulation of beta-keto amides with CS2 enabled by the synergy of electro/copper/base using water as an innocuous anodic sacrifice with O-2 as a sustainable by-product. This electrochemical protocol is mild and provides access to polyfunctionalized pyridin-2-ones from simple starting materials in a single step.

引用

页码：1013 / 1018

页数：6

共 50 条

[1] Vinylogous Blaise Reaction: Conceptually New Synthesis of Pyridin-2-ones
Rao, H. Surya Prakash
Muthanna, Nandurka
Padder, Ashiq Hussain
SYNLETT, 2018, 29 (12) : 1649 - 1653
[2] Novel pirfenidone analogues: Synthesis of pyridin-2-ones for the treatment of pulmonary fibrosis
Ammar, Yousry A.
Ismail, Magda M. F.
El-Sehrawi, Hend M.
Noaman, Eman
Bayomi, Ashraf H.
Shawer, Taghreed Z.
ARCHIV DER PHARMAZIE, 2006, 339 (08) : 429 - 436
[3] Synthesis of Fused 2Н-Pyridin-2-ones under the Conditions of Multicomponent Hantzsch Reaction
I. V. Strashilina
E. M. Arzyamova
O. V. Fedotova
Russian Journal of Organic Chemistry, 2018, 54 : 1173 - 1178
[4] Synthesis of disubstituted imidazo[4,5-b]pyridin-2-ones
Kuethe, JT
Wong, A
Davies, IW
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22): : 7752 - 7754
[5] Regiospecific synthesis of disubstituted pyridin-2-ones and trisubstituted phenols with vinamidinium salts
Jameleddine, Khiari
Thouraya, Gmiza
Adnen, Hadj Ayed Med
Bechir, Ben Hassine
SYNTHETIC COMMUNICATIONS, 2007, 37 (22-24) : 3939 - 3944
[6] Synthesis and evaluation of the antitumor activity of highly functionalised pyridin-2-ones and pyrimidin-4-ones
Du, Xuan-Xuan
Huang, Rong
Yang, Chang-Long
Lin, Jun
Yan, Sheng-Jiao
RSC ADVANCES, 2017, 7 (64) : 40067 - 40073
[7] Solid phase synthesis of 1,3,5-trisubstituted pyridin-2-ones
Linn, JA
Gerritz, SW
Handlon, AL
Hyman, CE
Heyer, D
TETRAHEDRON LETTERS, 1999, 40 (12) : 2227 - 2230
[8] Tetrabutylammonium pyridin-2-olate:: A new reagent for the efficient synthesis of N-aryl pyridin-2-ones
Zhang, Huiping
Chen, Bang-Chi
Wang, Bei
Chao, Sam T.
Zhao, Rulin
Lim, Ngiapkie
Balasubramanian, Balu
SYNTHESIS-STUTTGART, 2008, (10): : 1523 - 1526
[9] SYNTHESIS OF 1,3-DITHIOLO[4,5-C]PYRIDIN-2-ONES
SIPYAGIN, AM
PALTSUN, SV
PIYUK, AV
SVESHNIKOV, NN
KOZLOVSKII, VI
ALIEV, ZG
ZHURNAL ORGANICHESKOI KHIMII, 1993, 29 (09): : 1872 - 1877
[10] SYNTHESIS AND TRANSFORMATIONS OF "4-NITROIMIDAZO[4,5-E]PYRIDIN-2-ONES
YUTILOV, YM
SVERTILOVA, IA
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1986, (01): : 97 - 102

← 1 2 3 4 5 →