Ruthenium-Catalyzed Switchable N-H/C-H Alkenylation of 6-Phenyl(dihydro)pyridazinones with Alkynes

被引：15

作者：

Wang, Wei ^{[1
]}

Liang, Lei ^{[1
]}

Xu, Fengrong ^{[1
]}

Huang, Wenjie ^{[1
]}

Niu, Yan ^{[1
]}

Sun, Qi ^{[1
]}

Xu, Ping ^{[1
]}

机构：

[1] Peking Univ, Dept Med Chem, Sch Pharmaceut Sci, Hlth Sci Ctr, Beijing 100191, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 31期

基金：

中国国家自然科学基金; 高等学校博士学科点专项科研基金;

关键词：

Nitrogen heterocycles; Alkenylation; Alkynes; Ruthenium; Switchable reactions; INTRAMOLECULAR HYDROAMINATION; INTERMOLECULAR HYDROAMINATION; REGIOSELECTIVE HYDROAMINATION; PYRIDAZINONE DERIVATIVES; BOND FUNCTIONALIZATION; ANTIPLATELET ACTIVITY; CARDIOTONIC AGENTS; POTENT; HYDROARYLATION; ALKENES;

D O I：

10.1002/ejoc.201402986

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A ruthenium-catalyzed switchable N-H/C-H alkenylation reaction of 6-phenyl-(dihydro) pyridazin-3(2H)-ones triggered by a nitrogen/oxygen atmosphere was developed. To achieve switchable modification of the two important sites of the widely used pharmacophore, a simple and efficient procedure containing two optimized ruthenium catalytic systems was utilized, which afforded excellent activity, high selectivity, and good tolerance of a wide range of functional groups.

引用

页码：6863 / 6867

页数：5

共 50 条

[1] Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds
Ackermann, Lutz
Lygin, Alexander V.
Hofmann, Nora
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) : 6379 - 6382
[2] Ruthenium-catalyzed C-H/O-H and C-H/N-H bond functionalizations: oxidative annulations of cyclopropyl-substituted alkynes
Deponti, Monica
Kozhushkov, Sergei I.
Yufit, Dmitry S.
Ackermann, Lutz
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (01) : 142 - 148
[3] Ruthenium-catalyzed oxidative C-H alkenylation of aryl carbamates
Li, Jie
Kornhaass, Christoph
Ackermann, Lutz
CHEMICAL COMMUNICATIONS, 2012, 48 (92) : 11343 - 11345
[4] Ruthenium-Catalyzed C-H Amidation and Alkenylation of Cyclic N-Sulfonyl Ketimines
Manoharan, Ramasamy
Jeganmohan, Masilamani
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (23) : 4013 - 4019
[5] Ruthenium-Catalyzed C-H Arylation and Alkenylation of Furfural Imines with Boronates
Siopa, Filipa
Cladera, Valerie-Anne Ramis
Mateus Afonso, Carlos Alberto
Oble, Julie
Poli, Giovanni
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (44) : 6101 - 6106
[6] DFT Case Study on the Comparison of Ruthenium-Catalyzed C-H Allylation, C-H Alkenylation, and Hydroarylation
Zhang, Lei
Wang, Ling-Ling
Fang, De-Cai
ACS OMEGA, 2022, 7 (07): : 6133 - 6141
[7] Ruthenium catalyzed oxidative annulation with alkynes via cascade C-H/N-H bond functionalizations
Wang, Rui
Falck, J. R.
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2014, 759 : 33 - 36
[8] Ruthenium-Catalyzed Synthesis of Macrocyclic Isoquinolines and Isoquinolones via a C-H/N-H Annulations Reaction
Gurumurthy, Palanivelu
Raja, Rajini
Arumugam, Natarajan
Almansour, Abdulrahman I.
Kumar, Raju Suresh
Perumal, Karthikeyan
Parthasarathy, Kanniyappan
CHEMISTRYSELECT, 2023, 8 (32):
[9] Ruthenium-Catalyzed Regioselective C-H Alkenylation Directed by a Free Amino Group
Suzuki, Chiharu
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
ORGANIC LETTERS, 2013, 15 (15) : 3990 - 3993
[10] Ruthenium-Catalyzed Decarboxylative C-H Alkenylation in Aqueous Media: Synthesis of Tetrahydropyridoindoles
Jin, Xiao-Yang
Xie, Li-Jun
Cheng, Hou-Ping
Liu, An-Di
Li, Xue-Dong
Wang, Dong
Cheng, Liang
Liu, Li
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (14): : 7514 - 7522

← 1 2 3 4 5 →