A General and Mild Palladium-Catalyzed Domino Reaction for the Synthesis of 2H-Indazoles

被引：100

作者：

Halland, Nis ^{[1
]}

Nazare, Marc ^{[1
]}

R'kyek, Omar ^{[1
]}

Alonso, Jorge ^{[1
]}

Urmann, Matthias ^{[1
]}

Lindenschmidt, Andreas ^{[2
]}

机构：

[1] Sanofi Aventis Deutschland GmbH, D-65926 Frankfurt, Germany

[2] Sanofi Aventis Deutschland GmbH, TD Thrombosis & Angiogenesis, D-65926 Frankfurt, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 37期

关键词：

alkynes; domino reactions; homogeneous catalysis; nitrogen heterocycles; palladium; N-ARYLATION; DERIVATIVES; INDAZOLES; HETEROCYCLIZATION; 2-ARYL-2H-INDAZOLES; CYCLIZATION; TRIAZOLES; ADDUCTS; INDOLES;

D O I：

10.1002/anie.200902323

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Practical and highly versatile, the reaction of readily available (2-chlorophenyl)acetylene and hydrazine substrates affords substituted 2H-indazoles in just a few hours under very mild reaction conditions (see scheme; DMF=N,N-dimethylformamide). The catalyzed domino sequence consists of a regioselective coupling followed by an intramolecular hydroamination and subsequent isomerization of the resulting exocyclic bond. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6879 / 6882

页数：4

共 50 条

[1] A Palladium-Catalyzed Domino Reaction To Access 3-Amino-2H-indazoles from Hydrazines and 2-Halobenzonitriles
Alsalim, Rana
Lindemann, Peter
Lopez-Alberca, Maria Pascual
Miksche, Sandra
Czechtizky, Werngard
Halland, Nis
Nazare, Marc
[J]. ORGANIC LETTERS, 2020, 22 (18) : 7393 - 7396
[2] A novel synthesis of 2-aryl-2H-indazoles via a palladium-catalyzed intramolecular amination reaction
Song, JJ
Yee, NK
[J]. ORGANIC LETTERS, 2000, 2 (04) : 519 - 521
[3] Total Synthesis of Linoxepin through a Palladium-Catalyzed Domino Reaction
Tietze, Lutz F.
Duefert, Svenia-C.
Clerc, Jerome
Bischoff, Matthias
Maass, Christian
Stalke, Dietmar
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) : 3191 - 3194
[4] First total synthesis of (±)-Linoxepin via a palladium-catalyzed domino reaction
Schild, Svenia C.
Clerc, Jerme
Tietze, Lutz F.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[5] Palladium-catalyzed enantioselective domino reaction for the efficient synthesis of vitamin E
Tietze, LF
Sommer, KM
Zinngrebe, J
Stecker, F
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (02) : 257 - 259
[6] Synthesis of Annulated 2H-Indazoles and 1,2,3-and 1,2,4-Triazoles via a One-Pot Palladium-Catalyzed Alkylation/Direct Arylation Reaction
Laleu, Benoit
Lautens, Mark
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22): : 9164 - 9167
[7] Synthesis of 2H-indazoles via the Cadogan reaction in batch and flow mode
Duffy, Matilda
Di Filippo, Mara
Baumann, Marcus
[J]. TETRAHEDRON LETTERS, 2021, 86
[8] Synthesis of Tetrasubstituted Alkenes through a Palladium-Catalyzed Domino Carbopalladation/C-H-Activation Reaction
Tietze, Lutz F.
Hungerland, Tim
Duefert, Alexander
Objartel, Ina
Stalke, Dietmar
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (11) : 3286 - 3291
[9] Synthesis of 2-substituted indoles via a palladium-catalyzed domino Heck reaction and dealkylation
Mao, Hui
Wan, Jie-Ping
Pan, Yuanjiang
Sun, Cuirong
[J]. TETRAHEDRON LETTERS, 2010, 51 (14) : 1844 - 1846
[10] Synthesis of Fluorescent Indazoles by Palladium-Catalyzed Benzannulation of Pyrazoles with Alkynes
Kim, Og Soon
Jang, Jin Hyeok
Kim, Hyun Tae
Han, Su Jin
Tsui, Gavin Chit
Joo, Jung Min
[J]. ORGANIC LETTERS, 2017, 19 (06) : 1450 - 1453

← 1 2 3 4 5 →