Copper-catalyzed C(sp3)-H functionalization of ketones with vinyl azides: synthesis of substituted-1H-pyrroles

被引：32

作者：

Donthiri, Ramachandra Reddy ^{[1
]}

Samanta, Supravat ^{[1
]}

Adimurthy, Subbarayappa ^{[1
]}

机构：

[1] CSIR, Cent Salt & Marine Chem Res Inst, Acad Sci & Innovat Res Proc Design & Engn Cell, Bhavnagar 364002, Gujarat, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 40期

关键词：

H BOND FUNCTIONALIZATION; PYRROLE SYNTHESIS; 3+2 CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; SUBSTITUTED PYRROLES; OXIDATIVE LINKAGE; C-N; ALKYNES; FACILE; 2H-AZIRINES;

D O I：

10.1039/c5ob01407g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper-catalyzed C(sp(3))-H functionalization of ketones with vinyl azides for the synthesis of substituted pyrroles has been developed. The method is a straightforward and efficient way to access a series of 2,3,5-trisubstituted-1H-pyrroles in modest to excellent yields with broad functional group tolerance under mild conditions.

引用

页码：10113 / 10116

页数：4

共 56 条

[1]

[Anonymous], J MED CHEM

[2] Discovery of a Novel Pyrrole Derivative 1-[5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine Fumarate (TAK-438) as a Potassium-Competitive Acid Blocker (P-CAB) [J].

Arikawa, Yasuyoshi ;

Nishida, Haruyulci ;

Kurasawa, Osamu ;

Hasuoka, Atsushi ;

Hirase, Keizo ;

Inatomi, Nobuhiro ;

Hori, Yasunobu ;

Matsukawa, Jun ;

Imanishi, Akio ;

Kondo, Mitsuyo ;

Tarui, Naoki ;

Hamada, Teruki ;

Takagi, Terufumi ;

Takeuchi, Toshiyuki ;

Kajino, Masahiro .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (09) :4446-4456

[3] Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot Sila-Stetter/Paal-Knorr strategy [J].

Bharadwaj, AR ;

Scheidt, KA .

ORGANIC LETTERS, 2004, 6 (14) :2465-2468

[4] 2,4-vs 3,4-Disubsituted Pyrrole Synthesis Switched by Copper and Nickel Catalysts [J].

Chen, Feng ;

Shen, Tao ;

Cui, Yuxin ;

Jiao, Ning .

ORGANIC LETTERS, 2012, 14 (18) :4926-4929

[5] Synthesis of polysubstituted N-H pyrroles from vinyl azides and 1,3-dicarbonyl compounds [J].

Chiba, Shunsuke ;

Wang, Yi-Feng ;

Lapointe, Guillaume ;

Narasaka, Koichi .

ORGANIC LETTERS, 2008, 10 (02) :313-316

[6] Regioselective synthesis of substituted pyrroles: Efficient palladium-catalyzed cyclization of internal alkynes and 2-amino-3-iodoacrylate derivatives [J].

Crawley, Matthew L. ;

Goljer, Igor ;

Jenkins, Douglas J. ;

Mehlmann, John F. ;

Nogle, Lisa ;

Dooley, Rebecca ;

Mahaney, Paige E. .

ORGANIC LETTERS, 2006, 8 (25) :5837-5840

[7] Copper-Catalyzed C-H Functionalization of Pyridines and Isoquinolines with Vinyl Azides: Synthesis of Imidazo Heterocycles [J].

Donthiri, Ramachandra Reddy ;

Pappula, Venkatanarayana ;

Reddy, N. Naresh Kumar ;

Bairagi, Dipayan ;

Adimurthy, Subbarayappa .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (22) :11277-11284

[8] Recent advances in the synthesis of pyrroles by multicomponent reactions [J].

Estevez, Veronica ;

Villacampa, Mercedes ;

Menendez, J. Carlos .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (13) :4633-4657

[9] Multicomponent reactions for the synthesis of pyrroles [J].

Estevez, Veronica ;

Villacampa, Mercedes ;

Carlos Menendez, J. .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) :4402-4421

[10] Lamellarins and related pyrrole-derived alkaloids from marine organisms [J].

Fan, Hui ;

Peng, Jiangnan ;

Hamann, Mark T. ;

Hu, Jin-Feng .

CHEMICAL REVIEWS, 2008, 108 (01) :264-287

← 1 2 3 4 5 6 →