Gold(iii)-catalyzed chemoselective annulations of anthranils with N-allylynamides for the synthesis of 3-azabicyclo[3.1.0]hexan-2-imines DOI

Lina Song,

Xianhai Tian, Matthias Rudolph

et al.

Chemical Communications, Journal Year: 2019, Volume and Issue: 55(61), P. 9007 - 9010

Published: Jan. 1, 2019

We herein report the gold(iii)-catalyzed selective annulation of anthranils with N-allylynamides under mild conditions.

Language: Английский

Base-Mediated [3 + 4]-Cycloaddition of Anthranils with Azaoxyallyl Cations: A New Approach to Multisubstituted Benzodiazepines DOI
Juan Feng,

Meng Zhou,

Xuanzi Lin

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(16), P. 6245 - 6248

Published: Aug. 1, 2019

A new [3 + 4] cycloaddition of azaoxyallyl cations and anthranils has been achieved for rapid access to multisubstituted benzodiazepine derivatives. variety α-halo hydroxamates were both effective substrates with simple operations under transition-metal-free conditions. The intriguing features this method include its mild nature the reaction conditions, high efficiency, broad substrate scope, wide functional group compatibility.

Language: Английский

Citations

52

Zinc‐Catalyzed Asymmetric Formal [4+3] Annulation of Isoxazoles with Enynol Ethers by 6π Electrocyclization: Stereoselective Access to 2H‐Azepines DOI
Xin‐Qi Zhu, Ze‐Shu Wang,

Bo‐Shang Hou

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 59(4), P. 1666 - 1673

Published: Nov. 14, 2019

6π electrocyclization has attracted interest in organic synthesis because of its high stereospecificity and atom economy the construction versatile 5-7-membered cycles. However, examples asymmetric are quite scarce, have to rely on use chiral organocatalysts, been limited pentadienyl-anion- triene-type electrocyclizations. Described herein is a zinc-catalyzed formal [4+3] annulation isoxazoles with 3-en-1-ynol ethers via electrocyclization, leading site-selective functionalized 2H-azepines 4H-azepines good excellent yields broad substrate scope. Moreover, this strategy also used produce enantioselectivities (up 97:3 e.r.). This protocol not only first heptatrienyl-cation-type but reaction alkynes catalysis based ynol ethers.

Language: Английский

Citations

52

Simple and scalable electrochemical synthesis of 2,1-benzisoxazoles and quinoline N-oxides DOI
Eduardo Rodrigo, Haralds Baunis, Edgars Sūna

et al.

Chemical Communications, Journal Year: 2019, Volume and Issue: 55(81), P. 12255 - 12258

Published: Jan. 1, 2019

Cathodic reduction of the nitro moiety and subsequent intramolecular cyclization affords different substituted 2,1-benzisoxazoles quinoline N-oxides. This methodology allows synthesis two types heterocycles from common simple starting materials, using electrons as a sole reagent for this transformation. The electrolysis can be conducted in very undivided cell under constant current conditions. permits working on larger scale compared to other electrochemical methodologies represents significant advantage.

Language: Английский

Citations

49

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles DOI
Clarice A. D. Caiuby, Matheus Pereira de Jesus, Antonio C. B. Burtoloso

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(11), P. 7433 - 7445

Published: April 28, 2020

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) provide 2-substituted indoles (up 70% yield) just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride dimethylsulfoxonium methylide (23 new examples 45-85% or imino group formation corresponding β-keto anilines presence TiCl4 a Lewis acid (9 33-94% yield).

Language: Английский

Citations

48

Gold(iii)-catalyzed chemoselective annulations of anthranils with N-allylynamides for the synthesis of 3-azabicyclo[3.1.0]hexan-2-imines DOI

Lina Song,

Xianhai Tian, Matthias Rudolph

et al.

Chemical Communications, Journal Year: 2019, Volume and Issue: 55(61), P. 9007 - 9010

Published: Jan. 1, 2019

We herein report the gold(iii)-catalyzed selective annulation of anthranils with N-allylynamides under mild conditions.

Language: Английский

Citations

44