Metal-free multicomponent cascade reactions of homopropargylic amines and acyl chlorides as well as potassium thiocyanate and diiodine: an access to thiazine imides

2018 ◽  
Vol 16 (33) ◽  
pp. 5955-5959
Author(s):  
Jing Wu ◽  
Yuanfang Kong ◽  
Lingyan Liu ◽  
Weixing Chang ◽  
Jing Li
Keyword(s):  
Potassium Thiocyanate ◽  
Cascade Reactions ◽  
Cascade Reaction ◽  
Acyl Chlorides ◽  
Metal Free

A novel metal-free multicomponent cascade reaction was developed for the construction of thiazine imides.

Efficient construction of C–N and C–S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate

2017 ◽  
Vol 15 (17) ◽  
pp. 3611-3615 ◽  
Author(s):  
Xue-Bing Chen ◽  
Xue-Quan Wang ◽  
Jia-Na Song ◽  
Qing-Li Yang ◽  
Chao Huang ◽  
...  
Keyword(s):  
Potassium Thiocyanate ◽  
Cascade Reactions ◽  
Cascade Reaction ◽  
Efficient Construction

Regioselective cascade reactions have been developed by using enaminones and potassium thiocyanate, offering a novel protocol for the synthesis of thiazoles from enaminones.

A metal-free yne-addition/1,4-aryl migration/decarboxylation cascade reaction of alkynoates with Csp3–H centers

2016 ◽  
Vol 14 (7) ◽  
pp. 2210-2217 ◽  
Author(s):  
De-Long Kong ◽  
Liang Cheng ◽  
Hong-Ru Wu ◽  
Yang-Xiong Li ◽  
Dong Wang ◽  
...  
Keyword(s):  
Cascade Reaction ◽  
Single Site ◽  
Metal Free ◽  
Different Types

Reactions of alkynoates with different types of radical precursors under metal-free conditions affording single-site-addition poly-substituted alkenes were reported.

A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy phenylacetylenes to assemble diphosphonyl xanthene derivatives

2021 ◽  
Author(s):  
Tao Fan ◽  
Yan Liu ◽  
Caina Jiang ◽  
Yanli Xu ◽  
Yan-Yan Chen
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Cascade Reaction ◽  
Phosphine Oxides ◽  
Metal Free ◽  
Mild Conditions ◽  
Xanthene Derivatives ◽  
Reaction Proceeds ◽  
Radical Cascade

A radical cascade reaction of 2-aryloxy phenylacetylene with phosphine oxides promoted by K2S2O8 was developed, provided diphosphonyl xanthenes as products. This reaction proceeds under transition metal-free and mild conditions with...

Transition Metal-Free Cascade Reactions of Alkynols to Afford Isoquinolin-1(2H)-one and Dihydroisobenzofuran Derivatives

2014 ◽  
Vol 79 (10) ◽  
pp. 4602-4614 ◽  
Author(s):  
Deng Yuan Li ◽  
Ke Ji Shi ◽  
Xiao Feng Mao ◽  
Guo Rong Chen ◽  
Pei Nian Liu
Keyword(s):  
Transition Metal ◽  
Cascade Reactions ◽  
Metal Free

Organophosphane-Catalyzed Construction of Functionalized 2-Ylideneoxindoles via Direct β-Acylation

Synthesis ◽  
2021 ◽  
Author(s):  
Wey-Chyng Jeng ◽  
Po-Chung Chien ◽  
Sandip Sambhaji Vagh ◽  
Athukuri Edukondalu ◽  
Wenwei Lin
Keyword(s):  
Intramolecular Cyclization ◽  
Efficient Method ◽  
Bond Cleavage ◽  
Scale Up ◽  
Acyl Chlorides ◽  
Metal Free ◽  
Mild Conditions ◽  
Synthetic Utility ◽  
Mechanistic Investigations ◽  
Synthetic Transformations

We report an efficient method for the direct β-acylation of 2-ylideneoxindoles with acyl chlorides in the presence of base-catalyzed by organophosphanes. A variety of functionalized 2-ylideneoxindoles were prepared in moderate to good yields under metal-free and mild conditions via a tandem phospha-Michael/O-acylation/intramolecular cyclization/ rearrangement sequence. The mechanistic investigations revealed that the C-O bond cleavage on possible betaine intermediate is the key step for the installation of keto-functionality at β-position of 2-ylideneoxindoles in a highly stereospecific manner. The synthetic utility of this protocol could also be proven by scale-up reactions and synthetic transformations of the products.

A transition-metal-free multicomponent reaction towards constructing chiral 2H-1,4-benzoxazine scaffolds

2020 ◽  
Vol 22 (21) ◽  
pp. 7506-7512
Author(s):  
Lixiang Zhu ◽  
Xiaoyu Ren ◽  
Juan Du ◽  
Jia-Hong Wu ◽  
Jian-Ping Tan ◽  
...  
Keyword(s):  
Transition Metal ◽  
Multicomponent Reaction ◽  
Phosphonium Salt ◽  
Cascade Reaction ◽  
Metal Free

A transition-metal-free multicomponent cascade reaction of α-halogenated ketones, ortho-aminophenols, and aldehydes using a dipeptide phosphonium salt catalyst was developed for the construction of various 2H-1,4-benzoxazines.

De novo synthesis of benzofurans via trifluoroacetic acid catalyzed cyclization/oxidative aromatization cascade reaction of 2-hydroxy-1,4-diones

2019 ◽  
Vol 17 (32) ◽  
pp. 7547-7551 ◽  
Author(s):  
Qiang Sha ◽  
Haixuan Liu
Keyword(s):  
Trifluoroacetic Acid ◽  
De Novo ◽  
Cascade Reaction ◽  
De Novo Synthesis ◽  
Simple Metal ◽  
Metal Free ◽  
Aromatization Reaction ◽  
Oxidative Aromatization ◽  
Acid Catalyzed

A simple metal-free cyclization/oxidative aromatization reaction starting from 2-hydroxy-1,4-diones for the de novo synthesis of benzofurans was developed.

Stereoselective three-component cascade synthesis of α-substituted 2,4-dienamides from gem-difluorochloro ethanes

2019 ◽  
Vol 55 (95) ◽  
pp. 14355-14358
Author(s):  
Shyamsundar Das ◽  
Nakeun Ko ◽  
Eunsung Lee ◽  
Sang Eun Kim ◽  
Byung Chul Lee
Keyword(s):  
Transition Metal ◽  
Claisen Rearrangement ◽  
Cascade Reaction ◽  
One Pot ◽  
Metal Free

Herein, we describe a new transition metal-free Claisen rearrangement for the synthesis of α-substituted 2,4-dienamide. This one-pot, stereoselective three-component cascade reaction affords various polysubstituted 2,4-dienamides in good yields.

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