Pd-Catalyzed Dearomative Three-Component Reaction of Bromoarenes with Diazo Compounds and Allylborates

2019 ◽  
Author(s):  
Masaaki Komatsuda ◽  
Hiroki Kato ◽  
Kei Muto ◽  
Junichiro Yamaguchi
Keyword(s):  
Diazo Compound ◽  
Diazo Compounds ◽  
Reaction Conditions ◽  
Three Component Reaction

Acatalytic dearomative three-component reaction of bromoarenes with TMS-diazomethane and allyl borate was developed. The key of this assembling reaction is the use of a diazo compound to generate a Pd-π-benzyl intermediate through a Pd-carbenoid species. This method allowed for a dearomative functionalization using arenes as limiting reagents. Heteroaryl bromides were also applicable to give dearomatized structures under the reaction conditions.

scholarly journals Pd-Catalyzed Dearomative Three-Component Reaction of Bromoarenes with Diazo Compounds and Allylborates

2019 ◽  
Author(s):  
Masaaki Komatsuda ◽  
Hiroki Kato ◽  
Kei Muto ◽  
Junichiro Yamaguchi
Keyword(s):  
Diazo Compound ◽  
Diazo Compounds ◽  
Reaction Conditions ◽  
Three Component Reaction

Acatalytic dearomative three-component reaction of bromoarenes with TMS-diazomethane and allyl borate was developed. The key of this assembling reaction is the use of a diazo compound to generate a Pd-π-benzyl intermediate through a Pd-carbenoid species. This method allowed for a dearomative functionalization using arenes as limiting reagents. Heteroaryl bromides were also applicable to give dearomatized structures under the reaction conditions.

Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja
Keyword(s):  
Efficient Method ◽  
Atom Economy ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.

Synthesis of pyrazolo[1,5-c]quinazoline derivatives through the copper-catalyzed domino reaction of o-alkenyl aromatic isocyanides with diazo compounds

2020 ◽  
Vol 56 (55) ◽  
pp. 7665-7668 ◽  
Author(s):  
Lu Liu ◽  
Lei Li ◽  
Shukuan Mao ◽  
Xin Wang ◽  
Ming-Dong Zhou ◽  
...  
Keyword(s):  
Diazo Compounds ◽  
Domino Reaction ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Quinazoline Derivatives

Various o-alkenyl aromatic isocyanides were prepared from readily available reactants for their double annulation with diazo compounds for a one-pot synthesis of pyrazolo[1,5-c]quinazolines under mild reaction conditions.

Palladium‐Catalyzed Three‐Component Reaction of Allenes, Aryl Iodides, and Diazo Compounds: Approach to 1,3‐Dienes

2013 ◽  
Vol 125 (35) ◽  
pp. 9475-9478 ◽  
Author(s):  
Qing Xiao ◽  
Binglong Wang ◽  
Leiming Tian ◽  
Yang Yang ◽  
Jian Ma ◽  
...  
Keyword(s):  
Diazo Compounds ◽  
Aryl Iodides ◽  
Three Component Reaction ◽  
Palladium Catalyzed

scholarly journals A Simple and Efficient Synthesis of Highly Substituted Indeno[1,2-b]pyrrole and Acenaphtho[1,2-b]pyrrole Derivatives by Tandem Three-Component Reactions

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 3031 ◽  
Author(s):  
Xiaodong Tang ◽  
Songlei Zhu ◽  
Ying Ma ◽  
Ren Wen ◽  
Lanqi Cen ◽  
...  
Keyword(s):  
Environmentally Benign ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Dicarbonyl Compounds ◽  
Pyrrole Derivatives ◽  
Three Component Reaction ◽  
High Yields ◽  
Operational Simplicity

A green, convenient and tandem procedure for the efficient synthesis of highly substituted indeno[1,2-b]pyrrole and acenaphtho[1,2-b]pyrrole derivatives by domino three-component reaction of tryptamine/benzylamine, 1,3-dicarbonyl compounds and ninhydrin/ acenaphthenequinone is described. The significant features of this procedure were characterized by mild reaction conditions, high yields, operational simplicity and it being environmentally benign.

scholarly journals A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

2019 ◽  
Vol 15 ◽  
pp. 1523-1533 ◽  
Author(s):  
András György Németh ◽  
György Miklós Keserű ◽  
Péter Ábrányi-Balogh
Keyword(s):  
Elemental Sulfur ◽  
Building Blocks ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
Synthetic Procedure ◽  
Three Component Reaction ◽  
Wide Range ◽  
Organic Chemist ◽  
The One

A new multicomponent reaction has been developed between isocyanides, sulfur and alcohols or thiols under mild reaction conditions to afford O-thiocarbamates and dithiocarbamates in moderate to good yields. The one-pot reaction cascade involves the formation of an isothiocyanate intermediate, thus a catalyst-free synthesis of isothiocyanates, as valuable building blocks from isocyanides and sulfur is proposed, as well. The synthetic procedure suits the demand of a modern organic chemist, as it tolerates a wide range of functional groups, it is atom economic and easily scalable.

A Copper(I)-Mediated Tandem Three-Component Synthesis of 5-Allyl-1,2,3-triazoles

Synthesis ◽  
2019 ◽  
Vol 52 (05) ◽  
pp. 744-754
Author(s):  
Yoona Song ◽  
Soyun Lee ◽  
Palash Dutta ◽  
Jae-Sang Ryu
Keyword(s):  
Room Temperature ◽  
Reaction Conditions ◽  
One Pot ◽  
Three Component Reaction ◽  
High Yields

A copper(I)-mediated tandem three-component reaction using alkynes, azides, allyl iodides, CuI and NaNH2 is developed. The reactions proceed smoothly at room temperature to afford 5-allyl-1,2,3-triazoles, which can be further converted into 1,2,3-triazole-fused tricyclic scaffolds. This method features an efficient one-pot cascade route using commercial alkynes and affords the corresponding 5-allyl-1,2,3-triazoles with high yields and good selectivity under mild reaction conditions.

scholarly journals Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

2019 ◽  
Vol 15 ◽  
pp. 874-880
Author(s):  
Razieh Navari ◽  
Saeed Balalaie ◽  
Saber Mehrparvar ◽  
Fatemeh Darvish ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Room Temperature ◽  
High Selectivity ◽  
Domino Reaction ◽  
Primary Amines ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Efficient Approach ◽  
Three Component Reaction ◽  
High Yields

An efficient approach for the synthesis of pyrazolopyridines containing the aminochromane motif through a base-catalyzed cyclization reaction is reported. The synthesis was carried out through a three-component reaction of (arylhydrazono)methyl-4H-chromen-4-one, malononitrile, primary amines in the presence of Et3N at room temperature. However, carrying out the reaction under the same conditions without base led to a fused chromanyl-cyanopyridine. High selectivity, high atom economy, and good to high yields in addition to mild reaction conditions are the advantages of this approach.

scholarly journals Microwave Assisted Three Component Reaction Conditions to Obtain New Thiazolidinones with Different Heterocyclic Skeletons

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 38
Author(s):  
Fernando J. Lorenzo ◽  
Romina A. Ocampo ◽  
Sandra D. Mandolesi
Keyword(s):  
Microwave Irradiation ◽  
Thioglycolic Acid ◽  
Aldehyde Group ◽  
Green Solvent ◽  
Reaction Products ◽  
Reaction Conditions ◽  
One Pot ◽  
Microwave Assisted ◽  
Three Component Reaction ◽  
The One

We present here a new proposal for the “one pot” generation of new 4-thiazolidinones (9a–e) through a multicomponent reaction under microwave irradiation conditions, using aromatic and heteroaromatic amines (8a–e), absolute ethanol as a “green” solvent and modifying the aldehyde group in the glycosidic residue, synthesized from D-mannitol. The study is focused in the variation of the irradiation times and the concentration of thioglycolic acid in order to study the possibility of controlling the structure and/or stereochemistry of the products formed in the reaction. Thiazolidinones 9a–d were obtained with a 69–82% The generation of the corresponding reaction products were monitored by TLC and CG-MS, taking reaction aliquots. The conditions reaction proved to be chemoselective depending on the excess of acid and irradiation times.

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