Synthesis of 3-Oxoisoindoline-1-carboxamides through Sequential Four-Component Ugi Reaction/Oxidative Nucleophilic Substitution of Hydrogen

This paper describes a diversity-oriented approach to the formation of 3-oxoisoindoline-1-carboxamide derivatives utilizing the potential of the nitro group as a directing group. The reaction proceeds through a novel class of post-transformation reactions through a sequential four-component Ugi reaction/oxidative nucleophilic substitution of hydrogen. The 3-oxoisoindoline-1-carboxamide derivatives were synthesized in the presence of a base under mild reaction conditions with high regio- and chemoselectivity. The aerobic oxidation, high bond-forming efficiency, high atom economy, and good to excellent yields are the main advantages of this approach.

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A Domino Approach for the Synthesis of 4-Carboxamide Oxazolines from Azirines

Synthesis ◽

10.1055/a-1558-7457 ◽

2021 ◽

Author(s):

Ali Nikbakht ◽

Fariba Mohammadi ◽

Mohammad Sadeq Mousavi ◽

Kamran Amiri ◽

Saeed Balalaie ◽

...

Keyword(s):

Carboxylic Acids ◽

Ring Expansion ◽

Target Product ◽

Atom Economy ◽

Reaction Conditions ◽

Bond Forming ◽

Forming Efficiency ◽

High Bond ◽

Ring Expansion Reaction ◽

Indium Catalyst

A regio- and the diastereoselective ring-expansion reaction of N-acyl aziridine has been described for the synthesis of 4-carboxamide oxazolines using InCl3. A domino Ugi-Joullié/ring expansion reaction of arylphenylazirines, isocyanides, and carboxylic acids led to the target product through N-acylaziridine intermediate in the presence of indium catalyst. The oxazolines were synthesized in moderate to excellent yields with high atom-economy and high bond-forming efficiency under mild reaction conditions.

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Catalyst-Free Synthesis of Fused Triazolo-Diazepino[5,6-b]Quinoline Derivatives via a Sequential Ugi-4CR–Nucleophilic Substitution–Intramolecular Click Reaction

Synlett ◽

10.1055/s-0036-1591531 ◽

2018 ◽

Vol 29 (08) ◽

pp. 1095-1101 ◽

Cited By ~ 8

Author(s):

Saeed Balalaie ◽

Aref Vaezghaemi ◽

Nahid Zarezadeh ◽

Frank Rominger ◽

Hamid Bijanzadeh

Keyword(s):

Nucleophilic Substitution ◽

Click Reaction ◽

Quinoline Derivatives ◽

Wide Scope ◽

Bond Forming ◽

Catalyst Free ◽

Forming Efficiency ◽

High Bond

A convenient, post-transformational reaction has been developed for the construction of highly diversified quinoline-fused triazolo-diazepinones featuring four diversification points by employing a catalyst-free Ugi four-component–nucleophilic substitution–intramolecular click cycloaddition sequence. This approach provides a wide scope of products with good yields and high bond-forming efficiency.

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The Eschenmoser coupling reaction under continuous-flow conditions

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.7.135 ◽

2011 ◽

Vol 7 ◽

pp. 1164-1172 ◽

Cited By ~ 13

Author(s):

Sukhdeep Singh ◽

J Michael Köhler ◽

Andreas Schober ◽

G Alexander Groß

Keyword(s):

Continuous Flow ◽

Elevated Temperatures ◽

Reaction Times ◽

Coupling Reaction ◽

Flow Chemistry ◽

Flow Conditions ◽

Reaction Conditions ◽

Bond Forming ◽

Carbon Carbon Bond ◽

Reaction Proceeds

The Eschenmoser coupling is a useful carbon–carbon bond forming reaction which has been used in various different synthesis strategies. The reaction proceeds smoothly if S-alkylated ternary thioamides or thiolactames are used. In the case of S-alkylated secondary thioamides or thiolactames, the Eschenmoser coupling needs prolonged reaction times and elevated temperatures to deliver valuable yields. We have used a flow chemistry system to promote the Eschenmoser coupling under enhanced reaction conditions in order to convert the demanding precursors such as S-alkylated secondary thioamides and thiolactames in an efficient way. Under pressurized reaction conditions at about 220 °C, the desired Eschenmoser coupling products were obtained within 70 s residence time. The reaction kinetics was investigated and 15 examples of different building block combinations are given.

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A one-pot synthesis of [1,2,3]triazolo[1,5-a]quinoxalines from 1-azido-2-isocyanoarenes with high bond-forming efficiency

Chemical Communications ◽

10.1039/c6cc08543a ◽

2017 ◽

Vol 53 (7) ◽

pp. 1305-1308 ◽

Cited By ~ 22

Author(s):

Dengke Li ◽

Tingting Mao ◽

Jinbo Huang ◽

Qiang Zhu

Keyword(s):

One Pot ◽

Efficient Approach ◽

Bond Forming ◽

One Pot Synthesis ◽

Forming Efficiency ◽

High Bond ◽

Terminal Acetylenes

An efficient approach to prepare 1,2,3-triazolo[1,5-a]quinoxaline scaffolds, starting from 1-azido-2-isocyanoarenes and terminal acetylenes or substituted acetaldehydes, has been developed.

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Intermolecular C–H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis

Synthesis ◽

10.1055/a-1401-4486 ◽

2021 ◽

Author(s):

Zheng-Yang Gu ◽

Yang Wu ◽

Feng Jin ◽

Bao Xiaoguang ◽

Ji-Bao Xia

Keyword(s):

Carbon Monoxide ◽

Palladium Catalysis ◽

Computational Studies ◽

Organic Azides ◽

Reaction Proceeds ◽

Palladium Catalyzed ◽

Directing Group ◽

And Control

An atom- and step-economic intermolecular multi-component palladium-catalyzed C–H amidation of alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho-directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.

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