Synthesis of Oxazolidin‐2‐ones <i>via</i> a Copper(I)‐Catalyzed Tandem Decarboxylative/Carboxylative Cyclization of a Propiolic Acid, a Primary Amine and an Aldehyde

Feng, Huangdi; Ermolat’ev, Denis S.; Song, Gonghua; Eycken, Erik V. Van der

doi:10.1002/adsc.201100608

Cited by 54 publications

(19 citation statements)

References 54 publications

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“…In the same year, Ermolat′ev, Van der Eycken and co‐workers reported a copper‐catalyzed multicomponent reaction that used 3‐substituted propiolic acids as the source of both the alkynes and CO 2 (Scheme ), thereby providing an efficient approach for the synthesis of oxazolidin‐2‐ones under mild reaction conditions . Importantly, diverse aldehydes, primary amines, and propiolic acids, including both 3‐aryl and 3‐alkyl propiolic acids, were suitable in this process.…”

Section: Cyclization Reactions Of Propargylic Amines With Co2mentioning

confidence: 99%

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO₂ by Using Homogeneous Catalysis

Zhang

et al. 2018

Chemistry An Asian Journal

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Carbon dioxide (CO ), a well-known greenhouse gas, is also a nontoxic, readily accessible, and renewable one-carbon (C1) source. However, owing to its thermodynamic stability and kinetic inertness, the efficient utilization of CO is challenging. Much effort has been devoted to achieving efficient and selective organic transformations of CO . Recently, the synthesis of important oxazolidin-2-ones from unsaturated amines by using CO has attracted much attention and been heavily studied. This Focus Review presents recent advances in this area by using homogenous catalysis. The cyclization of amines that contain alkynes, alkenes, and allenes with CO is discussed, and possible reaction mechanisms and applications of these transformations are also described.

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Section: Cyclization Reactions Of Propargylic Amines With Co2mentioning

confidence: 99%

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO₂ by Using Homogeneous Catalysis

Zhang

et al. 2018

Chemistry An Asian Journal

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“…In addition, substituted 2‐aminopyridines also produced the desired imidazo[1,2‐ a ]pyridines 4aa‐1 and 4aa‐2 in moderate to good yields. In no case did we find the decarboxylative/carboxylative cyclized products recently reported by Van der Eycken 19…”

Section: Resultsmentioning

confidence: 60%

Copper‐Catalyzed Decarboxylative Three‐Component Reactions for the Synthesis of Imidazo[1,2‐a]pyridines

Palani¹,

Park²,

Kumar³

et al. 2012

Eur J Org Chem

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Imidazo[1,2‐a]pyridine derivatives were synthesized through multicomponent coupling reactions of 2‐aminopyridines, aldehydes, and alkynecarboxylic acids in the presence of 10 mol‐% CuI/Cu(OTf)2. Both aryl‐ and alkyl‐substituted alkynecarboxylic acids, including propiolic acid, were good alkyne sources and afforded the desired imidazo[1,2‐a]pyridines in good yields through the decarboxylative coupling reactions. Arylalkynecarboxylic acids were synthesized through palladium‐catalyzed coupling reactions between aryl iodides and propiolic acid and reacted with 2‐aminopyridine and aldehydes, with or without a purification step. In both cases the desired imidazo[1,2‐a]pyridines were obtained in good yields. Mechanistic studies suggested that in the case of propiolic acid the decarboxylative addition predominates over terminal alkyne addition.

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“…When a primary amine such as cyclohexylamine was employed, the desired propargyl amine 4 s was formed in 25 % yield along with cyclized product oxazolidin‐2‐one 5 in 10 % yield (Scheme ). The formation of the oxazolidin‐2‐one from the decarboxylative coupling of an alkynyl carboxylic acid with a primary amine was reported by Van der Eycken . They also reported that a propargyl amine was formed in low yield from the reaction of a terminal alkyne, glyoxylic acid, and a primary amine .…”

Section: Resultsmentioning

confidence: 85%

Copper‐Catalyzed Double Decarboxylative Coupling Reactions of Alkynyl Carboxylic Acid and Glyoxylic Acid: Synthesis of Propargyl Amines and Imidazopyridines

et al. 2016

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The reactiono fa lkynyl carboxylic acids, glyoxylic acid derivatives, and amines in the presence of ac opper catalyst afforded the corresponding propargyl amines in good yields. The alkynyl carboxylic acid of this coupling reaction shows similarr eactivity to that of at erminal alkyne, and the reactivityo ft he glyoxylic acid is almost identicalt ot hat of an aldehyde. When 2-aminopyridine was employed as the amine source, imidazopyridine derivatives weref ormedi n good yields.Scheme1.Different approaches to the synthesis of propargyl amines.[a] J.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under http://dx.

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Synthesis of Oxazolidin‐2‐ones via a Copper(I)‐Catalyzed Tandem Decarboxylative/Carboxylative Cyclization of a Propiolic Acid, a Primary Amine and an Aldehyde

Cited by 54 publications

References 54 publications

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO₂ by Using Homogeneous Catalysis

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO₂ by Using Homogeneous Catalysis

Copper‐Catalyzed Decarboxylative Three‐Component Reactions for the Synthesis of Imidazo[1,2‐a]pyridines

Copper‐Catalyzed Double Decarboxylative Coupling Reactions of Alkynyl Carboxylic Acid and Glyoxylic Acid: Synthesis of Propargyl Amines and Imidazopyridines

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Synthesis of Oxazolidin‐2‐ones via a Copper(I)‐Catalyzed Tandem Decarboxylative/Carboxylative Cyclization of a Propiolic Acid, a Primary Amine and an Aldehyde

Cited by 54 publications

References 54 publications

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO2 by Using Homogeneous Catalysis

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO2 by Using Homogeneous Catalysis

Copper‐Catalyzed Decarboxylative Three‐Component Reactions for the Synthesis of Imidazo[1,2‐a]pyridines

Copper‐Catalyzed Double Decarboxylative Coupling Reactions of Alkynyl Carboxylic Acid and Glyoxylic Acid: Synthesis of Propargyl Amines and Imidazopyridines

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Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO₂ by Using Homogeneous Catalysis

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO₂ by Using Homogeneous Catalysis