Organocatalytic multicomponent coupling to access a highly functionalised tetracyclic furoindoline: interrupted Passerini/Joullié–Ugi cascade reaction

Yamada, Takeshi; Okamoto, Sentaro

doi:10.1039/d2cc04429c

Cited by 3 publications

(1 citation statement)

References 20 publications

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“…In particular, 2-pyridone is capable of catalyzing isomerization reactions occurring at the anomeric positions of sugars (Scheme 2a) [2] , various nucleophilic aromatic substitution reactions (Scheme 2b), [3,4] Passellini-type reactions (Scheme 2c) [5,6] and ester-amide exchange reactions (Scheme 2d). Our research has focused on the latter reactions because these offer the most versatility.…”

Section: Introductionmentioning

confidence: 99%

Ester-Amide Exchange Reactions Using 2-Pyridone derivatives as Tautomeric Catalysts

Mihara,

Yotsuji,

Imayoshi

et al. 2024

Preprint

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The application of 2-pyridone as a tautomeric catalyst for ester-amide exchange reactions was investigated. This compound was found to be most effective at accelerating these reactions when 4-nitrophenyl acetate was used as an acylating agent in toluene. Primary amines without branching at the α-position were determined to be the most suitable substrates. Various 2-pyridone derivatives having an electron-donating group at the 5-position (including methoxy and pirrolidino groups) exhibited superior performance. Acylation reactions of mixtures of primary and secondary amines preferentially acylated the latter compounds in the absence of a catalyst or with N,N-dimethylaminopyridine (DMAP) as the catalyst, whereas primary amines were acylated in the case that a 2-pyridone derivative with a pirrolidino group was employed. The reaction mechanism associated with this preferential acylation process was evaluated and is discussed herein.

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Section: Introductionmentioning

confidence: 99%

Ester-Amide Exchange Reactions Using 2-Pyridone derivatives as Tautomeric Catalysts

Mihara,

Yotsuji,

Imayoshi

et al. 2024

Preprint

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Facile synthesis of dihydroisobenzofuran derivatives via a one-pot sequential Passerini-azide/Ag(I)-catalyzed cyclization process

Luo,

Yu,

Yang

et al. 2024

Tetrahedron

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Domino Michael/Oxa-Michael Reactions of the Unsymmetric Double Michael Acceptor for Access to Bicyclic Furo[2,3-b]pyrrole

Li,

Wang,

Zhou

et al. 2024

J. Org. Chem.

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By creating an unsymmetric double Michael acceptor 1, we were able to synthesize the nonaromatic-fused bicyclic furo[2,3-b]pyrrole nucleus using a domino Michael/oxa-Michael reaction. Adopting benzoyl acetonitrile 2d (CN as the electronwithdrawing group) as a substrate, we discovered a (DHQ) 2 AQN-catalyzed method for high diastereo-and enantioselectivity of those products. The reaction path has been determined by isolating the reaction intermediates, and density functional theory calculations support these findings. Beyond providing a synthetic approach, this work illustrated the compounds' possible use in antitumor activity.

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Organocatalytic multicomponent coupling to access a highly functionalised tetracyclic furoindoline: interrupted Passerini/Joullié–Ugi cascade reaction

Abstract: The interrupted Passerini reaction of 3-(2-isocyanoethyl)-indole catalysed by 3,5,6-trifluoro-2-pyridone is described. The reaction diastereoselectively provided a tetracyclic furolindoline, which proved to be a good substrate for the Joullié–Ugi reaction; therefore,...

Cited by 3 publications

References 20 publications

Ester-Amide Exchange Reactions Using 2-Pyridone derivatives as Tautomeric Catalysts

Ester-Amide Exchange Reactions Using 2-Pyridone derivatives as Tautomeric Catalysts

Facile synthesis of dihydroisobenzofuran derivatives via a one-pot sequential Passerini-azide/Ag(I)-catalyzed cyclization process

Domino Michael/Oxa-Michael Reactions of the Unsymmetric Double Michael Acceptor for Access to Bicyclic Furo[2,3-b]pyrrole

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