Insights on the Petasis Borono–Mannich multicomponent reaction mechanism

RSC Advances ◽  
2015 ◽  
Vol 5 (93) ◽  
pp. 76337-76341 ◽  
Author(s):  
Roberto Y. Souza ◽  
Giovana A. Bataglion ◽  
Davi A. C. Ferreira ◽  
Claudia C. Gatto ◽  
Marcos N. Eberlin ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Multicomponent Reaction ◽  
Mannich Reaction

The Petasis Borono–Mannich reaction: a joint theoretical and experimental.

Synthetic enzyme-catalyzed multicomponent reaction for Isoxazol-5(4H)-one Syntheses, their properties and biological application; why should one study mechanisms?

2021 ◽  
Author(s):  
Gabriela H. C. Oliveira ◽  
Luciana M. Ramos ◽  
Raíssa K. C. de Paiva ◽  
Saulo T. A. Passos ◽  
Marina M. Simões ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Multicomponent Reaction ◽  
Early Endosome ◽  
Biological Application ◽  
Multicomponent Synthesis

An imidazolium-containing synthetic enzyme (synzyme) is applied as the catalyst to promote the multicomponent synthesis of (fluorescent) isoxazol-5(4H)-one derivatives in water. The reaction mechanism and selective early endosome staining are also disclosed.

scholarly journals Efficient Straightforward Synthesis of Amidopiperazinophanes as Versatile Novel Supramolecular Scaffolds

SynOpen ◽  
2019 ◽  
Vol 03 (04) ◽  
pp. 157-163
Author(s):  
Ayyavu Thirunarayanan ◽  
Sivasamy Selvarani ◽  
Gracia Francisco ◽  
Perumal Rajakumar
Keyword(s):  
Electron Donor ◽  
Multicomponent Reaction ◽  
Mannich Reaction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Supramolecular Scaffolds ◽  
Donor Acceptor ◽  
The Mannich Reaction

A simple one-pot synthesis of amidopiperazinophanes with a combination of electron-deficient amide groups and electron-rich alkyne and piperazine functionalities has been achieved by using multicomponent reaction (MCR) methodology with the Mannich reaction. Herein, we demonstrate the synthesis of macrocyclic amide structures in good yields. These macrocycles, with electron donor/acceptor sites, are versatile molecules for host–guest and binding.

Convenient One-Pot Four-Component Synthesis of 6,8-Disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones via a Triple Mannich Reaction

2019 ◽  
Vol 72 (7) ◽  
pp. 542 ◽  
Author(s):  
Ahmed F. M. EL-Mahdy ◽  
Hassan A. H. El-Sherief ◽  
Zainab A. Hozien
Keyword(s):  
Reaction Mechanism ◽  
Functional Groups ◽  
Mannich Reaction ◽  
Spectroscopic Data ◽  
Atomic Charge ◽  
Secondary Amines ◽  
Primary Amines ◽  
One Pot ◽  
Elemental Analyses ◽  
Charge Calculations

An efficient and simple one-pot four-component protocol has been developed and performed for the synthesis of 6,8-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones, involving a triple Mannich reaction of 6-amino-2-(ethylthio)pyrimidin-4(3H)-one, formaldehyde, primary amines, and alcohols. Secondary amines were also utilised instead of alcohols as Mannich nucleophiles, and a variety of functional groups and electronically varied reaction partners were tolerated. This one-pot reaction facilitated the generation of a library of pyrimido[4,5-d]pyrimidin-4(3H)-ones in very good to excellent yields. The regioselectivity of this reaction was investigated using atomic charge calculations, and spectroscopic data confirmed that the triple Mannich products were 6,8-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones rather than the isomeric 3,6-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones. The structures of all compounds synthesised using the triple Mannich reaction were confirmed via spectroscopic and elemental analyses. The reaction mechanism was studied and confirmed by isolation of the intermediate.

Multicomponent reaction of conjugated enynones with malononitrile and sodium alkoxides: Complex reaction mechanism of the formation of pyridine derivatives

Tetrahedron ◽  
2019 ◽  
Vol 75 (33) ◽  
pp. 4516-4530
Author(s):  
Anastasiya V. Kuznetcova ◽  
Ivan S. Odin ◽  
Alexander A. Golovanov ◽  
Iakov M. Grigorev ◽  
Aleksander V. Vasilyev
Keyword(s):  
Reaction Mechanism ◽  
Multicomponent Reaction ◽  
Complex Reaction ◽  
Pyridine Derivatives

scholarly journals Diastereoselective Ugi reaction of chiral 1,3-aminoalcohols derived from an organocatalytic Mannich reaction

2016 ◽  
Vol 12 ◽  
pp. 139-143 ◽  
Author(s):  
Samantha Caputo ◽  
Andrea Basso ◽  
Lisa Moni ◽  
Renata Riva ◽  
Valeria Rocca ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Multicomponent Reaction ◽  
Mannich Reaction ◽  
Ugi Reaction ◽  
Enantiomerically Pure ◽  
Stereogenic Centers

Enantiomerically pure β-aminoalcohols, produced through an organocatalytic Mannich reaction, were subjected to an Ugi multicomponent reaction under classical or Lewis acid-promoted conditions with diastereoselectivities ranging from moderate to good. This approach represents a step-economical path to enantiomerically pure, polyfunctionalized peptidomimetics endowed with three stereogenic centers, allowing the introduction of five diversity inputs.

scholarly journals A Brønsted Acid-Catalyzed Multicomponent Reaction for the Synthesis of Highly Functionalized γ-Lactam Derivatives

Molecules ◽  
2019 ◽  
Vol 24 (16) ◽  
pp. 2951 ◽  
Author(s):  
Corte ◽  
Marigorta ◽  
Palacios ◽  
Vicario
Keyword(s):  
Phosphoric Acid ◽  
Multicomponent Reaction ◽  
Mannich Reaction ◽  
Acid Catalyst ◽  
Selective Hydrolysis ◽  
Reaction Conditions ◽  
Amide Derivatives ◽  
Acid Catalyzed ◽  
Hydrolysis Of

Brønsted acids catalyze a multicomponent reaction of benzaldehyde with amines and diethyl acetylenedicarboxylate to afford highly functionalized γ-lactam derivatives. The reaction consists of a Mannich reaction of an enamine to an imine, both generated in situ, promoted by a phosphoric acid catalyst and a subsequent intramolecular cyclization. The hydrolysis of the cyclic enamine substrate can provide enol derivatives and, moreover, a second attack of the amine on the carboxylate can afford amide derivatives. An optimization of the reaction conditions is presented in order to obtain selectively cyclic enamines that can afford the enol species after selective hydrolysis.

Arylation of enelactams using TIPSOTf: reaction scope and mechanistic insight

2021 ◽  
Author(s):  
Tomasz J. Idzik ◽  
Zofia M. Myk ◽  
Łukasz Struk ◽  
Magdalena Perużyńska ◽  
Gabriela Maciejewska ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Multinuclear Nmr ◽  
Mechanistic Insight ◽  
Nmr Study ◽  
Wide Range

Triisopropylsilyltrifluoromethanesulfonate can be effectively used for the arylation of a wide range of enelactams. The multinuclear NMR study provided deep insights into the reaction mechanism.

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