Facile Multicomponent Mannich Reaction towards Biologically Active Compounds

Borah, Preetismita; Borah, Gongutri; Nath, Arabinda Chandra; Latif, Wajid; Banik, Bimal K.

doi:10.1002/slct.202203758

Cited by 10 publications

(6 citation statements)

References 122 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The introduction of the positively charged amine groups in the lignin structure fulfils these goals [21] . The Mannich reaction is a fundamental organic chemical reaction used for the synthesis of amino ketones or esters, which are used to prepare the synthetic building blocks in the preparation of biological nitrogen‐contained compounds [22] . Further, the execution of the reaction is a facile approach, occurring (Figure 2) between the lignin, amines, and formaldehyde under acidic, neutral, and alkaline conditions [9,17] …”

Section: Mannich Modified Lignin and Their Applicationsmentioning

confidence: 99%

Mannich Reaction: Review of Amine‐Functionalized Lignin Derivatives and Their Applications

et al. 2023

View full text Add to dashboard Cite

In recent years naturally resourced materials have played a significant role in many applications ranging from biomedical to automotive applications. Among them, lignin has received much attention towards these applications owing to its abundance and readily modified chemical structures. Recent research studies have focused on various chemical modifications of lignin, including the increasingly popular Mannich reaction that aminates the lignin structure to expand the applicability of lignin in advanced fields. This article reviews the recent Mannich reaction‐based lignin developments with different types of amines used in lignin modifications and discusses how the reaction enhances functionality in engineering, biomedical and environmental technology applications.

show abstract

Section: Mannich Modified Lignin and Their Applicationsmentioning

confidence: 99%

Mannich Reaction: Review of Amine‐Functionalized Lignin Derivatives and Their Applications

et al. 2023

View full text Add to dashboard Cite

show abstract

“…Multicomponent reactions (MCRs) are highly convergent processes that can be used to create new potent bioactive molecules. On the basis of green chemistry [ 1 ], MCRs benefit from efficiency, energy, time and atom economies, use environmentally favorable conditions and decrease the amount of byproducts and/or waste [ 2 , 3 , 4 , 5 , 6 , 7 , 8 ]. In addition, MCRs provide one of the most attractive prospects concerning complexity and diversity for the preparation of chemical libraries compared with other traditional synthetic organic methods.…”

Section: Introductionmentioning

confidence: 99%

Diastereoselective ZnCl2-Mediated Joullié–Ugi Three-Component Reaction for the Preparation of Phosphorylated N-Acylaziridines from 2H-Azirines

Allende,

Olaizola,

Ochoa de Retana

et al. 2024

Molecules

View full text Add to dashboard Cite

We disclose a direct approach to the diastereoselective synthesis of phosphorus substituted N-acylaziridines based on a one-pot ZnCl2-catalyzed Joullié–Ugi three-component reaction of phosphorylated 2H-azirines, carboxylic acids and isocyanides. Hence, this robust protocol offers rapid access to an array of N-acylaziridines in moderate-to-good yields and up to 98:2 dr for substrates over a wide scope. The relevance of this synthetic methodology was achieved via a gram-scale reaction and the further derivatization of the nitrogen-containing three-membered heterocycle. The diastereo- and regioselective ring expansion of the obtained N-acylaziridines to oxazole derivatives was accomplished in the presence of BF3·OEt2 as an efficient Lewid acid catalyst.

show abstract

“…To be specific, only two isolated examples of NH- [18] or SO 2 -substituted [19] bicyclic compounds were reported in the literature (Scheme 1, A). In both works, the synthetic approach commenced from the corresponding cyclic ketones and included the double Mannich reaction, [20][21][22] subsequent deoxofluorination, [23,24] and cleavage of the protective groups. In both cases, no illustration of the potential for synthetic modifications and isosteric replacements was made for the discussed scaffolds.…”

Section: Introductionmentioning

confidence: 99%

gem‐Difluoro‐3‐azabicyclo[3.n.1]alkanes and Their Derivatives – Bicyclic Fluorinated Piperidine Isosteres for Drug Discovery

Kihakh,

Melnykov,

Bilenko

et al. 2023

Eur J Org Chem

View full text Add to dashboard Cite

An approach to gem‐difluoro‐3‐azabicyclo[3.n.1]alkane‐ derived building blocks via double‐Mannich addition – deoxofluorination sequence is described. The scope of the method was demonstrated for a series of saturated (hetero)cyclic ketones or ketoesters (including five‐ to seven‐membered cycloalkane derivatives and N‐, O‐, S‐containing saturated heterocycles). Further transformations of functional groups produced a number of bifunctionalized difluorinated building blocks, namely, N‐protected aminoacids, mono‐N‐Boc‐protected diamines, and unprotected aminoalcohols in good to excellent overall yields. For the azabicyclo[3.3.1]alkane series, a potential for isosteric replacements is demonstrated by evaluation of the key physicochemical properties (i.e., pKa(H) and LogP).

show abstract

Facile Multicomponent Mannich Reaction towards Biologically Active Compounds

Cited by 10 publications

References 122 publications

Mannich Reaction: Review of Amine‐Functionalized Lignin Derivatives and Their Applications

Mannich Reaction: Review of Amine‐Functionalized Lignin Derivatives and Their Applications

Diastereoselective ZnCl2-Mediated Joullié–Ugi Three-Component Reaction for the Preparation of Phosphorylated N-Acylaziridines from 2H-Azirines

gem‐Difluoro‐3‐azabicyclo[3.n.1]alkanes and Their Derivatives – Bicyclic Fluorinated Piperidine Isosteres for Drug Discovery

Contact Info

Product

Resources

About