Essential Multicomponent Reactions II

Könning, Daniel; Swatschek, Jörg

doi:10.1002/9781118863992.ch13

Cited by 2 publications

(1 citation statement)

References 351 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…By means of multicomponent domino reactions (MCDRs), multiple bonds can be formed consecutively in one pot from several building blocks or from an in situ-formed intermediate with a strategically positioned reactive site. − It is well-known that functionalized 1,4-dihydropyridines can readily be prepared in one pot via a four-component reaction of Hantzsch reagents (aldehydes, amines, and two 1,3-dicarbonyl molecules). − Technically, however, treatment of Hantzsch reagents could also result in another structure, 2-amino-3,4-dihydropyran, via nucleophilic attack of enolate to the electron-deficient imine in the final step of cyclization. Considering the above points and our continued interest in the one-pot synthesis of heterocyclic compounds − wherein iodine is used as a Lewis acid catalyst, we designed a five-component Hantzsch-type reaction (Figure ) to construct a novel molecule bearing a 2-amino-3,4-dihydropyran-3-carboxamide core.…”

Section: Introductionmentioning

confidence: 99%

Diastereoselective Synthesis of 3,4-Dihydropyran-3-carboxamides with in Vitro Anti-inflammatory Activity

Zeng

Huang

et al. 2019

ACS Comb. Sci.

View full text Add to dashboard Cite

A versatile and economical reaction of diketene (1), aryl amines 2, cyclic 1,3-diketones 3, primary amines 4, and aryl aldehydes 5 was explored to synthesize 3,4-dihydropyran-3-carboxamide derivatives under mild conditions. Three stereogenic centers are generated in the products, and the structure of the major diastereomer of 6{1,1,3,1} was identified by X-ray diffraction and 2D NMR spectroscopy. The scope and limitation investigation provided two series of (2S,3R,4S)-chromene-3-carboxamides in good to excellent yields with high diastereoselectivity. Two products, 6{5,3,1,1} and 6{7,3,1,1}, exhibited in vitro anti-inflammatory activity with significant inhibition of pro-inflammatory cytokine IL-6 and TNF-α expression in lipopolysaccharide (LPS)-treated Raw 264.7 cells.

show abstract

Section: Introductionmentioning

confidence: 99%

Diastereoselective Synthesis of 3,4-Dihydropyran-3-carboxamides with in Vitro Anti-inflammatory Activity

Zeng

Huang

et al. 2019

ACS Comb. Sci.

View full text Add to dashboard Cite

show abstract

Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

Campos-Prieto,

García-Rey,

Sotelo

et al. 2024

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

The ongoing quest to discover effective treatments for diseases remains a significant challenge for the scientific community. Multicomponent reactions (MCRs) have emerged as powerful tools in accelerating drug discovery, enabling the rapid generation of chemical libraries with high diversity in a time-efficient and environmentally sustainable manner. In this review, we focus on central nervous system (CNS) disorders, particularly Alzheimer's disease, Parkinson's disease, schizophrenia, depression, and epilepsy, where MCRs have contributed to the development of promising ligands in recent years. Rather than providing an exhaustive overview, this review aims to highlight key studies that address major CNS pathologies, relevant drug targets, and various MCR approaches. We have carefully selected representative articles and apologize to the authors whose important contributions may not be included. By concentrating on these pivotal studies, we strive to offer a clear and concise perspective on current research trends and breakthroughs in this field.

show abstract

Essential Multicomponent Reactions II

Cited by 2 publications

References 351 publications

Diastereoselective Synthesis of 3,4-Dihydropyran-3-carboxamides with in Vitro Anti-inflammatory Activity

Diastereoselective Synthesis of 3,4-Dihydropyran-3-carboxamides with in Vitro Anti-inflammatory Activity

Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

Contact Info

Product

Resources

About