The Ugi Multicomponent Reaction for the One‐Step Construction of Macrocycles DOI Open Access
Yi‐Ming Chen, Xue Li, Zhigang Xu

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: March 21, 2025

The exploration of macrocycles began in the 20th century, coinciding with progressive advancement synthetic chemistry methodologies. From numerous strategies, Ugi reaction stands out as an efficacious four-component (4-CR). is particularly distinguished by its robust functional group tolerance, enabling creation that are both diverse and complex a singular step. This review collates contemporary examples macrocycles, all which have been crafted using to construct these macrocyclic frameworks. employment various bifunctional reagents (with same or different groups), has introduced plethora cyclization tactics, resulting synthesis multitude cage molecules. In order offer invaluable insights into construction use distinct colors for reactants made entire process transparently visible, thereby enhancing readers' understanding sparking their interest.

Language: Английский

Stereocontrolled synthesis of an α–monosubstituted α–amino acid derivative from a Ugi reaction product DOI
Shuntaro Tsukamoto,

Yuki Suzuki,

Masato Oikawa

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155488 - 155488

Published: Jan. 1, 2025

Language: Английский

Citations

0

Antibacterial properties of nanocomposites based on titanate nanotubes and bacterial nanocellulose functionalized through UGI reaction DOI
Agostinho Cruz, Gustavo Henrique Couto, Cristiane Pilissão

et al.

Cellulose, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 20, 2025

Language: Английский

Citations

0

New tandem Ugi/intramolecular Diels–Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives DOI Creative Commons
Yuriy I. Horak, Roman Z. Lytvyn,

A.R. Vakhula

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 444 - 450

Published: Feb. 26, 2025

A new tandem sequence involving the Ugi reaction and Diels-Alder [4 + 2] cycloaddition based on vinylfuran 1,3-butadienylfuran derivatives was designed studied. It found that in case of 3-(furan-2-yl)acrylaldehyde, a one-pot intramolecular vinylarene (IMDAV) leads to formation insufficiently studied furo[2,3-f]isoindole derivatives. adducts formed from (E)-3-(furan-2-yl)acrylaldehyde, maleic acid monoanilide, isonitrile, an amine spontaneously underwent IMDAV with high level stereoselectivity, leading single pairs enantiomers 4,4a,5,6,7,7a-hexahydro-3aH-furo[2,3-f]isoindole core excellent yields. Under same conditions, (2E,4E)-5-(furan-2-yl)penta-2,4-dienal gives adduct undergoes IMDA without furan core. The 2,3,3a,4,5,7a-hexahydro-1H-isoindoles reactions allow substituent variation named isoindoles.

Language: Английский

Citations

0

Unlocking Enol-Ugi-Derived Conformationally Restricted Peptidomimetic Motifs DOI
José Luis Ramiro, Jesús Dı́az, Ana G. Neo

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 13, 2025

The enol-Ugi condensation, a versatile multicomponent reaction, provides rapid and efficient route to enamine peptidomimetics. In this study, we investigated the factors influencing conformational behavior of three adducts with distinct structural features. Through DFT calculations NCI analysis, identified that noncovalent interactions, including hydrogen bonds π–π play pivotal role in restricting flexibility. While six-membered cyclic enamines 6 7 exhibited varying degrees rotational freedom, indanone-derived 8 displayed locked conformation resembling retropeptidic turn. These findings highlight potential tailoring mimic biologically relevant peptidic motifs, opening new avenues for drug discovery design.

Language: Английский

Citations

0

The Ugi Multicomponent Reaction for the One‐Step Construction of Macrocycles DOI Open Access
Yi‐Ming Chen, Xue Li, Zhigang Xu

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: March 21, 2025

The exploration of macrocycles began in the 20th century, coinciding with progressive advancement synthetic chemistry methodologies. From numerous strategies, Ugi reaction stands out as an efficacious four-component (4-CR). is particularly distinguished by its robust functional group tolerance, enabling creation that are both diverse and complex a singular step. This review collates contemporary examples macrocycles, all which have been crafted using to construct these macrocyclic frameworks. employment various bifunctional reagents (with same or different groups), has introduced plethora cyclization tactics, resulting synthesis multitude cage molecules. In order offer invaluable insights into construction use distinct colors for reactants made entire process transparently visible, thereby enhancing readers' understanding sparking their interest.

Language: Английский

Citations

0