Multi-Auto-Tandem Reaction to Access Site-Specific Functionalized Tricyclic Furo[3,2-c]coumarins and Naphtho[2,3-b]furan-4,9-diones DOI
Xiang Liu, Hexiang Wang, Dongxin Lin

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 24, 2025

A three-component multi-auto-tandem reaction for the construction of site-specific tricyclic furo[3,2-c]coumarins via formation C-C, C-O, and C-S bonds in one step from 4-hydroxycoumarins/4-hydroxy-2-pyrones, ynals, sodium sulfinates is reported. This cascade efficiently produces a variety rare C-2-functionalized moderate to good yields under straightforward conditions. Furthermore, this protocol can be extended coupling involving 2-hydroxy-1,4-naphthoquinone, sulfinates, yielding naphtho[2,3-b]furan-4,9-dione derivatives. Notably, carbonyl group α-position ynals act as C-2 synthons specific reaction, enabling two aforementioned types multicomponent transformations.

Language: Английский

Synthesis of Multisubstituted Arylnitriles via Tf2O-Mediated Benzannulation of Enaminones with Acylacetonitriles DOI
Xiaohan Zhang,

Fang Li,

Yue Zhou

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 3, 2025

A novel and efficient method for the synthesis of multisubstituted arylnitriles via Tf2O-mediated [3 + 2 1] benzannulation enaminones acylacetonitriles has been developed. This reaction proceeds under mild conditions with excellent functional group compatibility. Mechanistic studies have revealed that cyclization involves two consecutive nucleophilic additions, followed by a cascade Knoevenagel condensation aromatization. Additionally, trifluoromethanesulfonate 6 identified as crucial intermediate in this process.

Language: Английский

Citations

1
De Novo Construction of Benzene Ring: Synthesis of 2,4,6‐Trisubstituted Benzophenones Using NaH Promoted Cascade Reaction of Arylmethyl Ketone and Aromatic Aldehyde DOI
Sandeep Kumar, V. Manivannan

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(6)

Published: Feb. 1, 2025

Abstract Benzannulation is one of the most important methods to construct simplest aromatic ring, i.e., benzene ring. Various efforts synthesize derivatives were already made, but they generally require some transition metal species in stoichiometric or catalytic amounts carry out this transformation which contaminates with metal‐based impurity. On other hand, reactant, alkyne used for these transformations also quite expensive nature. Keeping facts mind, a series 2,4,6‐trisubstituted benzophenones (vis‐à‐vis 1,2,4,6‐tetrasubstituted benzenes) synthesized under and solvent free conditions using simple chemicals arylmethyl ketones, aldehydes, sodium hydride. The beauty methodology that 4 6 σ all 3 π bonds ring generated within reaction vessel. Using methodology, bearing heterocyclic groups can be readily accessed.

Language: Английский

Citations

0
Multi-Auto-Tandem Reaction to Access Site-Specific Functionalized Tricyclic Furo[3,2-c]coumarins and Naphtho[2,3-b]furan-4,9-diones DOI
Xiang Liu, Hexiang Wang, Dongxin Lin

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 24, 2025

A three-component multi-auto-tandem reaction for the construction of site-specific tricyclic furo[3,2-c]coumarins via formation C-C, C-O, and C-S bonds in one step from 4-hydroxycoumarins/4-hydroxy-2-pyrones, ynals, sodium sulfinates is reported. This cascade efficiently produces a variety rare C-2-functionalized moderate to good yields under straightforward conditions. Furthermore, this protocol can be extended coupling involving 2-hydroxy-1,4-naphthoquinone, sulfinates, yielding naphtho[2,3-b]furan-4,9-dione derivatives. Notably, carbonyl group α-position ynals act as C-2 synthons specific reaction, enabling two aforementioned types multicomponent transformations.

Language: Английский

Citations

0