Phosphine-catalyzed synthesis of (Z)-N-alkenyl-2-pyridones: A dual Z-diastereoselective and N-selective approach under mild conditions DOI
Nan Wang, Yuan‐Yuan Huang, Mengke Wang

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 166, P. 134206 - 134206

Published: Aug. 22, 2024

Language: Английский

Solvent- and Catalyst-Controlled Regioselective O- and N-Alkylation of 2-Pyridones by 2H-Azirines DOI
Subrata Biswas, Surajit Duari, Srabani Maity

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(20), P. 15091 - 15102

Published: Oct. 7, 2024

The synthesis of O-substituted 2-hydroxypyridines and N-substituted 2-pyridones, crucial for many bioactive compounds drugs, faces challenges due to the tautomeric nature which complicates selective alkylation. Here we developed an efficient method regioselective O- N-alkylation 2-pyridones using Bro̷nsted acid-catalyzed ring opening 2H-azirines. process involves triflic acid O-alkylation p-toluenesulfonic N-alkylation, achieving high yields under optimized conditions. For O-alkylation, a variety 2H-azirines were used, resulting in significant desired products. Similarly, conditions produced excellent yields, highlighting method's versatility. This methodology was further demonstrated through scaled-up syntheses subsequent transformations, showcasing its practicality complex molecular architectures. proposed mechanism protonation 2H-azirine, followed by SN2-type attack hydrolysis, leading alkylated innovative approach, emphasizing catalysis careful control reaction conditions, represents advancement alkylation with broad implications medicinal chemistry.

Language: Английский

Citations

2
Palladium-Catalyzed anti-Michael-Type Hydroamination of N-(Quinolin-8-yl)acrylamide with 2-Pyridones DOI
Hirotsugu Suzuki,

Soma Yamanokuchi,

Ryota Moro

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6444 - 6448

Published: July 24, 2024

Here we report a palladium-catalyzed

Language: Английский

Citations

1
Synthesis of acyclic nucleoside analogues through P(NMe2)3-Mediated regioselective N-alkylation DOI
Ke‐Xin Huang, Zhaoyang Chen,

Xueguo Liu

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 162, P. 134126 - 134126

Published: July 4, 2024

Language: Английский

Citations

0
Efficient Synthesis of Cyanohydrin Esters: P(NMe2)3 Mediated Direct Deoxygenation of Acyl Cyanides with Carboxylic Acids DOI
Yuan‐Yuan Huang, Nan Wang, Mengke Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11777 - 11782

Published: Aug. 8, 2024

An efficient synthesis of cyanohydrin esters via a P(NMe2)3 mediated direct deoxygenation process has been exploited, circumventing the release or transformation CN─ anion during reaction. This approach possesses broad scope and acts as powerful supplement for construction diverse esters. It offers advantages such mild conditions, straightforward operations, excellent scalability, affirming feasibility versatility this highlighting its potential in practical synthesis.

Language: Английский

Citations

0
An Efficient Method for Thioesterification of Carboxylic Acid with Sulfenylchloride DOI
Jia-Hong Chen, Mengke Wang, Weichun Huang

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: unknown, P. 134422 - 134422

Published: Dec. 1, 2024

Language: Английский

Citations

0
Phosphine-catalyzed synthesis of (Z)-N-alkenyl-2-pyridones: A dual Z-diastereoselective and N-selective approach under mild conditions DOI
Nan Wang, Yuan‐Yuan Huang, Mengke Wang

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 166, P. 134206 - 134206

Published: Aug. 22, 2024

Language: Английский

Citations

0