Base-Promoted [4 + 1 + 1] Multicomponent Tandem Cycloaddition of Ortho-Substituted Nitroarenes, Aldehydes, and Ammonium Salts To Access 2,4-Substituted Quinazoline Frameworks

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(5), P. 1982 - 1995

Published: Jan. 23, 2025

We report a base-promoted, metal-free multicomponent tandem reaction, involving [4 + 1 1] cycloaddition process between ortho-substituted nitroarenes, aldehydes, and ammonium salts. Modifying the substituents on nitroaromatic compounds effectively provides structurally diverse 2-substituted 4-alkenylquinazolines with good to excellent yields (77%-90% quinazoline 51 examples) high tolerance for various inorganic salts (13 examples, such as NH3·H2O, NH4Cl, NH4HF2). A new method constructing 2,4-substituted selectivity from simple nitrogen source was developed, reaction can be scaled up gram scale. Additionally, this also facilitates preparation of organic molecules photophysical properties, offering insights into further transformation quinazolines.

Language: Английский

Brønsted Acid Triggers [6/7 + 1] Cascade Cyclization by N-Alkyl Amine C(sp³)–N Cleavage: Mild Synthesis of Benzo[1,4]oxazepane and Dihydrobenzo[1,5]oxazocine

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13629 - 13640

Published: Sept. 2, 2024

A catalyst-free mild synthesis was reported to produce medium-ring oxazepane and oxazocine derivatives from aminomaleimides

Language: Английский

Substrate-induced Dual Utilization Cascade Reaction of N-alkyl Anilines: Highly Site-selective Sustainable Synthesis of Chromeno[4,3-b]quinolin-6-ones

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 29, 2024

A substrate-induced cleavage and reorganization cascade reaction of N -alkyl anilines as a carbon source the waste group into chromeno[4,3- b ]quinolin-6-ones.

Language: Английский