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
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
Citations
0
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: April 23, 2025
An N-heterocyclic carbene (NHC)-catalyzed [4 + 2] annulation enables the direct synthesis of 2-pyrones from α-chlorothioesters and β,γ-unsaturated α-keto esters or chalcones. The method utilizes NHC-activated to generate key intermediates for 2-pyrone formation with high functional group tolerance. Moreover, were transformed into polysubstituted benzene naphthalene derivatives, showcasing their synthetic value.
Language: Английский
Citations
0
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 3, 2024
Morita-Baylis-Hillman (MBH) reaction, typically catalyzed by a Lewis base, is popular and useful method for C-C bond formation. Unfortunately, it limited slow reaction rate has sensitivity toward steric electronic parameters. Despite tremendous efforts, the versatility of keeps quest open new mechanistic catalytic pathways. Here, we have reported Bro̷nsted acid-catalyzed, electrophilic amination (Umpolung imine) as an inverse Aza Intramolecular MBH adduct in form 2-acylindole. Umpolung imine with nitrogen acting center been achieved. Interestingly, was also shown to occur under catalyst-free conditions also. The expected products ketimine formation, 6π electrocyclization, or quinoline formation were least/not observed. A large number examples demonstrated strength. β-aryl-substituted acrylate acrylamide (cinnamates cinnamides), which are extremely sluggish conventional chemistry, highlights developed methodology. annulated product exhibited keto-enol tautomerism, proven
Language: Английский
Citations
0
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 12, 2024
A rhodaelectro-catalyzed double dehydrogenative Heck reaction of indole-2-carboxylic acids with alkenes has been developed for the synthesis pyrano[3,4-
Language: Английский
Citations
0
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 19, 2024
We developed a method for allowing cascade cyclization of 2-nitrochalcones with pyrazoles, imidazole, and indazole in the presence CuI catalyst, DBU base, THF solvent. The conditions were tolerant an array useful functionalities including ester, nitro, cyano, halogen groups. A mechanistic consideration was also provided, as H2O2 presumably byproduct. Our appears to be rare example directly prepare C3-heterocyclic unprotected indoles.
Language: Английский
Citations
0
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
Citations
0