Copper-Catalyzed Cascade Cyclization of 2-Nitrochalcones with NH-Heterocycles DOI
Thang M. Ly, Tan N. Huynh, Nam Phan

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 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.

Язык: Английский

Base-Catalyzed Cascade Cyclization of 2-Nitrochalcones and Isocyanides to Access Pyrano[3,4-b]indol-1(9H)-one Frameworks DOI
Juan Wan,

Guiyun Zeng,

Shuntao Huang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4549 - 4559

Опубликована: Март 22, 2024

An unexpected cascade reaction of 2-nitrochalcones with isocyanoacetates has been reported for the efficient synthesis indole carboxylic esters and pyranoindoles. The conversion was achieved by KOH-catalyzed cyclization elimination nitro group final decarbonylation–aromatization. method used to synthesize a series potentially biologically active derivatives (49 examples) in 67–85% yields under transition-metal-free catalytic conditions.

Язык: Английский

Процитировано

6

One-pot FeCl3-catalyzed sustainable synthesis of pyrimidines using ammonium iodide, aldehydes and alkyl lactate as raw materials DOI

Meitian Fu,

Jingpeng Li, Zhou Zhang

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(15), С. 8854 - 8860

Опубликована: Янв. 1, 2024

Iron( iii )- and iodide-promoted efficient synthesis of pyrimidines from biomass-based alkyl lactates, inorganic ammonium, aldehydes was carried out.

Язык: Английский

Процитировано

4

Elemental Sulfur-Mediated Aromatic Halogenation DOI
Junpei Matsuoka,

Yuna Yano,

Yuuka Hirose

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 89(1), С. 770 - 777

Опубликована: Дек. 19, 2023

A method for aromatic halogenation using a combination of elemental sulfur (S8) and N-halosuccinimide has been developed. catalytic quantity with N-bromosuccinimide (NBS) N-chlorosuccinimide (NCS) effectively halogenated less-reactive compounds, such as ester-, cyano-, nitro-substituted anisole derivatives. No reaction occurred in the absence S8, underscoring its crucial role activity. This system was also applicable to iodination 1,3-diiodo-5,5-dimethylhydantoin.

Язык: Английский

Процитировано

9

Substrate‐induced Selective α‐C(sp3)−H Activation of N‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air DOI
Zhou Zhang, Juan Wan, Lu Yin

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(6), С. 1430 - 1435

Опубликована: Янв. 23, 2024

Abstract A substrate‐induced synthesis of coumarin‐fused quinolinones is achieved from 4‐(phenylamino)‐2 H ‐chromen‐2‐ones using N ‐alkyl amines as the solvent and a carbon source under air conditions without any catalysts in one pot. This protocol highlights special roles which were not only used reactants but also an internal oxidant selectively activated ‐ α ‐C( sp 3 )−H bond. reaction features catalyst‐free, broad substrate scopes ( 27 examples 24 examples), operationally simple for one‐step synthesis, recovery recycling solvent.

Язык: Английский

Процитировано

3

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

Guiyun Zeng,

Juan Wan,

Yilong Yuan

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(5), С. 1982 - 1995

Опубликована: Янв. 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.

Язык: Английский

Процитировано

0

Base-Catalyzed Chalcogenative Annulation of N-Maleimido O-Aminobenzyl Alcohol with Elemental Sulfur/Selenium: Access to 1,4-Sulfa-/Selena-zepanes DOI

Yuanmin Wen,

Teng Liu,

Shuntao Huang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 17, 2025

We reported an unprecedented chalcogen element (Se, S) insertion reaction with functionalized aminomaleimide to assemble medium-sized nitrogen-containing organic selenium/sulfur catalyzed by bases. During these [5/6 + 1] tandem annulations, a variety of low-valent inorganic chalcogenides exhibited excellent compatibility, providing wide scope structurally diverse 1,4-selenazepanes (17 examples, 60–71% yields), 1,4-benzothiazepines (20 74–86% and 1,4-thiazines (6 31–68% yields). The characteristics this transformation are high atomic economy, formation two C–Se or C–S bonds in one step, avoiding the use unstable toxic reagents under mild conditions.

Язык: Английский

Процитировано

0

Base-Promoted and Copper(I)-Catalyzed Tandem Cyclization-C(sp2)-N Coupling of Vinyl Malononitriles with Ortho-Nitrochalcones: Access to Acridones and their Fused Derivatives DOI

Raju Lal Dhakar,

S Banuprakash Goud,

Sampak Samanta

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 28, 2025

An efficient Cs2CO3-promoted and copper(I)-catalyzed double cyclization of ortho-nitrochalcones with vinyl malononitriles for the de novo access to a variety tri- tetra-substituted acridones their fused derivatives value-added CN group has been developed first time. This one-pot operation proceeds through Michael-cyclization-aromatization, followed by regioselective ipso-amination via nucleophilic aromatic substitution (SNAr) reaction, resulting in two C═C bonds C-N bond acridone ring synthesis. economic strategy based on 100% carbon atoms ensures successive formation rings operation, good high yields, wide range substrates, tolerance functionalities. In addition, were converted into several acridines, highlighting synthetic versatility usefulness prepared derivatives.

Язык: Английский

Процитировано

0

DABCO Mediated Sulfur Activation‐Intramolecular De‐Nitration Strategy for the Synthesis of Novel Dihydrothiochromeno[4,3‐c]pyrazoles DOI

Deepika,

Avijit Kumar Paul, Chandi C. Malakar

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(9)

Опубликована: Июль 24, 2023

Abstract A facile and highly efficient metal‐free approach has been unfolded for the synthesis of novel dihydrothiochromeno[4,3‐ c ]pyrazoles using elemental sulfur as a powerful sulfurating reagent. This method includes sp 2 C−H functionalization followed by C−NO group displacement an odourless source activated DABCO in DMSO. Using developed synthetic strategy, library 29 ]pyrazoles, incorporating two pharmacologically important scaffolds synthesized 52–76% yield with broad substrate scope. sensible mechanistic proposal projected based on control experiments.

Язык: Английский

Процитировано

8

Microwave‐assisted Four‐component Cascade Reaction: One‐pot Rapid Access in the Metal‐free Synthesis of Fully Substituted Pyrroles DOI
Zhou Zhang, Jingpeng Li,

Zhuoyu Wang

и другие.

ChemistrySelect, Год журнала: 2023, Номер 8(36)

Опубликована: Сен. 21, 2023

Abstract A simple and rapid methodology for the synthesis of fully substituted pyrroles was accomplished by reaction microwave‐assisted from amines, 4‐hydroxycoumarins, ketones. This protocol proceeds via ketones Csp 3 −H oxidation Michael addition/ cyclization/ aromatization four‐component cascade affording pyrrole in moderate to excellent yields only min. Simple conditions, high yields, compatibility are advantages this protocol.

Язык: Английский

Процитировано

3

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

Sihan Zhao,

Yuanmin Wen

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 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.

Язык: Английский

Процитировано

0