Metal‐ And Light‐Free Direct C‐3 Ketoalkylation of Quinoxalin‐2(1H)‐Ones with Cyclopropanols in Aqueous Medium DOI
Devidas A. More, Mohammad Mujahid,

M. Muthukrishnan

et al.

ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(39)

Published: Oct. 19, 2022

Abstract Direct oxidative C‐3 ketoalkylation of quinoxalin‐2(1 H )‐ones with cyclopropanols using ammonium persulfate in an aqueous medium has been achieved a moderate to good yield. The reaction does not require metals, light‐source, or catalysts facilitate the and could be efficiently utilized construct wide range biologically relevant 3‐ketoalkylated quinoxalin‐2( 1H )‐ones.

Language: Английский

Ring‐Opening Functionalization/Cyclization Reactions of Cycloalkanols under Transition‐Metal‐Free Conditions DOI

Wenjun Han,

Jun‐Long Zhan,

Fang‐Long Yang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(9)

Published: Feb. 8, 2024

Abstract Cycloalkanols ring‐opening transformation is one of the most valuable and wide area research. Among numerous methods that have been developed, transition‐metal‐free approaches attracted great interest from both chemists pharmacologists. This largely due to advantages being environmentally benign, cost‐effective operationally simple. Here we provide a comprehensive outline on recent advances in synthesis distally substituted ketones cyclic compounds via cycloalkanols under conditions.

Language: Английский

Citations

6
Visible-light-induced tandem ring opening/1,6-conjugate addition of cyclobutanols with p-quinone methides under metal- and additive-free conditions DOI

Tongyao Zhou,

Jie Zeng, Yang Liu

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(3), P. 1375 - 1380

Published: Jan. 1, 2024

A visible-light-mediated tandem ring opening/1,6-conjugate addition of cyclobutanols with p -quinone methides was developed. This protocol allowed the formation δ,δ-diaryl ketones in presence a readily available organic photocatalyst.

Language: Английский

Citations

5
Iron-catalyzed oxosulfonylation of alkynes with small-ring compounds and Na2S2O5 for the synthesis of β-keto sulfones DOI

Liu-Bin Li,

Hui Qiu,

Mu-Han Li

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(20), P. 5190 - 5197

Published: Jan. 1, 2023

An efficient and rapid iron-catalyzed oxosulfonylation of alkynes with small-ring compounds Na 2 S O 5 for the synthesis β -keto sulfones has been developed.

Language: Английский

Citations

12
Iron-Catalyzed Oxidative Rearrangement of Cyclopropanone Hemiaminals: General Access to Pyrroloindolones from Indoles DOI
Roger Machín Rivera,

Zack R. Ferrin,

Vincent N. G. Lindsay

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4738 - 4743

Published: May 29, 2024

A concise synthetic approach to medicinally relevant pyrroloindolones and related fused heterocycles is reported via the diastereoselective

Language: Английский

Citations

4
Metal-Free Approach for Oxa-spirocyclohexadienones through [3 + 2]/[4 + 2] ipso-Cyclization of para-Quinone Methides with Halo Alcohols DOI

Ramesh A. Gaikwad,

Amol T. Savekar,

Suresh B. Waghmode

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(14), P. 9987 - 10001

Published: July 5, 2023

A facile one-pot metal-free, base-mediated formal [3 + 2] and [4 dearomative ipso-cycloaddition of para-quinone methides (p-QMs) with halo alcohols has been designed for the efficient construction 2-oxa-spirocyclohexadienones in excellent yield under mild reaction conditions. The commercial availability bases, reagents, convenient procedure makes it an attractive method ipso-cyclization.

Language: Английский

Citations

10
Pd-Catalyzed Cross-Coupling of Cyclopropanols with 2-Br-p-Quinone Methides/2-Br-Cinnamate Esters Followed by a 1,6- and 1,4-Conjugate Addition Reaction DOI

Baliram B. Mane,

Amol T. Savekar,

Suresh B. Waghmode

et al.

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

Published: March 10, 2025

A novel cascade Pd-catalyzed cross-coupling reaction of cyclopropyl alcohol-derived ketone homoenolate with 2-Br-p-quinone methides and 2-Br-cinnamate esters followed by a 1,6- 1,4-conjugate addition is disclosed. This protocol converts various alcohols into homoenolate, which undergoes C-C bond formation 2-Br p-quinone esters. The salient features this methodology include its operational simplicity, mild conditions, an environmentally benign protocol, high efficiency, good to excellent yields, wide substrate scope.

Language: Английский

Citations

0
Metal free, one pot 1,6‐Conjugate Addition of Diol on para‐Quinone Methide followed by ipso cyclization: An Approach to Spiro 1,4‐Dioxane cyclohexadienone Derivatives DOI

Ramesh A. Gaikwad,

Sumit B. Kamble,

Suresh B. Waghmode

et al.

Chemistry - An Asian Journal, Journal Year: 2022, Volume and Issue: 17(24)

Published: Oct. 19, 2022

A novel one-pot transition metal-free and Brönsted acid mediated 1,6-conjugate addition of bisnuleophilic diol on biselectrophilc para-quinone methide followed by ipso cyclization assisted NBS has been developed under mild reaction conditions, offers a new approach to synthesize spiro 1,4-dioxane cyclohexadienone derivatives. This strategy features broad substrate scope p-QMs with high functional group tolerance good yields spirocyclic scaffolds (60-92 %). N-Bromo succinimide an important role in spirocyclization efficiency.

Language: Английский

Citations

12
Rh(iii)-catalyzed [4 + 1] cyclization of aryl substituted pyrazoles with cyclopropanols via C–H activation DOI
Wenxi Chen,

Yan Mao,

Min Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(4), P. 775 - 782

Published: Dec. 19, 2022

A rhodium-catalyzed formal [4 + 1]-cyclization reaction of aryl substituted pyrazoles with cyclopropanols via C-H bond activation/cyclization processes to selectively construct a series carbonyl functionalized pyrazolo[5,1-a]isoindoles is described. The features good functional group compatibility and broad substrate scope respect both cyclization components up 84% yields. Mechanistic studies indicated that the cleavage might be rate-determining step in this transformation.

Language: Английский

Citations

11
A one-pot Synthesis of 2,3-Dihydrobenzofurans, Benzofuran-2(3H)-ones, and Indoles via [4 + 1] Annulation Reaction of ortho-substituted para-Quinone Methides and Bromonitromethane DOI

Amol T. Savekar,

Vishal B. Karande,

Dattatray G. Hingane

et al.

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

Published: Jan. 1, 2024

A facile one-pot synthesis of oxygen- and nitrogen-containing benzoheterocycles has been achieved through [4 + 1] annulation para -quinone methides, followed by an oxidation/elimination sequence.

Language: Английский

Citations

2
Divergent Construction of Azaheterocycles via Alkoxyl Radical-Triggered C–C Bond Cleavage/Cyclization of N-Functionalized Acrylamides DOI
Yingjie Ma,

Zi-Hang Yuan,

Pin Gao

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(14), P. 9927 - 9940

Published: July 11, 2023

An array of redox-neutral alkylation/cyclization cascade reactions N-functionalized acrylamides with cycloalkyl hydroperoxides were achieved via the alkoxyl radical-triggered C-C bond cleavage. Through adjusting radical acceptors on N atom, a variety keto-alkylated chain-containing azaheterocycles, including indolo[2,1-a]isoquinolin-6(5H)-ones, quinoline-2,4-diones, and pyrido[4,3,2-gh]phenanthridines constructed by one-pot procedure good yields excellent functional group tolerance.

Language: Английский

Citations

4