Multicomponent Synthesis of S-Benzyl Dithiocarbamates from para-Quinone Methides and Their Biological Evaluation for the Treatment of Alzheimer’s Disease

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(10), P. 6730 - 6741

Published: May 12, 2022

Multicomponent synthesis of biologically relevant S-benzyl dithiocarbamates from para-quinone methides, amines, and carbon disulfide are described under catalyst additive-free conditions. The reactions proceeded at room temperature in a short span time with excellent yields. One the synthesized compounds, 3e showed considerable acetylcholinesterase (AChE) inhibitory (51.70 + 5.63% 20 μm) antioxidant (63.52 ± 1.15 activities.

Language: Английский

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Photocatalytic N‐Alkylation of NH‐Sulfoximines via Anti‐Markovnikov Hydroamination of Alkenes

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(21), P. 3666 - 3673

Published: Sept. 14, 2023

Abstract Sulfoximines, the isoelectronic with sulfones, represent a class of alternative and intriguing motifs in both discovery program agrochemistry. N ‐Alkylation on imines could significantly improve their bioactivities, but lack general method has hindered further uptake by medicinal chemistry drug development. Herein, we present mild photocatalytic anti‐Markovnikov hydroamination alkenes to construct ‐alkylated sulfoximines broad substrate tolerance primary, secondary tertiary alkyl substituents as well diverse range sulfoximines. The mechanistic studies support pathway, demonstrate that alkene radical cation rather than iminium serves key intermediate transformation.

Language: Английский

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1,6-Conjugate addition of in situ generated aryldiazenes to p-quinone methides

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(27), P. 5636 - 5645

Published: Jan. 1, 2024

Herein we report a transition-metal free, base-mediated 1,6-conjugate addition of aryldiazenes to para -quinone methides ( p -QMs).

Language: Английский

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Synthesis of Sulfoximines and Cyclic Sulfoximines

Published: Jan. 1, 2025

Language: Английский

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Multicomponent Synthesis of Biologically Relevant S‐Diarylmethane Dithiocarbamates Using p‐Quinone Methides

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(9), P. 1549 - 1554

Published: March 16, 2022

Abstract A metal and base‐free, operationally simple, scalable multicomponent approach towards the synthesis of S ‐diarylmethane dithiocarbamates is reported. range structurally electronically diverse p ‐quinone methides are shown to react with a variety amines, carbon disulfide furnish corresponding in good excellent yields under mild conditions. Furthermore, ‐QMs embedded aliphatic substituents well accommodated. Importantly, these readily accessible compounds demonstrated promising anti‐proliferative activity low micromolar ranges lung adenocarcinoma cells, reiterating importance developed methodology. magnified image

Language: Английский

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Directed Palladium‐Catalyzed pseudo‐Anomeric C−H Functionalization of Glycal‐Type Substrates: Access to Unsymmetrical gem‐Diarylmethyl C‐Glycosides

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(6), P. 820 - 825

Published: Feb. 22, 2023

Pd(II)-Catalyzed, bidentate directing group (BDG)-assisted C(sp2)−H functionalization of C2-amido glycals onto the anomeric position is described as a contemporary method for construction various unsymmetrical gem-diarylmethyl C-glycosides. Thanks to amidoquinoline-type group, insertion diverse para-quinone methides (p-QMs) pseudo-anomeric glycal substrates were executed in moderate good yields. Further final product can be successfully demonstrated by known palladium-catalyzed cross-coupling reactions. As service our authors and readers, this journal provides supporting information supplied authors. Such materials are peer reviewed may re-organized online delivery, but not copy-edited or typeset. Technical support issues arising from (other than missing files) should addressed Please note: The publisher responsible content functionality any Any queries content) directed corresponding author article.

Language: Английский

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Electrochemical Reductive Carboxylation of para‐Quinone Methides with CO₂

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(22), P. 3830 - 3836

Published: Oct. 6, 2023

Abstract Herein, electrochemical reductive carboxylation of para ‐quinone methides with CO 2 was developed. A variety value‐added carboxylic acids can be accessed in moderate to excellent yields. Preliminary studies showed that were reduced benzyl carbanion during the reaction. This protocol features high atom economy, operational simplicity, and environmental friendliness, enabling synthesis various compounds.

Language: Английский

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Atom-Economic Synthesis of Unsymmetrical gem-Diarylmethylthio/Seleno Glycosides via Base Mediated C(O)–S/Se Bond Cleavage and Acyl Transfer Approach of Glycosylthio/Selenoacetates

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(3), P. 1695 - 1712

Published: Jan. 12, 2023

Herein, we invented the Cs2CO3-mediated atom economic method that streamlines scission of C(O)–S/Se bond involving in situ generation an anomeric thiolate/selenolate anion, which reacted with p-QMs to yield novel unsymmetrical gem-diarylmethylthio/seleno glycosides while retaining stereochemistry. Notably, key features this protocol involve unprecedented long-range acyl transfer (from S/Se O), thus affording acylation final product is not yet reported by classical methods. This straightforward offers a mild, short reaction time, synthetically simple approach, and compatibility 8 types sugar along phenylthio/benzylseleno esters.

Language: Английский

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TEMPO-Mediated Synthesis of Indolyl/Imidazo[1,2-a]pyridinyl-Substituted para-Quinone Methides from Butylated Hydroxytoluene

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(23), P. 17090 - 17100

Published: Nov. 11, 2021

A series of indolyl or imidazo[1,2-a]pyridinyl-substituted para-quinone methides (p-QMs) is prepared by a metal-free, TEMPO-mediated cross-dehydrogenative coupling butylated hydroxytoluene (BHT) with indoles imidazo[1,2-a]pyridines in good to high yields. Broad substrate scope respect and imidazo[1,2-a]pyridines, functional group tolerance, acid/base-free conditions are advantageous feature the developed protocol. The method was amenable for scale-up on gram scale. Based control experiments, reaction mechanism proposed describe this transformation.

Language: Английский

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Lewis acid triggered N-alkylation of sulfoximines through nucleophilic ring-opening of donor–acceptor cyclopropanes: synthesis of γ-sulfoximino malonic diesters

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(12), P. 2518 - 2529

Published: Jan. 1, 2022

Scandium triflate (Sc(OTf)3) catalyzed, mild, and regioselective ring-opening reaction of donor-acceptor (D-A) cyclopropanes has been developed using sulfoximines for the synthesis γ-sulfoximino malonic diesters. This protocol allows different N-alkyl in good to excellent yields (up 94%) with broad functional group tolerance. In this process, N-H C-C bonds are cleaved form new C-N C-H bonds. The feasibility method is supported by a gram-scale synthetic elaboration obtained product.

Language: Английский

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