Silver-catalyzed three-component reaction of uracils, arylboronic acids, and selenium: synthesis of 5-arylselanyluracils DOI Creative Commons
Yuki Murata,

Saori Tsuchida,

Rena Nezaki

et al.

RSC Advances, Journal Year: 2022, Volume and Issue: 12(23), P. 14502 - 14508

Published: Jan. 1, 2022

Herein, we describe a simple and general multi-component synthesis of 5-arylselanyluracils by the regioselective C-H selenation uracils. Reactions uracils with arylboronic acid Se powder in presence AgNO3 (10 mol%) at 120 °C under aerobic conditions afforded various 5-arylselanyluracils. The source introduced selanyl group was prepared from commercially available reaction system, thereby ensuring efficient protocol. This represents first example 5-arylselanyluracil system.

Language: Английский

Enantioselective Synthesis of Dihydropyrazolo[3,4‐b]pyridin‐6‐ones via N‐Heterocyclic Carbene Catalyzed [3+3] Cycloaddition of α‐Bromoenals with 5‐Aminopyrazoles DOI
Yarui Li,

Xiaoxia Huang,

Jieyin He

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(4), P. 490 - 495

Published: Jan. 24, 2023

Abstract An N‐heterocyclic carbene (NHC) catalyzed asymmetric [3+3] annulation of α ‐bromoenals with 5‐aminopyrazoles is described. Using the established methodology, a structurally diverse set high value dihydropyrazolo[3,4‐ b ]pyridine‐6‐ones were efficiently constructed in yields (up to 99%) excellent enantioselectivities >99%). The easily available starting materials, broad substrate scope, mild reaction conditions, yield and enantioselectivity make this strategy attractive for construction pyrazolo‐fused pyridone derivatives. magnified image

Language: Английский

Citations

8

Catalyst- and metal-free C(sp2)–H bond selenylation of (N-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature DOI Creative Commons
José S. S. Neto, Isis Juliane Arantes Granja, Marcos R. Scheide

et al.

Scientific Reports, Journal Year: 2023, Volume and Issue: 13(1)

Published: Aug. 31, 2023

In this paper, we report an eco-friendly approach for the C(sp2)-H bond selenylation of imidazopyridines and other N-heteroarenes as well simple arenes at ambient temperature. This new protocol consists reaction between (N-hetero)-arenes diorganyl-diselenides trichloroisocyanuric acid (TCCA)-ethanol reagent system. a short time, desired selenylated products were obtained regioselectively in good yields, with tolerance wide range functional groups.

Language: Английский

Citations

8

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery DOI
Sergey M. Desenko, Nikolay Yu. Gorobets, В. В. Липсон

et al.

The Chemical Record, Journal Year: 2023, Volume and Issue: 24(2)

Published: Sept. 5, 2023

Dihydroazolopyrimidines are an important class of heterocycles that isosteric to natural purines and therefore great interest primarily as drug-like molecules. In contrast the heteroaromatic analogs, synthetic approaches these compounds were developed much later, their chemical properties biological activity have not been studied in detail until recently. review, different ways build dihydroazolopyrimidine systems from building blocks described - via initial formation a partially hydrogenated pyrimidine ring or azole ring, well one-pot assembly azine fragments. Special attention is given modern approaches: multicomponent reactions, green chemistry, use non-classical activation methods. Information on dihydroazolopyrimidines prospects for design drugs various profiles also summarized this review.

Language: Английский

Citations

8

Synthesis of β‐Hydroxyselenides via Electrochemical Hydroxyselenenylation of Alkenes with Diselenides and H2O DOI
Weiwei Li, Yingyuan Hu,

Junsheng Hou

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(5)

Published: Feb. 2, 2024

Abstract A practical electrochemical method for the synthesis of β‐hydroxyselenides has been developed under an external oxidant‐free condition at room temperature air from alkenes with diselenides and H 2 O. radical mechanism is proposed this transformation gram‐scale reactions demonstrate practicability reaction.

Language: Английский

Citations

3

Synthesis and Application Dichalcogenides as Radical Reagents with Photochemical Technology DOI Creative Commons

Cairong Wang,

Yan Zhang, Kai Sun

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(4), P. 1998 - 1998

Published: Feb. 20, 2023

Dichalcogenides (disulfides and diselenides), as reactants for organic transformations, are important widely used because of their potential to react with nucleophiles, electrophilic reagents, radical precursors. In recent years, in combination photochemical technology, the application dichalcogenides stable reagents has opened up a new route synthesis various sulfur- selenium-containing compounds. this paper, synthetic strategies disulfides diselenides applications technology reviewed: (i) Cyclization alkenes alkynes; (ii) direct selenylation/sulfuration C−H/C−C/C−N bonds; (iii) visible-light-enabled seleno- sulfur-bifunctionalization alkenes/alkynes; (iv) Direct construction C(sp)–S bond. addition, scopes, limitations, mechanisms some reactions also described.

Language: Английский

Citations

8

Synthesis of Highly Fluorescent Thiazole Fused Benzo[a] Carbazoles by Sunlight Driven Photocyclization of Indolylthiazoles DOI Creative Commons

Prabhas Bhaumick,

Nurabul Mondal,

Lokman H. Choudhury

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 19, 2024

Abstract Herein we report for the first time a sunlight‐driven, irreversible photocyclization reaction of indole‐linked trisubstituted thiazoles, synthesis highly fluorescent thiazole‐fused benzo[ ]carbazoles using mixture solvents (CH 3 CN: DMSO; : 1). Ring opening indole moiety was observed in case thiazole derivatives having 2‐methyl substituents. Under similar conditions, thiazoles cyclic 1,3‐dicarbonyls place also worked. This provides products two medicinally important moieties and benzocarbazoles. We have studied photophysical properties all found that most synthesized very good fluorescence quantum yields.

Language: Английский

Citations

2

Visible light induced regioselective C-3 thiocyanation of imidazoheterocycles through naphthalimide dye based photoredox catalysis DOI
Pallavi Saha, Rohit Kumar, Samarpita Das

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(42), P. 8471 - 8476

Published: Jan. 1, 2023

A visible light induced C-3 thiocyanation of imidazo[1,2-a]pyridines by using a naphthalimide based photoredox catalyst has been reported. Tolerance electron withdrawing and donating groups at different positions the imidazo[1,2-a]pyridine ring led to wide substrate accessibility this method. This methodology is further reproducible with other heterocycles like benzo[d]imidazo[2,1-b]thiazoles, indoles, azaindoles, anilines.

Language: Английский

Citations

6

Dimethyl Sulfoxide-Assisted, Iodine- and Ascorbic Acid-Catalyzed One-Pot Synthetic Approach for Constructing Highly Substituted Pyrazolo[1,5-a]quinoline Thioether Derivatives DOI
Rajendhiran Saritha, Sesuraj Babiola Annes,

Karuppaiah Perumal

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 13856 - 13872

Published: Oct. 10, 2022

A dimethyl sulfoxide-assisted and iodine/ascorbic acid-catalyzed simple approach to pyrazolo[1,5-a]quinoline thioether derivatives 22 is described. The compounds were identified using 1H NMR, 13C high-resolution mass spectrometry, single-crystal X-ray diffractometry. was synthesized in a stepwise fashion through aryl sulfenylation benzannulation strategies. generated heteroaryl 23 exposed the path produce 22. reaction proceeds by way of diazotization pyrazole amine derivative 23, radical generation removal nitrogen, eventually trapping with support phenylacetylene 19. catalytic amount ascorbic acid aided reaction. There several other control studies conducted, including reactions isopropenyl acetate, tetramethylpiperidine N-oxyl reactions, without phenylacetylene. Since change substitution has previously demonstrated substantial bioactivity, core structure evaluated for functional group tolerance. reasonable mechanism then proposed, accompanied experiments scope. Suzuki used create an aryl/heteroaryl compound 35 from one 22b. In controlled oxidation paths, molecule 22a selectively transformed into corresponding sulfoxide 32 sulfone 33.

Language: Английский

Citations

9

The O2-Mediated Cross-Dehydrogenative Coupling: Rose Bengal-Catalyzed Direct Oxidative α-Acyloxylation of Ketones DOI

Yunsheng Zhu,

Shengjie Song,

Lijun Zheng

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(26), P. 4918 - 4922

Published: June 28, 2023

A general and facile approach for the direct oxidative α-acyloxylation of ketones using molecular oxygen as oxidant is developed. This method avoids use excessive peroxides expensive metal catalysts, affording a variety α-acyloxylated in satisfactory yields. Experimental studies indicate that reaction proceeds via radical pathway. Additionally, α-hydroxy could be obtained by changing solvent.

Language: Английский

Citations

5

Photocatalyst-Free Visible-Light-Promoted C–H Selenylation of Pyrazolo[1,5-a]pyrimidines DOI
Avik Kumar Bagdi, Papiya Sikdar,

Tathagata Choudhuri

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(21), P. 3693 - 3699

Published: July 6, 2023

Abstract A new method has been developed for the C–H selenyl­ation of pyrazolo[1,5-a]pyrimidine derivatives under irradiation visible light. This photocatalyst-free strategy is applicable to a wide range pyrazolo[1,5-a]pyrimidines with broad functionalities. The salient features are mild reaction conditions, use bench-stable oxidant, high regioselectivity, and scalability.

Language: Английский

Citations

5