Synthesis of Selenocyanates and Selenoethers of Amino Pyrazoles and Amino Uracils by In Situ Triselenium Dicyanide from Malononitrile and Selenium Dioxide DOI Creative Commons
Danish Ali,

Nurabul Mondal,

Anoop Kumar Panday

et al.

ACS Omega, Journal Year: 2023, Volume and Issue: 8(28), P. 25349 - 25357

Published: July 5, 2023

Herein, we report an efficient method for synthesis of novel selenocyanates amino pyrazole, uracil, and isoxazole derivatives using in situ triselenium dicyanide from the combination malononitrile selenium dioxide DMSO medium. Using same but changing stoichiometry reagents sequence addition temperature, symmetrical selenoethers pyrazoles uracils were prepared good yields. Furthermore, utilized corresponding alkynyl selenides presence CuI Cs2CO3. The salient features this methodology are inexpensive starting materials, short reaction time, to very This is also applicable gram-scale uracils.

Language: Английский

Recent advances in the synthesis of organoselenium heterocycle conjugates DOI
Saad Shaaban,

Hussein Ba‐Ghazal,

Yasair S. Al‐Faiyz

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 157, P. 133957 - 133957

Published: March 23, 2024

Language: Английский

Citations

16

A critical review on the sustainable synthesis of pyrimidine-based heterocycles and their biological activities DOI

Viphrezolie Sorhie,

Tsenbeni N. Lotha,

Susital Mal

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134626 - 134626

Published: March 1, 2025

Language: Английский

Citations

1

Visible‐Light‐Induced Domino Cyclization to Access Pyrido[2,3‐d]pyrimidine‐2,4‐diones via a Radical‐Polar Crossover Reaction DOI

Wanqing Zuo,

Yu Cheng, Zhizhen Zhu

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(19), P. 2346 - 2350

Published: May 27, 2024

Comprehensive Summary Catalytic and green strategies for the synthesis of privileged scaffolds are synthetically appealing. We now report a radical‐polar crossover (RPC)‐enabled three‐component cyclization bromodifluoroalkyls with enaminones 6‐aminouraciles via visible‐light‐induced domino cyclization. The reaction exhibited broad substrate scope (> 40 examples) including complex molecules, which highlighted utility this strategy construction library bioactive analogs.

Language: Английский

Citations

7

CH‐Functionalization of Heterocycles with the Formation of C−O, C−N, C−S/Se, and C−P Bonds by Intermolecular Addition of Heteroatom‐Centered Radicals DOI
Alexander S. Budnikov, Igor B. Krylov, Olga M. Mulina

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(11), P. 1714 - 1755

Published: April 12, 2023

Abstract In the last decade, free radicals have found a wide application in functionalization of unsaturated compounds, such as alkenes, alkynes, and arenes, via free‐radical addition to carbon‐carbon π‐bonds. these processes, intermolecular attack on aromatic substrates represents challenge due relatively high resistance π‐system reactions comparison alkene C=C bonds. The heterocycles is especially interesting diversity their structures chemical properties well importance for medicinal chemistry, agrochemistry, materials science. Addition C‐centered widely known Minisci‐type well‐reviewed. this paper, we summarized main achievements less explored group processes: by heteroatom‐centered (O‐, N‐, S‐/Se‐, P‐radicals) with emphasis papers published after 2010. Literature analysis revealed strong trend towards usage electrochemistry photoredox‐catalysis generation recent years. remaining fundamental problem field lack experimental support proposed mechanisms frequent existence several plausible reaction pathways. progress mechanistic studies can significantly improve prediction optimal conditions depending structure.

Language: Английский

Citations

14

Multicomponent Synthesis of Fluorescent Thiazole–Indole Hybrids and Thiazole-Based Novel Polymers DOI

Prabhas Bhaumick,

Rohit Kumar, Swadhin Swaraj Acharya

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(17), P. 11399 - 11413

Published: Aug. 23, 2022

Herein, we report an efficient multicomponent reaction for the synthesis of trisubstituted thiazoles involving a one-pot C–C, C–N, and C–S bond-forming process from readily available starting materials. The arylglyoxal, indole, aryl thioamides in acetic acid medium under sealed heating conditions provided 3-(2,4-diarylthiazol-5-yl)-1H-indoles (4) good to excellent yields. Using similar strategy, thioamide, 2,5-dihydroxy-1,4-benzoquinone structurally interesting bis-thiazoles having dihydroxy-1,4-benzoquinone linker (9). All products were fully characterized by spectroscopic techniques. We also recorded single-crystal X-ray diffraction (XRD) compounds 4b 9a unambiguous structure determination. Indole-linked exhibit prominent fluorescence properties. relative quantum yields all thiazole-linked indoles measured dimethyl sulfoxide (DMSO) with respect quinine sulfate 0.1 M H2SO4 as reference. scope this was further explored preparing novel polymers 11a 11b using naphthalene/benzene-1,4-bis(carbothioamide) polymerization.

Language: Английский

Citations

21

HFIP-mediated multicomponent reactions for the synthesis of fluorescent quinoline-fused pyrroles DOI
Rohit Kumar, Swadhin Swaraj Acharya,

Prabhas Bhaumick

et al.

Tetrahedron, Journal Year: 2023, Volume and Issue: 132, P. 133250 - 133250

Published: Jan. 6, 2023

Language: Английский

Citations

13

Copper-Mediated C4-Benzylations of 5-Aminopyrazoles with 3-Indoleacetic Acids DOI
Qiwen Gao, Jinhong Tian,

Kangmei Wen

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 6623 - 6632

Published: May 11, 2023

Herein, we present a copper-mediated C4-benzylation of 5-aminopyrazoles with 3-indoleacetic acids. Various benzylated are prepared in good-to-excellent yields under basic and ligand-free conditions the presence copper acetate. Moreover, this benzylation method is applicable to other substrates, including naphthylamine, 2-aminochromen-4-one, enamines. Some products exhibit antiproliferative activities against cancer cell lines. In addition, C4-benzylated cyclized into 1H-pyrazolo[4',3':6,7]azepino[3,4-b]indoles aldehydes via one-pot two-step processes; notably, fluorescence emissions large Stokes shifts.

Language: Английский

Citations

12

Domino Reaction for the Synthesis of Pyrazole/Isoxazole Fused Naphthyridine Derivatives Involving Indole Ring Opening and Double Ring Formation DOI

Darakshan,

Tasneem Parvin

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 6847 - 6856

Published: May 9, 2023

Herein, a hitherto unreported approach for the synthesis of pyrazole/isoxazole-fused naphthyridine derivatives by three-component domino reaction arylglyoxal monohydrate, 5-amino pyrazole/isoxazole, and indoles in acetic acid medium has been reported. In this method, four bonds (2 C-C 2 C-N) form one-pot with concomitant formation two new pyridine rings via indole ring opening double cyclization reactions. This methodology is also applicable gram-scale synthesis. The mechanism was studied isolating characterizing intermediates. Along complete characterization all products, structure product 4o unambiguously confirmed single crystal X-ray diffraction.

Language: Английский

Citations

11

Transition-Metal-Free Dehydrogenation of Benzyl Alcohol for C–C and C–N Bond Formation for the Synthesis of Pyrazolo[3,4-b]pyridine and Pyrazoline Derivatives DOI
Sesuraj Babiola Annes,

Karuppaiah Perumal,

Kalaiselvan Anandhakumar

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 6039 - 6057

Published: April 26, 2023

A series of cascade reactions that produce a range functionalized aromatic heterocyclic compounds with pyrazole/pyrazoline cores have been developed. The method relies on metal-free dehydrogenative process to in-situ benzaldehydes. produced benzaldehyde was then allowed react some other substances, including acetophenone, pyrazole amine, and phenylhydrazine. intermediate from these substrates underwent several chemical processes, electrocyclization, the aza-Diels-Alder reaction, formation intramolecular C-N bonds. These positive outcomes would open up possibility producing biologically active pyrazolo[3,4-b]pyridine pyrazoline derivatives through variety possible reactions.

Language: Английский

Citations

9

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

9