I2/DMSO-Catalyzed Transformation of N-tosylhydrazones to 1,2,3-thiadiazoles DOI Creative Commons
Weiwei Li, Jun Zhang, Jing He

et al.

Frontiers in Chemistry, Journal Year: 2020, Volume and Issue: 8

Published: June 12, 2020

An iodine/DMSO catalyzed selective cyclization of N-tosylhydrazones with sulfur without adding external oxidant was developed for the synthesis 4-aryl-1,2,3-thiadiazoles. In this reaction, oxidation HI by using DMSO as dual and solvent is key, which allowed regeneration I2, ensuring thus success synthesis. This protocol features simple operation, high step-economy (one-pot fashion), broad substrate scope well scale-up ability.

Language: Английский

Brønsted Acid Catalyzed One-Pot Benzannulation of 2-Alkenylindoles under Aerial Oxidation: A Route to Carbazoles and Indolo[2,3-a]carbazole Alkaloids DOI
Shuvendu Saha, Ankush Banerjee, Modhu Sudan Maji

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 20(21), P. 6920 - 6924

Published: Oct. 25, 2018

A one-pot, protecting-group-free benzannulation of 2-alkenylindoles with readily available 1,3-dicarbonyls is demonstrated to construct structurally diverse carbazoles. The use a cheap Brønsted acid catalyst and air as the sole oxidant exemplifies economic viability this protocol. execution four different reactions successively generate medicinally important indolocarbazole core also achieved. This one-pot method paved way for total synthesis three alkaloids, namely staurosporinone, arcyriaflavin A, 7-hydroxy-K252c.

Language: Английский

Citations

46

Practical Approach for Clean Preparation of Z-β-Thiocyanate Alkenyl Esters DOI
Chao Wu,

Lin Hong,

Hui Shu

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2019, Volume and Issue: 7(9), P. 8798 - 8803

Published: April 11, 2019

A practical and eco-friendly method for the clean preparation of a variety Z-β-thiocyanate alkenyl esters via lactic acid-catalyzed multicomponent hydrothiocyanation reaction was established. In subgram-scale synthesis, were exclusively generated, product could be easily isolated in high purity extraction. large-scale pure products simply collected through liquid–liquid separation. The acid played dual function transformation, serving as recyclable biomass catalyst medium.

Language: Английский

Citations

42

Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds DOI
Wenbo Huang, Jing Xu, Changhui Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 84(5), P. 2941 - 2950

Published: Feb. 6, 2019

2,3-Disubstituted benzofurans were synthesized from acrolein dimer and 1,3-dicarbonyl compounds by using N-bromosuccinimide as an oxidizing agent. The method was used to synthesize two commercial drug molecules, benzbromarone amiodarone. proposed mechanism of the reaction involves a (NBS)-assisted autotandem catalysis with Lewis acid catalyst. To proof mechanism, intermediate isolated successfully, which can be converted 4,5,6,7-tetrahydrobenzofurans.

Language: Английский

Citations

35

Synthesis of a novel and reusable biological urea based acidic nanomagnetic catalyst: Application for the synthesis of 2‐amino‐3‐cyano pyridines via cooperative vinylogous anomeric based oxidation DOI
Morteza Torabi, Meysam Yarie, Mohammad Ali Zolfigol

et al.

Applied Organometallic Chemistry, Journal Year: 2019, Volume and Issue: 33(6)

Published: April 29, 2019

In the current study, a novel and reusable biological urea based nano magnetic catalyst namely Fe 3 O 4 @SiO 2 @(CH ) ‐urea‐benzimidazole sulfonic acid was designed synthesized. The structure of titled fully characterized using several skills including Fourier transform infrared (FT‐IR) spectroscopy, energy dispersive X‐ray (EDX) analysis, diffraction (XRD), scanning electron microscopy (SEM), transmission (TEM), thermo gravimetric analysis/differential thermal analysis (TG/DTG) vibrating sample magnetometer (VSM). Then, catalytic performance successfully inspected towards multicomponent synthesis 2‐amino‐3‐cyano pyridine derivatives through vinylogous anomeric oxidation pathway.

Language: Английский

Citations

34

Facile and expedient synthesis of α,β-unsaturated isoxazol-5(4H)-ones under mild conditions DOI
Fatemeh Ghorbani, Hamzeh Kiyani, Seied Ali Pourmousavi

et al.

Research on Chemical Intermediates, Journal Year: 2019, Volume and Issue: 46(1), P. 943 - 959

Published: Oct. 9, 2019

Language: Английский

Citations

34

Selective and effective anticancer agents: Synthesis, biological evaluation and structure–activity relationships of novel carbazole derivatives DOI
Wenbo Huang, Zilin Gao, Zhigang Zhang

et al.

Bioorganic Chemistry, Journal Year: 2021, Volume and Issue: 113, P. 104991 - 104991

Published: May 18, 2021

Language: Английский

Citations

24

2-Alkynyl Indole-3-carbonitriles: Synthon for the Regioselective Synthesis of Functionalized 4-Aminocarbazoles DOI
D. K. Panda,

Shivam A. Meena,

Manvi Sharma

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 26, 2025

An operationally easy and atom-economical approach for the regioselective tandem synthesis of functionalized 4-aminocarbazoles from easily accessible 2-alkynyl indole-3-carbonitriles under mild reaction conditions has been developed. The developed chemistry involves aza-Henry successive annulation to afford carbazoles. Replacement nitromethane with acetophenone led formation corresponding amino(phenyl)methanone-substituted carbazoles, further extending diversity chemistry. methodology accommodates wide functional group variation on alkyne is successfully applied late-stage modification bioactive molecules.

Language: Английский

Citations

0

Cu(I)-/Base-Mediated Domino [5 + 3 + 1] Annulation for Highly π-Extended Carbazole Frameworks and DFT Mechanistic Insights DOI
Tej Narayan Poudel, Sangita Karanjit, Hari Datta Khanal

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 20(18), P. 5648 - 5652

Published: Sept. 4, 2018

An efficient synthesis of highly π-extended carbazoles is described via an unexpected domino [5 + 3 1] annulation approach. The Cu(I)-/base-promoted reactions 2-nitrocinnamaldehydes with benzyl cyanides provide diverse benzo[b]carbazoles. reaction proposed to proceed a sequential Michael addition/intramolecular addition enol into nitro group, 6π- electrocyclization, and the final oxidative aromatization as supported by density functional theory calculations. Some synthesized showed significant potential in fluorescence sensing Cu2+ ions.

Language: Английский

Citations

29

Metal-Free Double Csp2–H Bond Functionalization: Strategy for Synthesizing Benzo[a]carbazoles from 2-Arylindoles and Acetophenones/Alkynes DOI
Penghui Ni, Jing Tan, Wenqi Zhao

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(10), P. 3687 - 3691

Published: April 30, 2019

A metal-free strategy for the synthesis of benzocarbazoles from 2-arylindoles and aryl ketones is developed. Various 2-aryl-3-vinyl-indoles were generated in situ through dehydrative condensation indoles. These key intermediates could be selectively converted into corresponding benzo[a]carbazoles via a direct cyclization process between two Csp2–H bonds. Furthermore, terminal alkynes also used as versatile C2 source to afford products good yields.

Language: Английский

Citations

29

Novel Non‐toxic and Non‐hazardous Solvent Systems for the Chemistry of Indoles: Use of a Sulfone‐containing Brønsted Acid Ionic Liquid Catalyst in Butyl Acetate DOI
Ahmed El‐Harairy,

Yiliqi,

Mei‐E Yue

et al.

ChemCatChem, Journal Year: 2019, Volume and Issue: 11(17), P. 4403 - 4410

Published: June 19, 2019

Abstract Dipolar and aprotic solvents are often required in acid‐catalyzed reactions, however, many of them listed solvent selection guides as not‐recommended due to their toxicity or explosivity. A catalytically functionalized ionic liquid, namely a sulfone‐containing imidazolium‐based Brønsted acid was synthesized. It alleviates the detrimental effect classical dipolar because this liquid integrates function able stabilize carbocation intermediates activating strong on electrophiles. The use tailor‐made exemplified some transformation reactions indoles, which proceeded with high yield selectivity using green an industrially acceptable solvent, butyl acetate. recyclability catalyst also demonstrated.

Language: Английский

Citations

29