Selenylation/Cyclization of 1‐(2‐(Allyloxy)aryl)‐1H‐indoles Access to Seleno‐Benzo[2,3][1,4]oxazepino[4,5‐a]indole Derivatives DOI Open Access

Hailin Liao,

Mei Pan,

Hongrong Zhao

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 17, 2024

Abstract The iron (ІІІ)‐promoted tandem cyclization of 1‐(2‐(allyloxy)aryl)‐1 H ‐indoles with diselenides has been developed for the preparation seleno‐benzo[2,3][1,4]oxazepino[4,5‐a]indole derivatives. investigation to determine best reaction conditions indicated use (0.2 mmol) (1.5 equiv.) and iron(III) chloride in acetonitrile at room temperature under air, more than 48 examples were obtained. features access selenized 7‐membered containing nitrogen‐oxygen heterocyclic skeleton, which also represents a 7‐exo‐trig process 1‐(2‐((2‐methylallyl)oxy)aryl)‐1 diselenides.

Language: Английский

Selenium-catalyzed selective reactions of carbonyl derivatives: state-of-the-art and future challenges DOI

Xinrui Xiao,

Cheng Guan, Jie Xu

et al.

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(13), P. 4647 - 4655

Published: Jan. 1, 2021

Organoselenium-catalyzed reactions of carbonyl derivatives can produce may useful compounds under mild and green conditions. This article aims to summarize the recent advances give a perspective from both chemistry safety viewpoint.

Language: Английский

Citations

52

Photoinduced C(sp3)–H Chalcogenation of Amide Derivatives and Ethers via Ligand-to-Metal Charge-Transfer DOI
Ben Niu, Krishnakumar Sachidanandan, María Victoria Cooke

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(25), P. 4524 - 4529

Published: June 21, 2022

A photoinduced, iron(III) chloride-catalyzed C-H activation of

Language: Английский

Citations

21

2‐Benzamide Tellurenyl Iodides: Synthesis and Their Catalytic Role in CO2 Mitigation DOI
Saket Jain, Monojit Batabyal, Raviraj Ananda Thorat

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(49)

Published: June 20, 2023

Benzamide-derived organochalcogens (chalcogen=S, Se, and Te) have shown promising interest in biological synthetic chemistry. Ebselen molecule derived from benzamide moiety is the most studied organoselenium. However, its heavier congener organotellurium under-explored. Here, an efficient copper-catalyzed atom economical method has been developed to synthesize 2-phenyl-benzamide tellurenyl iodides by inserting a tellurium into carbon-iodine bond of 2-iodobenzamides one pot with 78-95 % yields. Further, Lewis acidic nature Te center basic nitrogen synthesized 2-Iodo-N-(quinolin-8-yl)benzamide enabled them as pre-catalyst for activation epoxide CO2 at 1 atm preparation cyclic carbonates TOF TON values 1447 h-1 4343, respectively, under solvent-free conditions. In addition, 2-iodo-N-(quinolin-8-yl)benzamide also used activating anilines form variety 1,3-diaryl ureas up 95 yield. The mechanistic investigation mitigation done 125 NMR HRMS studies. It seems that reaction proceeds via formation catalytically active Te-N heterocycle, ebtellur intermediate which isolated structurally characterized.

Language: Английский

Citations

11

Copper-Catalyzed and 1,3-Sulfonyl Migration Enabled Installation of Azaindoles in the Periphery of Aryl Rings: Synthesis of Sulfonylated Pyrrolo[2,3-b]quinolines and Investigation of Antimalarial Potency DOI
Shivani Choudhary,

Gayyur,

Siddhant

et al.

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

Published: April 24, 2025

Herein, an atom efficient and one-pot protocol, offering a series of sulfonylated pyrrolo[2,3-b]quinolines via C-N, C-C, C-S bond formation, has been developed with inexpensive copper catalyst. Notably, the reaction proceeds double-annulation followed by 1,3-sulfonyl migration sequence. Moreover, method is applicable to broad range 2-carbonylanilines. Furthermore, synthetic applications scale-up highlight utility potential this protocol. In addition, antimalarial property showed parasite inhibition without cytotoxic effects in mammalian cells.

Language: Английский

Citations

0

Highly selective radical isothiocyano-chalcogenization of alkenes with NH4SCN in water DOI
Chao Xu, Ze He,

Xiaokang Kang

et al.

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(19), P. 7544 - 7548

Published: Jan. 1, 2021

A sustainable, highly chemoselective, regioselective and cis -selective radical isothiocyano-chalcogenization of alkenes with NH 4 SCN in water is disclosed.

Language: Английский

Citations

25

A base-free copper-assisted synthesis of C2-symmetric spirotelluranes and biaryls based on divergent stoichiometry of Na2Te DOI
Monojit Batabyal, Saket Jain, Aditya Upadhyay

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(50), P. 7050 - 7053

Published: Jan. 1, 2022

A one pot Cu(I)-assisted synthetic methodology has been developed for the preparation of biologically important C2-symmetric spirodiaza, benzyloxy and benzoxytelluranes from 2-bromo-N-aryl benzamides, benzyl alcohols, benzoic acids by using tellurium dianion (Te2-) under base-free conditions. Furthermore, C-C coupled biaryl 1,1'-diamides have prepared an excess Na2Te same reaction The synthesized spirodiazatelluranes served as a potent catalyst reduction H2O2 nitro-Michael reactions.

Language: Английский

Citations

16

Methylselenized Glucose: Improvement of the Stability of Glucose-Supported Selenium via the End-Capping Strategy DOI
Qiyuan Wang,

Peizi Li,

Tao Li

et al.

Industrial & Engineering Chemistry Research, Journal Year: 2021, Volume and Issue: 60(24), P. 8659 - 8663

Published: June 10, 2021

In this work, the end-capping strategy was adopted in selenized material production for first time. Methylselenized glucose, as a new-generation glucose product, designed and synthesized under NaBH4-free conditions, avoiding generation of hydrogen gas. comparison with reported works, new method significantly reduced cost enhanced safety. The produced methylselenized an even more stable low-valent Se it hardly oxidized by air, resulting elevated efficiency serving practical fertilizer Se-enriched crop planting.

Language: Английский

Citations

14

FeCl3-catalyzed three-component aryl-selenylation of alkenes DOI
Chao Xu, Ze He, Hongqin Yang

et al.

Tetrahedron, Journal Year: 2021, Volume and Issue: 91, P. 132239 - 132239

Published: May 27, 2021

Language: Английский

Citations

11

Chalcogenation/pyrrolo(pyrido)annulation of 2-(3-butenyl)quinazolin-4(3H)-ones by arylsulfenyl(selenyl) chlorides DOI
А. И. Васькевич, Nataliia O. Savinchuk, Ruslan I. Vaskevych

et al.

Tetrahedron, Journal Year: 2022, Volume and Issue: 111, P. 132722 - 132722

Published: March 14, 2022

Language: Английский

Citations

8

Electrochemical Synthesis of 4‐Selenylated Oxazolones via Oxyselenylation of Ynamides DOI Open Access
Jinhui Cai,

Kaili Cen,

Weishuang Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 19, 2024

Abstract Electrosynthesis of selenylated‐oxazolone derivatives via cascade selenylation/cyclization ynamides was disclosed. A series diaryl diselenides, dialkyl and heteroaryl‐substituted tolerated in this protocol delivered 4‐selenyloxazolones 28–83% yields. The scale‐up reaction the oxidation performed to showcase practicability method. Furthermore, mechanistic experiments indicated that a cationic pathway instead radical probably involved.

Language: Английский

Citations

1