One-pot three-component synthesis of azaspirononatriene derivatives DOI Creative Commons

Ali Oudi,

Abbas Ali Esmaeili, Azizollah Habibi

et al.

Scientific Reports, Journal Year: 2025, Volume and Issue: 15(1)

Published: April 30, 2025

The present investigation has introduced a new class of isocyanide/acetylene-based multicomponent reactions (IAMCRs). These are robust technique for efficiently synthesizing intricate spiro architectures through zwitterionic adduct. coupling reaction between the "in situ" generated dipoles isocyanide-acetylenic ester adducts and 3-alkyl-4-arylidene-isoxazol-5(4H)-one derivative presents highly effective synthetic pathway obtaining novel 1-oxo-2-oxa-3-azaspiro[4.4]nona-3,6,8-triene heterocycles. broad range substrates, standard experimental conditions, straightforward procedure, impressive yields make our catalyst-free three-component approach practical green, as it remarkably offers step-, time- cost-effectiveness based on green metrics.

Language: Английский

Annulation Cascades of Cyclosulfonium Salts and Alkenes towards Sulfur‐Containing N‐Heterocycles by Visible Light/Copper Catalysis DOI
Jie Ma, Xufeng Li, Yuqing Chen

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(14), P. 1637 - 1643

Published: April 3, 2024

Comprehensive Summary Although, great achievements have been made in the synthesis of heterocycles using radical addition/cyclization strategy, developing versatile alkyl precursors, especially non‐stabilized long chain radicals for this strategy still remains a huge challenge. Herein, we report an efficient annulation cascade reaction between cyclosulfonium salts and alkenes sulfur‐containing N ‐heterocycles by visible light/copper catalysis under mild conditions. The C—S bond cleavage/radical delivers variety corresponding containing aryl thioether motifs with good functional group tolerance. Significantly, current system could be used late‐stage functionalization complex bioactive molecules.

Language: Английский

Citations

4

TEMPO/PhI(OAc)2 promotes the α-aminophosphinoylation of alcohols with amines and H-phosphine oxides in aqueous medium DOI

Qiang Huang,

Xin Jin,

Lvjia Wu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(19), P. 3860 - 3865

Published: Jan. 1, 2024

The aminophosphinoylation of alcohols with amines and H-phosphine oxides provides an efficient mild approach to access various α-aminoalkylphosphine in good yields tolerance functional groups using H 2 O as a clean solvent.

Language: Английский

Citations

4

Copper-Catalyzed One-Pot Synthesis of Thiazolidin-2-imines DOI Creative Commons
Leandros P. Zorba,

Ioannis Stylianakis,

Nikolaos Tsoureas

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7727 - 7740

Published: May 10, 2024

The synthesis of thiazolines, thiazolidines, and thiazolidinones has been extensively studied, due to their biological activity related neurodegenerative diseases, such as Parkinson's Alzheimer's, well antiparasitic antihypertensive properties. closely thiazolidin-2-imines have studied less, efficient strategies for synthesizing them, mainly based on the reaction propargylamines with isothiocyanates, explored less. use one-pot approaches, providing modular, straightforward, sustainable access these compounds, also received very little attention. Herein, we report a novel, one-pot, multicomponent, copper-catalyzed among primary amines, ketones, terminal alkynes, toward bearing quaternary carbon centers five-membered ring, in good excellent yields. Density functional theory calculations, combined experimental mechanistic findings, suggest that copper(I)-catalyzed between situ-formed isothiocyanates proceeds lower energy barrier pathway leading S-cyclized product, compared N-cyclized one, chemo- regioselective formation 5-exo-dig thiazolidin-2-imines.

Language: Английский

Citations

4

Iodine(III)-Mediated Trifluoroacetylation of a C(sp2)–H or C(sp)–H Bond with Masked Trifluoroacyl Reagents DOI

Zhipeng Ye,

Meng Guo,

Yong-Qing Ye

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5196 - 5201

Published: June 10, 2024

A novel strategy for incorporating a trifluoroacetyl functionality into range of structurally varied unsaturated bonds was developed by using PhI(OCOMe)2 as an oxidant with masked trifluoroacyl reagent radical precursor. The oxidative decarboxylation the precursor followed tandem process provides versatile access to 5-exo-trig cyclization N-arylacrylamides, direct C(sp2)–H trifluoroacetylation quinolines, isoquinoline, 2H-indazole, and quinoxalin-2(1H)-ones, C(sp)–H alkynes. This protocol is characterized mild reaction conditions, operational simplicity, broad functional group compatibility.

Language: Английский

Citations

4

One-pot three-component synthesis of azaspirononatriene derivatives DOI Creative Commons

Ali Oudi,

Abbas Ali Esmaeili, Azizollah Habibi

et al.

Scientific Reports, Journal Year: 2025, Volume and Issue: 15(1)

Published: April 30, 2025

The present investigation has introduced a new class of isocyanide/acetylene-based multicomponent reactions (IAMCRs). These are robust technique for efficiently synthesizing intricate spiro architectures through zwitterionic adduct. coupling reaction between the "in situ" generated dipoles isocyanide-acetylenic ester adducts and 3-alkyl-4-arylidene-isoxazol-5(4H)-one derivative presents highly effective synthetic pathway obtaining novel 1-oxo-2-oxa-3-azaspiro[4.4]nona-3,6,8-triene heterocycles. broad range substrates, standard experimental conditions, straightforward procedure, impressive yields make our catalyst-free three-component approach practical green, as it remarkably offers step-, time- cost-effectiveness based on green metrics.

Language: Английский

Citations

0