Stereoselective Syntheses of Masked β‐Amino Acid Containing Phthalides DOI Creative Commons

Lorenzo Serusi,

Paul Zebrowski, Johannes Schörgenhumer

et al.

Helvetica Chimica Acta, Journal Year: 2022, Volume and Issue: 105(11)

Published: Sept. 20, 2022

We herein report a protocol for the asymmetric aldol-initiated cascade addition of isoxazolidin-5-ones to ortho-cyanobenzaldehydes by using Takemoto's bifunctional organocatalyst. This approach allows synthesis various novel β2,2-amino acid-phthalide conjugates with good enantio- and diastereoselectivities in reasonable yields further ring-opening these compounds acyclic carboxylic acid derivatives was demonstrated too.

Language: Английский

Oxazole and isoxazole: From one-pot synthesis to medical applications DOI

Ajay Thakur,

Monika Verma, Ruchi Bharti

et al.

Tetrahedron, Journal Year: 2022, Volume and Issue: 119, P. 132813 - 132813

Published: May 28, 2022

Language: Английский

Citations

51
Green and clean synthesis of 4-arylideneisoxazol-5-ones using NaCl aqueous solution DOI Creative Commons

Faezeh Haidary,

Hamzeh Kiyani

Sustainable Chemistry for the Environment, Journal Year: 2024, Volume and Issue: 5, P. 100066 - 100066

Published: Jan. 6, 2024

The one-pot, three-component cyclization reaction a wide variety of aryl/heteroaryl aldehydes, hydroxylamine hydrochloride, and β-keto ester compounds was performed in simple manner. reactions carried out the presence sodium chloride (NaCl) as profitable, green, efficient catalyst at room temperature. Optimization experiments indicate that amount 17 mol% loaded NaCl is sufficient to catalyze reaction. Among advantages this NaCl-catalyzed method are availability catalyst, no need for synthesis several steps, commercially available reactants, use aqueous conditions, clean synthesis, non-inflammable medium, environmental pollution, safety, cost-effectiveness, pot-economy, optimum efficiency, carbon economy steps. Due absence harmful solvents, an abundant, low-cost, useful water solvent, considered green synthesis.

Language: Английский

Citations

6
Catalyst-Free Selective Synthesis of E-Tetrasubstituted Olefins via Tandem Reaction of 3-Acetyl-4-phenyl-1-oxaspiro[4.5]deca-3,6,9-triene-2,8-dione with Amine, C–C Bond Breakage, and Proton Transfer DOI
Tingting Zhang, Xinkun An,

Guoen Cui

et al.

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

Published: Feb. 25, 2025

The Z- or E-selective syntheses of tetrasubstituted olefins present big challenges. Tremendous efforts are ongoing to overcome this issue, especially for acyclic structures. In work, an E-stereoselective synthetic method through tandem reaction 1,4-Michael addition 3-acetyl-4-phenyl-1-oxaspiro[4.5]deca-3,6,9-triene-2,8-dione with amine, C-C bond breakage, and proton transfer by intermolecular hydrogen bonds was revealed excellent atom economy without catalysts additives. A diverse set E-tetrasubstituted were obtained in 43% 93% yields functional group tolerance late-stage modifications complex drug molecules. mechanism proposed based on the deuterium-labeling experiment density theory (DFT) calculation.

Language: Английский

Citations

0
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
Rh(III)-Catalyzed Regioselective Annulations of 3-Arylisoxazolones and 3-Aryl-1,4,2-dioxazol-5-ones with Propargyl Alcohols: Access to 4-Arylisoquinolines and 4-Arylisoquinolones DOI
Tongtong Wang, Hai‐Shan Jin,

Manman Cao

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(15), P. 5952 - 5957

Published: July 29, 2021

The Rh(III)-catalyzed dual directing group assisted C–H activation/annulation of 3-arylisoxazolones with propargyl alcohols has been developed, which expands the application scope isoxazolones in organic synthesis. This protocol also worked well 3-aryl-1,4,2-dioxazol-5-ones to produce synthetically and biologically important 4-arylisoquinolones.

Language: Английский

Citations

24
Steglich’s Base Catalyzed Three-Component Synthesis of Isoxazol-5-Ones DOI

Zeinab Faramarzi,

Hamzeh Kiyani

Polycyclic aromatic compounds, Journal Year: 2022, Volume and Issue: 43(4), P. 3099 - 3121

Published: April 7, 2022

4-(Dimethylamino)pyridine (DMAP) has been used as an efficient Brønsted organo-base catalyst for the one-pot, three-component cyclization of various aldehydes, β-keto esters, and hydroxylamine hydrochloride. In this organocatalyzed reaction, 3,4-disubstituted isoxazole-5(4H)-ones were efficiently formed in high yields relatively shorter reaction times. Using 8 mol% DMAP, a mixture water–ethanol solvent system, 80 °C gave best results. The heterocyclization using arylaldehydes containing electron releasing groups is well performed heterocyclic products obtained good to isolated yields. Aldehydes with withdrawing did not lead formation products. This method many advantages such broad substituent scope, mild eco‐friendly conditions, step atom economy, commercially available, inexpensive organo-basic catalyst.

Language: Английский

Citations

18
Rapid synthesis of fully substituted arylideneisoxazol-5(4H)-one using zinc oxide nanoparticles DOI

Shiva Aslanpour,

Hamzeh Kiyani

Research on Chemical Intermediates, Journal Year: 2023, Volume and Issue: 49(10), P. 4603 - 4619

Published: July 9, 2023

Language: Английский

Citations

10
Synthesis of Isoxazole-5(4 H )-ones Using Citrazinic Acid as an Organocatalyst in Aqueous Conditions DOI

Hanieh Ostadzadeh,

Hamzeh Kiyani

Organic Preparations and Procedures International, Journal Year: 2023, Volume and Issue: 55(6), P. 538 - 548

Published: March 24, 2023

Click to increase image sizeClick decrease size AcknowledgmentsThe authors thank the Damghan University Research Council. The corresponding author also thanks Shahrekord University.

Language: Английский

Citations

9
Access to β-Alkylated γ-Functionalized Ketones via Conjugate Additions to Arylideneisoxazol-5-ones and Mo(CO)6-Mediated Reductive Cascade Reactions DOI Creative Commons

Antonio Macchia,

Francesco F. Summa, Guglielmo Monaco

et al.

ACS Omega, Journal Year: 2022, Volume and Issue: 7(10), P. 8808 - 8818

Published: March 4, 2022

1,4-Conjugate addition of ((chloromethyl)sulfonyl)benzenes to arylideneisoxazol-5-ones, followed by one-pot, N-selective trapping in the presence electrophiles, was investigated. This strategy led synthesis new, stable N-protected isoxazol-5-ones good yields and high diastereolectivity. The study reactivity obtained products Mo(CO)6/H2O system allowed development a cascade reaction leading novel methyl ketones unchanged dr bearing an uncommon chloromethinearylsulfonyl end group.

Language: Английский

Citations

13
Arylideneisoxazole-5(4H)-One Synthesis by Organocatalytic Three-Component Hetero-Cyclization DOI

Ziba Daroughehzadeh,

Hamzeh Kiyani

Polycyclic aromatic compounds, Journal Year: 2023, Volume and Issue: 44(5), P. 3200 - 3221

Published: July 5, 2023

An expedient, green, practical, and vastly efficient three-component cyclo-condensation is catalyzed by triphenylphosphine. The 4-arylideneisoxazol-5(4H)-one heterocycles are generated in good to excellent isolated reaction yields. Experiments show that the best results were obtained using 15 mol% of catalyst under aqueous conditions at room temperature. sonochemical synthesis derivatives also performed 10 triphenylphosphine water as an eco-friendly medium. In comparative method, ultrasonication showed shorter times requires smaller amounts catalyst. While aryl/heteroaryl aldehydes used, variation β-keto-ester was explored. β-keto-esters (ethyl acetoacetate/ethyl 4-chloro-3-oxobutanoate/ethyl 3-oxohexanoate) optimized reacted well afforded corresponding 4-arylideneisoxazol-5(4H)-ones times. approach simple, approximately compatible with pot-, atom-, step-economy.

Language: Английский

Citations

7