Green Protocols in Heterocycle Syntheses via 1,3-Dipolar Cycloadditions

Martina, Katia; Tagliapietra, Silvia; Veselov, Valery V.; Cravotto, Giancarlo

doi:10.3389/fchem.2019.00095

Cited by 65 publications

(35 citation statements)

References 57 publications

(57 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The pair of diastereomer 5c were separated using the HPLC technique qualitatively. The mechanism of epoxidation includes a concerted reaction mechanism characterized by a four‐part, cyclic transition state, as a result, the electropositive, oxygen atom ended up in the cyclopropane ring, and the COO 2 H group becomes COOH . MMPP has electropositive oxygen atom on carboxylic group.…”

Section: Resultsmentioning

confidence: 99%

Green synthetic investigation and spectral characterization of some spiro pyrazolidine‐based heterocycles with potential biological activity

El‐Ossaily

Metwally

Al‐Muailkel

et al. 2020

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

A green, rapid, and efficient methodology is developed for the synthesis of 1‐phenyl‐3,5‐pyrazolidinedione (3) by the reaction of malonic acid with phenyl hydrazine in the presence of phosphorous oxychloride under solvent‐free conditions. The later compound 3 was used as a versatile precursor for green synthesis of chalcone derivatives (4a‐h) and spiroheterocyclic compounds (5a‐h) with good to excellent isolated yields. The chemical structures of the synthesized compounds were elucidated on the basis of elemental and spectral analyses.

show abstract

Section: Resultsmentioning

confidence: 99%

Green synthetic investigation and spectral characterization of some spiro pyrazolidine‐based heterocycles with potential biological activity

El‐Ossaily

Metwally

Al‐Muailkel

et al. 2020

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…Some studies of pericyclic cycloadditions showed great benefits when insoluble reagents were suspended in water, explicating this effect due to a reaction rate acceleration for the "on water" conditions [65]. In particular, comparative studies of 1,3-dipolar cycloadditions in organic solvents with water as a co-solvent or only in pure water showed a remarkable rate acceleration increase, probably due to hydrophobic effects with organic reagents, a lowering of activation energy by hydrogen bonds in the transition state, and an increased solvation stabilization [66].…”

Section: 3-dc In Watermentioning

confidence: 99%

Recent Developments on 1,3-Dipolar Cycloaddition Reactions by Catalysis in Green Solvents

et al. 2020

View full text Add to dashboard Cite

The use of eco-compatible synthetic procedures in organic reactions and, in particular, in 1,3-dipolar cycloaddition reactions, has recently received a great deal of attention and considerable progress has been achieved in this area in the last years. This review summarizes the approaches currently employed to synthesize heterocyclic compounds by catalyzed 1,3-dipolar cycloadditions in green solvents in the last six years. Our choice to do a selection of the literature from 2014 to 2019 was made considering the absence of a recent review about this period, to our knowledge. Several examples to construct heterocycles by 1,3-dipolar cycloadditions will be discussed in this work subdivided in function of the most important class of non-conventional and green solvents, i.e., ionic liquids (ILs), deep eutectic solvents (DES), and water.

show abstract

“…The objective of this report is the consideration of the use of some of these “unconventional” techniques in the 1.3‐DCs of NOs, giving coverage on the more significant progress made on the topic especially during the last ten years until February 2020. The following subjects have been considered: (a) the use of ILs and scCO 2 as alternative solvents in 1,3 DCs of NOs; (b) MW and US activation in NOs CAs; (c) NOs CAs under continuous flow …”

Section: Introduction and Objectivesmentioning

confidence: 99%

1,3‐Dipolar Cycloaddition Reactions of Nitrile Oxides under “Non‐Conventional” Conditions: Green Solvents, Irradiation, and Continuous Flow

Plumet

2020

ChemPlusChem

View full text Add to dashboard Cite

The 1,3‐dipolar cycloaddition reactions (DCs) of nitrile oxides (NOs) to alkenes and alkynes are useful methods for the synthesis of 2‐isoxazolines and isoxazoles respectively, which are important classes of heterocyclic compounds in organic and medicinal chemistry. Most of these reactions are carried out in organic solvents and under thermal activation. Nevertheless the use of supercritical carbon dioxide (scCO2) and ionic liquids (Ils) as alternative solvents and the application of microwave (MW) and ultrasound (US) as alternative activation procedures have evident advantages from the “Green Chemistry” point of view. The critical discussion on the applications of these “unconventional” activation methods and reaction conditions in the 1,3‐DCs of NOs is the objective of the present Review.

show abstract

Green Protocols in Heterocycle Syntheses via 1,3-Dipolar Cycloadditions

Cited by 65 publications

References 57 publications

Green synthetic investigation and spectral characterization of some spiro pyrazolidine‐based heterocycles with potential biological activity

Green synthetic investigation and spectral characterization of some spiro pyrazolidine‐based heterocycles with potential biological activity

Recent Developments on 1,3-Dipolar Cycloaddition Reactions by Catalysis in Green Solvents

1,3‐Dipolar Cycloaddition Reactions of Nitrile Oxides under “Non‐Conventional” Conditions: Green Solvents, Irradiation, and Continuous Flow

Contact Info

Product

Resources

About