ChemInform Abstract: 1,3-Dipolar Cycloadditions. Part 21. Catalytic Effects of Lewis Acids on 1,3-Dipolar Cycloaddition of C-(4-Chlorophenyl)-N-phenyl Nitrone to Benzylidene Acetophenone.

ChemInform ◽  
2011 ◽  
Vol 42 (40) ◽  
pp. no-no
Author(s):  
Nivedita Acharjee ◽  
Avijit Banerji ◽  
Thierry Prange
Keyword(s):  
Lewis Acids ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Catalytic Effects

Efficient Catalytic Effects of Lewis Acids in the 1,3-Dipolar Cycloaddition Reactions of Carbonyl Ylides with Imines

2005 ◽  
Vol 70 (26) ◽  
pp. 10782-10791 ◽  
Author(s):  
Hiroyuki Suga ◽  
Yasutaka Ebiura ◽  
Kazuaki Fukushima ◽  
Akikazu Kakehi ◽  
Toshihide Baba
Keyword(s):  
Lewis Acids ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Catalytic Effects

scholarly journals Efficient Catalytic Effects of Lewis Acids in the 1,3-Dipolar Cycloaddition Reactions of Carbonyl Ylides with Imines.

ChemInform ◽  
2006 ◽  
Vol 37 (19) ◽  
Author(s):  
Hiroyuki Suga ◽  
Yasutaka Ebiura ◽  
Kazuaki Fukushima ◽  
Akikazu Kakehi ◽  
Toshihide Baba
Keyword(s):  
Lewis Acids ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Catalytic Effects

scholarly journals Asymmetric Lewis acid-catalyzed 1,3-dipolar cycloadditions

2008 ◽  
Vol 80 (5) ◽  
pp. 1013-1018 ◽  
Author(s):  
Andrei Bădoiu ◽  
Yasmin Brinkmann ◽  
Florian Viton ◽  
E. Peter Kündig
Keyword(s):  
Transition Metal ◽  
Lewis Acid ◽  
Lewis Acids ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Asymmetric Catalytic ◽  
Aldehydes And Ketones ◽  
Acid Catalyzed

Highly tuned, one-point binding chiral iron and ruthenium complexes selectively coordinate and activate α,β-unsaturated aldehydes and ketones toward asymmetric catalytic Diels-Alder cycloaddition reactions. Here we focus on the application of these transition-metal Lewis acids to asymmetric catalytic 1,3-dipolar cycloaddition reaction between enals and cyclic and acyclic nitrones as well as aryl nitrile oxides to give isoxazolidines and isoxazolines, respectively.

1,3-Dipolar cycloadditions of Arylcarbonitrile Oxides and Diaryl Nitrilimines with Some 2-Arylmethylene-1,3-Indanediones; regiochemistry of the Reactions

2003 ◽  
Vol 2003 (4) ◽  
pp. 204-207 ◽  
Author(s):  
Sarra Boudriga ◽  
Mohiedinne Askri ◽  
Rafik Gharbi ◽  
Mohamed Rammah ◽  
Kabula Ciamala
Keyword(s):  
Ring Closure ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions

Ring-closure reaction affording spiroisoxazolines and spiropyrazolines via a 1,3-dipolar cycloaddition between the title compounds, occurs with high regioselectivity.

Regioselection in 1,3-Dipolar Cycloadditions of 3-Methylpyridine N-Imide to Aromatic Carbonitriles. Synthesis of 2-Aryl-8-Methyl[1,2,4]Triazolo [1,5-a]Pyridines

2002 ◽  
Vol 2002 (11) ◽  
pp. 560-561 ◽  
Author(s):  
Zhang Guolin ◽  
Hu Yongzhou
Keyword(s):  
Potassium Hydroxide ◽  
Dipolar Cycloaddition ◽  
Aromatic Nitriles ◽  
Dipolar Cycloadditions

1-Amino-3-methylpyridinium mesitylenesulfonate (3) reacts with aromatic nitriles in the presence of potassium hydroxide, undergoing 1,3-dipolar cycloaddition followed by elimination of H2 to give 2-aryl-8-methyl[1,2,4]triazolo[1,5- a]pyridines as the major products, rather than the 6-methyl isomers.

The 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides in Water Media

2021 ◽  
Vol 25 ◽  
Author(s):  
Joaquín Plumet
Keyword(s):  
Carbonyl Compounds ◽  
Critical Discussion ◽  
Aldol Reactions ◽  
Dipolar Cycloaddition ◽  
Hydroxy Ketone ◽  
Unsaturated Ketones ◽  
Dipolar Cycloadditions ◽  
Nitrile Oxides ◽  
Water Media ◽  
Synthetic Intermediates

: The 1,3-dipolar cycloadditions (DCs) of nitrile oxides (NOs) have been used as a powerful tool in synthetic organic chemistry. The cycloadducts arising from cycloadditions (CAs) of NOs to alkenes and alkynes (2-isoxazolines and isoxazoles respectively) are valuable synthetic intermediates because, among others, their capacity to mask other functionalities including α, β-unsaturated ketones, β-hydroxy carbonyl compounds and 1,3-aminoalcohols. In particular, the β-hydroxy ketone functionality is an illustrative example, making the NOs alkenes CAs reactions a synthetically equivalent methodology of aldol reactions. The vast majority of these reactions are carried out in organic solvents. Nevertheless, the use of water as an alternative solvent has evident advantages on the “Green Chemistry” concept. The critical discussion on the use of water instead of “conventional” solvents in the 1,3-DCs reactions of NOs is the objective of the present review.

scholarly journals Dipolar cycloadditions of HMF-based nitrones: stepwise and multicomponent reactions, stereochemical outcome and structural scope

2020 ◽  
Vol 22 (22) ◽  
pp. 7907-7912
Author(s):  
Lianjie Wang ◽  
Charlie Verrier ◽  
Mohammed Ahmar ◽  
Yves Queneau
Keyword(s):  
Multicomponent Reactions ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions

The straightforward preparation of new 3-furanyl isoxazolidines by 1,3-dipolar cycloaddition of 5-hydroxymetylfurfural (HMF)-derived nitrones with electro-deficient olefins is investigated.

1,3-Dipolar Cycloadditions of a Chiral Oxazolidinone With Nitrones and Nitrile Oxides

1995 ◽  
Vol 48 (9) ◽  
pp. 1511 ◽  
Author(s):  
SG Pyne ◽  
J Safaei-G ◽  
BW Skelton ◽  
AH White
Keyword(s):  
Single Crystal ◽  
Hydrogen Atmosphere ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
The Novel ◽  
X Ray ◽  
Dipolar Cycloadditions ◽  
Nitrile Oxides ◽  
Exocyclic Methylene

The 1,3-dipolar cycloaddition reactions of the chiral oxazolidinone (1) and nitrones are highly regioselective and only 5,5-disubstituted isoxazolidine adducts are formed. These reactions occur under equilibrating conditions to give the more stable adducts that result from addition to the exocyclic methylene of (1) from the sterically more hindered π-face. The endo adducts are generally thermodynamically favoured. In one case the novel azetidine (21) was formed from the treatment of the adduct (4a) with palladium hydroxide on carbon under a hydrogen atmosphere. The major adducts from the reaction of (1) and nitrile oxides (16a,b) had the expected stereochemistry, addition of the 1,3-dipole having occurred from the less hindered π-face of the exocyclic methylene of (1). The stereochemistry of many of these products has been elucidated by single-crystal X-ray structural determinations.

Improved Protocols for Microwave-Assisted Cu(I)-Catalyzed Huisgen 1,3-Dipolar Cycloadditions

2007 ◽  
Vol 72 (8) ◽  
pp. 1014-1024 ◽  
Author(s):  
Pedro Cintas ◽  
Katia Martina ◽  
Bruna Robaldo ◽  
Davide Garella ◽  
Luisa Boffa ◽  
...  
Keyword(s):  
Heterogeneous Catalysis ◽  
Microwave Irradiation ◽  
Ultrasound Irradiation ◽  
Conventional Heating ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Click Reactions ◽  
Dipolar Cycloadditions ◽  
Microwave Assisted ◽  
New Applications

The Huisgen 1,3-dipolar cycloaddition of azides and acetylenes catalyzed by Cu(I) salts, leading to 1,2,3-triazoles, is one of the most versatile "click reactions". We have developed a series of optimized protocols and new applications of this reaction starting from several substrates, comparing heterogeneous vs homogeneous catalysis, conventional heating vs microwave irradiation or simultaneous microwave/ultrasound irradiation. Both non-conventional techniques strongly promoted the cycloaddition (bromide → azide → triazole), that could be conveniently performed in a one-pot procedure. This was feasible even with such bulky molecules as functionalized β-cyclodextrins (β-CD), starting from 61-O-tosyl-β-CD or from heptakis[6-O-(tert-butyldimethylsilyl)]-21-O-propargyl-β-CD. "Greener" heterogeneous catalysis with charcoal-supported Cu(II) or Cu(I) (prepared under ultrasound) was advantageously employed.

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