scholarly journals Additive-assisted regioselective 1,3-dipolar cycloaddition of azomethine ylides with benzylideneacetone

2014 ◽  
Vol 10 ◽  
pp. 352-360 ◽  
Author(s):  
Chuqin Peng ◽  
Jiwei Ren ◽  
Jun-An Xiao ◽  
Honggang Zhang ◽  
Hua Yang ◽  
...  
Keyword(s):  
Substituent Effects ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Nitrobenzoic Acid

1,3-Dipolar cycloadditions of isatins, benzylamine and benzylideneacetones were studied to prepare a series of novel spiropyrrolidine-oxindoles – 4′-acetyl-3′,5′-diarylspiro[indoline-3,2′-pyrrolidin]-2-ones and 3′-acetyl-4′,5′-diarylspiro[indoline-3,2′-pyrrolidine]-2-ones in good yields of up to 94% and with good regioselectivities. Regioselectivities are reversible by the addition of water or 4-nitrobenzoic acid, respectively. The substituent effects on the regioselectivity were also investigated.

scholarly journals Multilayer graphene functionalized through thermal 1,3-dipolar cycloadditions with imino esters: a versatile platform for supported ligands in catalysis

2019 ◽  
Vol 55 (52) ◽  
pp. 7462-7465 ◽  
Author(s):  
Marcos Ferrándiz-Saperas ◽  
Alessio Ghisolfi ◽  
Diego Cazorla-Amorós ◽  
Carmen Nájera ◽  
José M. Sansano
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Multilayer Graphene ◽  
Dipolar Cycloadditions ◽  
Chelating Ligand ◽  
Imino Esters

Multilayer graphene (MLG), obtained by mild sonication of graphite, was functionalized via 1,3-dipolar cycloaddition with azomethine ylides and used as a heterogeneous N,O-chelating ligand to coordinate iridium atomic centers.

Diastereoselective 1,3-Dipolar Cycloadditions and Michael Reactions of Azomethine Ylides to (2R)-3-Benzoyl-4-methylidene-2-phenyloxazolidin-5-one and (2S)-3-Benzoyl-2-t-butyl-4-methylideneoxazolidin-5-one

1998 ◽  
Vol 51 (2) ◽  
pp. 137 ◽  
Author(s):  
Stephen G. Pyne ◽  
Javad Safaei-G. ◽  
Karl Schafer ◽  
Abdollah Javidan ◽  
Brian W. Skelton ◽  
...  
Keyword(s):  
Amino Acid ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Amino Acid Esters ◽  
Dipolar Cycloadditions ◽  
Michael Reactions ◽  
Michael Adducts ◽  
Practical Synthesis ◽  
The Michael Addition ◽  
Acid Esters

The 1,3-dipolar cycloaddition reactions of (1) and (11) with the azomethine ylides derived from N-benzylidene α-amino acid esters (2) proceed with good to high exo-diastereoselectivity giving the cycloadducts (4) and (12), respectively. The cycloaddition adducts can be converted to highly functionalised prolines (14), (15) and (17) in high enantiomeric purities. The Michael addition adducts of (1) and (11) with the azomethine ylides derived from the N-(disubstituted methylidene) α-amino acid esters (18), (19) and (33) allow for a practical synthesis of all four stereoisomers of 4-benzamidopyroglutamate. The stereochemistry of these cycloaddition and Michael adducts has been extensively determined by single-crystal X-ray structural analysis [compounds (4b), (5b,d), (12b,d), (13e), (15), (20), (21) and (27)]. Lithium-chelated transition state structures have been proposed to rationalize the stereochemical outcomes of these reactions.

scholarly journals Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

2019 ◽  
Vol 91 (4) ◽  
pp. 575-596 ◽  
Author(s):  
Carmen Nájera ◽  
José Miguel Sansano
Keyword(s):  
Amino Acid ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Amino Acid Derivatives ◽  
Reaction Conditions ◽  
Dipolar Cycloadditions ◽  
Spiro Derivatives ◽  
Stabilized Azomethine Ylides

Abstract Different multicomponent 1,3-dipolar cycloadditions (1,3-DC) of cyclic α-amino acid derivatives with aldehydes and dipolarophiles have been described as efficient and simple methodologies for the synthesis of the pyrrolidine unit of pyrrolizidines and indolizidines. When free cyclic α-amino acids are used, a thermal promoted decarboxylative process generates in situ the corresponding non-stabilized azomethine ylides, which afforded the corresponding pyrrolizidines and indolizidines with a hydrogen in the bicyclic units. This methodology has been employed to the synthesis of complex systems including spiro derivatives when ketones are used as carbonyl component. In addition, working with cyclic α-amino acid derived esters, the three-component 1,3-DC takes place under milder reaction conditions giving the corresponding pyrrolizidines and indolizidines with an alkoxycarbonyl group in the bridge adjacent carbon to the nitrogen. This methodology can be carried out by a double consecutive or stepwise 1,3-DC to provide pyrrolizidines via the precursor prolinates. The conformation of the azomethine ylide controls the endo/exo diastereoselectivity of the 1,3-DC.

Phenanthridinium-Based Azomethine Ylides in 1,3-Dipolar Cycloaddition with Dimethyl Acetylenedicarboxylate

1994 ◽  
Vol 59 (12) ◽  
pp. 2641-2649 ◽  
Author(s):  
Milan Potáček ◽  
Tomáš Topinka ◽  
Jiří Dostál ◽  
Jaromír Marek
Keyword(s):  
Dimethyl Fumarate ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray ◽  
Dipolar Cycloadditions ◽  
Unstable Species

Azomethine ylides generated from 5-(alkoxycarbonylmethyl) phenanthridinium cations I were used in the 1,3-dipolar cycloadditions with dimethyl acetylenedicarboxylate as dipolarophile. The cycloadducts II were found to be very unstable species and readily oxidized to fully aromatic pyrrolo[1,2-f]phenanthridines III. Their structure was compared with the compounds formed by the oxidation of cycloadducts IV of the same ylide with dimethyl fumarate and maleate. In both cases pyrrolines V were found as intermediates. The structure of the products was determined by NMR and MS as well as by X-ray analysis.

Enantioselective synthesis of 8-azabicyclo[3.2.1]octanes via asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual catalytic system

2019 ◽  
Vol 55 (11) ◽  
pp. 1552-1555 ◽  
Author(s):  
Hiroyuki Suga ◽  
Masahiro Yoshiwara ◽  
Takaaki Yamaguchi ◽  
Takashi Bando ◽  
Mizuki Taguchi ◽  
...  
Keyword(s):  
Catalytic System ◽  
Enantioselective Synthesis ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
System P

The asymmetric 1,3-dipolar cycloaddition between diazo imine-derived cyclic azomethine ylides and acryloylpyrazolidinone using a dual catalytic system is reported.

scholarly journals Current Trends towards the Synthesis of Bioactive Heterocycles and Natural Products Using 1,3-Dipolar Cycloadditions (1,3-DC) with Azomethine Ylides

Synthesis ◽  
2017 ◽  
Vol 49 (13) ◽  
pp. 2819-2851 ◽  
Author(s):  
H. Döndas ◽  
María de Gracia Retamosa ◽  
José Sansano
Keyword(s):  
Natural Products ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Current Trends ◽  
Bioactive Heterocycles ◽  
Asymmetric Cycloadditions

This review summarizes the trends in the formation of complex or not so complex heterocyclic structures through 1,3-dipolar cy­cloadditions of azomethine ylides. Diastereo- and enantioselective processes as well as non-asymmetric cycloadditions constitute very important synthetic tools for achieving these compounds. This review covers the literature from 2015 through 2016 and organizes the research in terms of biologically important heterocycles and natural products from cascade 1,3-dipolar cycloadditions of azomethine ylides to the simpler forms of 1,3-dipolar cycloaddition.1 Introduction2 Synthesis of Spirooxindoles3 Synthesis of Spiropyrrolidines4 Synthesis of Spiropiperidines and Piperidines5 Synthesis of Pyrrolidines and Fused Pyrrolidines6 Synthesis of Pyrrolizidines and Indolizidines7 Synthesis of Quinolone and Isoquinolines8 Conclusions

Reactions of 4-Pyrones with Azomethine Ylides as a Chemo­selective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines

Synthesis ◽  
2021 ◽  
Author(s):  
Dmitrii L. Obydennov ◽  
Vyacheslav D. Steben’kov ◽  
Konstantin L. Obydennov ◽  
Sergey A. Usachev ◽  
Vladimir S. Moshkin ◽  
...  
Keyword(s):  
Double Bond ◽  
Ring Opening ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Computational Studies ◽  
Carbon Double Bond ◽  
Reactivity Indexes ◽  
Reaction Proceeds

Abstract4-Pyrones bearing electron-donating and electron-withdrawing groups react with nonstabilized azomethine ylides to form pyrano[2,3-c]pyrrolidines in moderate to good yields. The reaction proceeds chemoselectively as a 1,3-dipolar cycloaddition of the azomethine ylide at the carbon–carbon double bond of the pyrone activated by the electron-withdrawing substituent. The reactivity of 4-pyrones toward azomethine ylides was rationalized by computational studies with the use of reactivity indexes. The pyrano[2,3-c]pyrrolidine moiety could be modified, for example by a ring-opening transformation under the action of hydrazine to provide pyrazolyl-substituted pyrrolidines.

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.

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