scholarly journals Cu/TEMPO catalyzed dehydrogenative 1,3-dipolar cycloaddition in the synthesis of spirooxindoles as potential antidiabetic agents

RSC Advances ◽  
2020 ◽  
Vol 10 (21) ◽  
pp. 12262-12271 ◽  
Author(s):  
Chitrala Teja ◽  
Spoorthy N. Babu ◽  
Ayesha Noor ◽  
J. Arul Daniel ◽  
S. Asha Devi ◽  
...  
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Antidiabetic Agents ◽  
Decarboxylative Condensation

A series of spiro-[indoline-3,3′-pyrrolizin/pyrrolidin]-2-ones were synthesized from Cu–TEMPO catalyzed dehydrogenation followed by 1,3-dipolar cycloaddition of azomethine ylides via decarboxylative condensation, resulting in high regioselectivities and yields.

scholarly journals Synthesis of polysubstituted spiropyrrolidines using 2-acetylfuran, 2-acetylthiophene, and 2-acetylpyrrole

2021 ◽  
Vol 21 (3) ◽  
pp. 254-259
Author(s):  
Svetlana V. Borisova ◽  
◽  
Vitaly V. Sorokin ◽  
Keyword(s):  
13C Nmr Spectroscopy ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Knoevenagel Reaction ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Stereo Selectivity ◽  
Decarboxylative Condensation ◽  
First Time

A series of novel spirooxindoles have been synthesized through three-component 1,3-dipolar cycloaddition of azomethine ylides generated in situ by the decarboxylative condensation of isatin and sarcosine with the dipolarophile 3-phenyl-1-(heteroaryl -2-yl)prop-2-en-1- one, synthesized by the Knoevenagel reaction using 2-acetylfuran, 2-acetylpyrrole, 2-acetylthiophene and substituted benzaldehydes. These compounds are used for the first time as dipolarophiles. This method has the advantages of mild reaction conditions, high atom economy, excellent yields, and high regio- and stereo-selectivity. The reaction was carried out by mixing equimolar amounts of enone and isatin, as well as a slight excess of sarcosine in isopropyl alcohol when heated to 60–70°C. Among the enones with various heterocyclic substituents, it is most convenient to use compounds containing a pyrrole fragment as dipolarophiles, since the products are obtained in a short amount of time in good yields. The use of enones obtained from 2-acetylthiophene leads to an increase in the reaction time, and from 2-acetylfuran - to a significant resinification of the reaction mixture. The structures of the compounds obtained were proved using a combination of 1H, 13C NMR spectroscopy data, as well as two-dimensional NMR experiments of heteronuclear correlation, HSQC and HMBC. Based on the data obtained, a mechanism for the formation of products has been proposed.

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.

ChemInform Abstract: Oligopyrrole Synthesis by 1,3-Dipolar Cycloaddition of Azomethine Ylides with Bissulfonyl Ethylenes.

ChemInform ◽  
2008 ◽  
Vol 39 (15) ◽  
Author(s):  
Ana Lopez-Perez ◽  
Rocio Robles-Machin ◽  
Javier Adrio ◽  
Juan Carlos Carretero
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition

scholarly journals Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides

2016 ◽  
Vol 22 (14) ◽  
pp. 4952-4959 ◽  
Author(s):  
Alberto Ponce ◽  
Inés Alonso ◽  
Javier Adrio ◽  
Juan C. Carretero
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition

Ligand-controlled stereodivergent 1,3-dipolar cycloaddition of azomethine ylides with 3-methyl-4-nitro-5-styrylisoxazoles

2016 ◽  
Vol 52 (60) ◽  
pp. 9458-9461 ◽  
Author(s):  
Kang Liu ◽  
Yong Xiong ◽  
Zuo-Fei Wang ◽  
Hai-Yan Tao ◽  
Chun-Jiang Wang
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition

An unprecedented Ag(i)-catalyzed ligand-controlled stereodivergent 1,3-dipolar cycloaddition of azomethine ylides with 3-methyl-4-nitro-5-styrylisoxazoles has been developed to afford heterocycles bearing both methylisoxazole and pyrrolidine moieties.

Intramolecular 1,3-Dipolar Cycloaddition of Geminal Difluoro Azomethine Ylides at Multiple Carbon—Carbon Bonds.

ChemInform ◽  
2005 ◽  
Vol 36 (45) ◽  
Author(s):  
M. S. Novikov ◽  
A. F. Khlebnikov ◽  
I. V. Voznyi ◽  
O. V. Besedina ◽  
R. R. Kostikov
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds

Bifunctional AgOAc/ThioClickFerrophos catalyzed asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides to nitroalkenes

Tetrahedron ◽  
2016 ◽  
Vol 72 (21) ◽  
pp. 2666-2670 ◽  
Author(s):  
Midori Kimura ◽  
Yukiko Matsuda ◽  
Akihiro Koizumi ◽  
Chihiro Tokumitsu ◽  
Yuichiro Tokoro ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition
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