scholarly journals Nonstabilized Azomethine Ylides Generated by Decarboxylative Condensation of α-Amino Acids. Structural Variation, Reactivity, and Stereoselectivity

1989 ◽  
Vol 62 (6) ◽  
pp. 1960-1968 ◽  
Author(s):  
Shuji Kanemasa ◽  
Kazushige Sakamoto ◽  
Otohiko Tsuge
Keyword(s):  
Amino Acids ◽  
Structural Variation ◽  
Azomethine Ylides ◽  
Decarboxylative Condensation

ChemInform Abstract: Azomethine Ylides from the Reaction of 4-(Dicyanomethylene)-3-methyl-1- phenyl-2-pyrazoline-5-one with α-Amino Acids and Their Esters.

ChemInform ◽  
2010 ◽  
Vol 22 (32) ◽  
pp. no-no
Author(s):  
S. A. M. METWALLY ◽  
M. F. ALY ◽  
M. A. ABD-ALLA ◽  
F. M. ATTA ◽  
M. E. ABD-EL-MONEM
Keyword(s):  
Amino Acids ◽  
Azomethine Ylides

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.

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.

Asymmetric Cycloaddition ofN-Metalated Azomethine Ylides with the Optically Active α,β-Unsaturated Esters Derived from α-Amino Acids

1990 ◽  
Vol 63 (10) ◽  
pp. 2857-2865 ◽  
Author(s):  
Shuji Kanemasa ◽  
Hidetoshi Yamamoto ◽  
Eiji Wada ◽  
Tosio Sakurai ◽  
Kunio Urushido
Keyword(s):  
Amino Acids ◽  
Optically Active ◽  
Azomethine Ylides ◽  
Unsaturated Esters

1,3-Dipolar Cycloadditions to Unsymmetrical Ketone-Derived Chiral Stabilized Azomethine Ylides: Strategies for the Synthesis of Highly Substituted Amino Acids

Synthesis ◽  
2005 ◽  
pp. 3271-3278 ◽  
Author(s):  
Laurence M. Harwood ◽  
David J. Aldous ◽  
Michael G. Drew ◽  
William N. Draffin ◽  
Estelle M-N. Hamelin ◽  
...  
Keyword(s):  
Amino Acids ◽  
Azomethine Ylides ◽  
Dipolar Cycloadditions ◽  
Stabilized Azomethine Ylides
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