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Journal Article•DOI•

1,3-Dipolar cycloadditions of nonstabilized azomethine ylides to planar chalcones via regio-and stereoselective route: A three-component strategy

Biswajit Gayen1, Avijit Banerji2, Kaliprasanna Dhara2•
Budge Budge Institute of Technology1, University of Calcutta2
11 Jan 2016-Synthetic Communications (Taylor & Francis)-Vol. 46, Iss: 4, pp 293-308
TL;DR: In this article, simple and efficient strategies toward the synthesis of trisubstituted pyrrolizidines and disubstitized oxazolidine systems by 1,3-dipolar cycloaddition reactions using arylaldehydes and α-amino acids have been developed, followed by a one-pot, three-component strategy.
About: This article is published in Synthetic Communications.The article was published on 2016-01-11 and is currently open access. It has received 12 citations till now. The article focuses on the topics: Azomethine ylide & Cycloaddition.

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Summary

  • Serial No. Content Page number 1 Materials and methods 2 2 Synthesis and characterization data of Substituted Pyrrolizidines compounds (8a-8j) 3-7 3 Synthesis and characterization data of Oxazolidines compounds (9a-9f) 8-9 4 NMR and IR spectra of the Compounds (8a, 9f) 10-14 5 Summary of crystal data 15-23 1.
  • Dimethylformamide (DMF) was dried and stored using molecular sieves.
  • Two sets of hydrogen-bonds originate from each carbonyl and direct orientation of packing of adjacent molecules in the crystal lattice.
  • The crystal of 9f presented a very interesting arrangement of eight molecules per unit cell.

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Citations
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Journal Article•DOI•
Current Trends towards the Synthesis of Bioactive Heterocycles and Natural Products Using 1,3-Dipolar Cycloadditions (1,3-DC) with Azomethine Ylides

[...]

H. Ali Dondas1, María de Gracia Retamosa2, José M. Sansano3•
Mersin University1, Spanish National Research Council2, University of Alicante3
07 Jun 2017-Synthesis
TL;DR: A review summarizes the trends in the formation of complex or not so complex heterocyclic structures through 1,3-dipolar cycloadditions of azomethine ylides as discussed by the authors.
Abstract: 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 Introduction 2 Synthesis of Spirooxindoles 3 Synthesis of Spiropyrrolidines 4 Synthesis of Spiropiperidines and Piperidines 5 Synthesis of Pyrrolidines and Fused Pyrrolidines 6 Synthesis of Pyrrolizidines and Indolizidines 7 Synthesis of Quinolone and Isoquinolines 8 Conclusions

114 citations

Journal Article•DOI•
Recent advances in the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and dipolarophiles

[...]

Bilel Bdiri1, Boa-Jing Zhao1, Zhiming Zhou1•
Beijing Institute of Technology1
15 Jul 2017-Tetrahedron-asymmetry
TL;DR: In this article, a detailed overview of the latest developments in this area since 2014 and highlight the recent improvements in the structural scope of dipolarophiles, azomethine ylide precursors, and chiral ligands.
Abstract: The synthesis of diastereo- and enantiopure heterocyclic molecules via catalytic asymmetric 1,3-dipolar cycloaddition reaction between azomethine ylides, generated in situ from α-amino acid-derived iminoesters and dipolarophiles is considered one of the most powerful and versatile techniques. In this review, we make a detailed overview of the latest developments in this area since 2014 and highlight the recent improvements in the structural scope of dipolarophiles, azomethine ylide precursors, and chiral ligands.

98 citations

Journal Article•DOI•
Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

[...]

Carmen Nájera1, José M. Sansano1•
University of Alicante1
24 Apr 2019-Pure and Applied Chemistry
TL;DR: The authors gratefully acknowledge financial support from the Spanish Ministerio de Economia y Competitividad (MINECO) (projects CTQ2013-43446-P and CTQ2014-51912-REDC) and the Generalitat Valenciana (PROMETEOII/2014/017), the University of Alicante and the Fondo Europeo de Desarrollo Regional (FEDER, EU).
Abstract: We gratefully acknowledge financial support from the Spanish Ministerio de Economia y Competitividad (MINECO) (projects CTQ2013-43446-P and CTQ2014-51912-REDC), the Spanish Ministerio de Economia, Industria y Competitividad, Agencia Estatal de Investigacion (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P and CTQ2016-81797-REDC), the Generalitat Valenciana (PROMETEOII/2014/017) and the University of Alicante.

26 citations

Journal Article•DOI•
The [4+2]-Cycloaddition of α-Nitrosoalkenes with Thiochalcones as a Prototype of Periselective Hetero-Diels-Alder Reactions-Experimental and Computational Studies.

[...]

Grzegorz Mlostoń, Katarzyna Urbaniak, Marcin Jasiński, Ernst-Ulrich Würthwein1, Heinz Heimgartner2, Reinhold Zimmer3, Hans-Ulrich Reissig3 •
University of Münster1, University of Zurich2, Free University of Berlin3
02 Jan 2020-Chemistry: A European Journal
TL;DR: A prototype of a highly periselective and regioselective cycloaddition has been identified and kinetically controlled processes confirming the role of thioketones as superdienophiles.
Abstract: The [4+2]-cycloadditions of alpha-nitrosoalkenes with thiochalcones occur with high selectivity at the thioketone moiety of the dienophile providing styryl-substituted 4H-1,5,2-oxathiazines in moderate to good yields. Of the eight conceivable hetero-Diels–Alder adducts only this isomer was observed, thus a prototype of a highly periselective and regioselective cycloaddition has been identified. Analysis of crude product mixtures revealed that the alpha-nitrosoalkene also adds competitively to the thioketone moiety of the thiochalcone dimer affording bis-heterocyclic [4+2]-cycloadducts. The experiments are supported by high-level DFT calculations that were also extended to related hetero-Diels–Alder reactions of other nitroso compounds and thioketones. These calculations reveal that the title cycloadditions are kinetically controlled processes confirming the role of thioketones as superdienophiles. The computational study was also applied to the experimentally studied thiochalcone dimerization, and showed that the 1,2-dithiin and 2H-thiopyran isomers are in equilibrium with the monomer. Again, the DFT calculations indicate kinetic control of this process.

15 citations

Journal Article•DOI•
Multicomponent dipolar cycloadditions: efficient synthesis of polycyclic fused pyrrolizidines via azomethine ylides

[...]

Srinivas Samala1, Do Hyun Ryu2, Choong Eui Song2, Eun Jeong Yoo3•
Kangwon National University1, Sungkyunkwan University2, Kyung Hee University3
13 Feb 2019-Organic and Biomolecular Chemistry
TL;DR: An efficient multicomponent dipolar cycloaddition for the synthesis of polycyclic fused pyrrolizidines was developed using N-aromatic zwitterions, aldehydes, and amino acids.
Abstract: An efficient multicomponent dipolar cycloaddition for the synthesis of polycyclic fused pyrrolizidines was developed using N-aromatic zwitterions, aldehydes, and amino acids. The developed reactions proceed through azomethine ylides generated in situ from the decarboxylated reactions of aldehydes and amino acids followed by the [3 + 2] cycloaddition of N-aromatic zwitterions under mild reaction conditions.

12 citations

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Stanislav Miertus1, E. Scrocco2, Jacopo Tomasi•
Slovak Academy of Sciences1, University of Pisa2
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Abstract: For neutral and charged species, atomic and molecular, a property called absolute hardness eta is defined. Let E(N) be a ground-state electronic energy as a function of the number of electrons N. As is well-known, the derivative of E(N) with respect to N, keeping nuclear charges Z fixed, is the chemical potential ..mu.. or the negative of the absolute electronegativity chi: ..mu.. = (deltaE/deltaN)/sub Z/ = /sup -/chi. The corresponding second derivative is hardness: 2eta = (delta..mu../deltaN)/sub Z/ = (deltachi/deltaN)/sub Z/ = (delta/sup 2/E/deltaN/sup 2/)/sub Z/. Operational definitions of chi and eta are provided by the finite difference formulas (the first due to Mulliken) chi = 1/2(I+A), eta = 1/2(I-A), where I and A are the ionization potential and electron affinity of the species in question. Softness is the opposite of hardness: a low value of eta means high softness. The principle of hard and soft acids and bases is derived theoretically by making use of the hypothesis that extra stability attends bonding of A to B when the ionization potentials of A and B in the molecule (after charge transfer) are the same. For bases B, hardness is identified as the hardness of the species B/sup +/. Tables ofmore » absolute hardness are given for a number of free atoms, Lewis acids, and Lewis bases, and the values are found to agree well with chemical facts. 1 figure, 3 tables.« less

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01 Jan 1934-Physica D: Nonlinear Phenomena
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Alan E. Reed1, Frank Weinhold1•
University of Wisconsin-Madison1
15 Mar 1983-Journal of Chemical Physics
TL;DR: In this paper, the authors carried out a natural bond orbital analysis of hydrogen bonding in the water dimer for the near Hartree-Fock wave function of Popkie, Kistenmacher, and Clementi, extending previous studies based on smaller basis sets and less realistic geometry.
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Slovak Academy of Sciences1, University of Pisa2
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2,168 citations

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[...]

01 Oct 2004-Synthesis
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3-Nitrochromene Derivatives as 2π Components in 1,3-Dipolar Cycloadditions of Azomethine Ylides

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Biswajit Gayen, Avijit Banerji, Kaliprasanna Dhara Budge Budge Institute of Technology, Nischintopur, Kolkata-700137 this paper, India Centre of Advanced Studies on Natural Products including Organic Synthesis, Department of Chemistry, University College of Science and Technology, University of Calcutta, 92 Acharya Prafulla Chandra Road, Kelingata-700009, India, ( Tel: 91-033-2350-8386 ; fax: 91033-2351-9