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Search for "azetidines" in Full Text gives 8 result(s) in Beilstein Journal of Organic Chemistry.

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

  • Péter Kisszékelyi and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

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  • azetidines 19 were also synthesized using this methodology (Scheme 5b). Nitronate anions were also found suitable for Mannich-type trapping reactions [28][29]. Anderson and co-workers accomplished several Cu-catalyzed conjugate additions of R2Zn to nitroolefins 20, followed by subsequent reaction with p
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Published 04 May 2023

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

  • Joseane A. Mendes,
  • Paulo R. R. Costa,
  • Miguel Yus,
  • Francisco Foubelo and
  • Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

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  • azetidines Azetidine [76][77] has attracted less attention than aziridines, pyrrolidines and piperidines, among small and medium size aza-heterocycles, because there are no general methods for their preparation. However, four-membered nitrogen-containing heterocycles have recently found applicability in
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Published 12 May 2021

Recent synthesis of thietanes

  • Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

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  • reagent for the nucleophilic ring expansion of three-membered heterocycles. It was successfully applied in the preparation of oxetanes and azetidines via the ring expansions of oxiranes [116][117][118] and aziridines [119][120]. However, both thiiranes and thietanes were less stable than the corresponding
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Published 22 Jun 2020

Accelerating fragment-based library generation by coupling high-performance photoreactors with benchtop analysis

  • Quentin Lefebvre,
  • Christophe Salomé and
  • Thomas C. Fessard

Beilstein J. Org. Chem. 2020, 16, 982–988, doi:10.3762/bjoc.16.87

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  • of complex amines: bicyclopentanamines, azetidines, spiroazetidines, spiropyrrolidines and spiropiperidines. Functional group tolerance was probed by using functionalized building blocks bearing esters, carbamates, alcohols, tertiary amines, ethers, sulfones and fluorine atoms (Scheme 2 and Scheme 3
  • electrochemically-mediated nickel-catalyzed cross-couplings. Electron-deficient aniline products are less prone to oxidative decomposition. BCP-amines were viable coupling partners but gave the corresponding products 1a–e in poor purities. Simple azetidines partook the reaction to give 2a–c while azaspiro[3,3
  • to nickel(0) is believed to occur by β-hydride elimination on a sacrificial amount of amine [10]. The strained character of azaspiro[3,3]heptane might prevent this event. On the other hand, pyramidalization at nitrogen is much more important in azetidines [16][17][18]. This might lower the oxidation
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Published 12 May 2020

Oxidative radical ring-opening/cyclization of cyclopropane derivatives

  • Yu Liu,
  • Qiao-Lin Wang,
  • Zan Chen,
  • Cong-Shan Zhou,
  • Bi-Quan Xiong,
  • Pan-Liang Zhang,
  • Chang-An Yang and
  • Quan Zhou

Beilstein J. Org. Chem. 2019, 15, 256–278, doi:10.3762/bjoc.15.23

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  • presence of 2-indobenzoic acid anion. Recently, Shi’s group developed the first ring expansion of MCPs 63 with a nitrogen atom to furnish azetidines 64 (Scheme 14) [82]. The author proposed that Rh(II) had an effective impact on the reactions and could improve the reaction yields. Unfortunately, the MCPs
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Published 28 Jan 2019

Studies on the interaction of isocyanides with imines: reaction scope and mechanistic variations

  • Ouldouz Ghashghaei,
  • Consiglia Annamaria Manna,
  • Esther Vicente-García,
  • Marc Revés and
  • Rodolfo Lavilla

Beilstein J. Org. Chem. 2014, 10, 12–17, doi:10.3762/bjoc.10.3

Graphical Abstract
  • ring system. The scope of the reaction regarding the imine and isocyanide ranges has been determined, and also some mechanistic variations and structural features have been described. Keywords: azetidines; heterocycles; imines; isocyanides; multicomponent reactions; Introduction The interaction of
  • interest in the azetidine scaffold in medicinal chemistry [9], we decided to study in detail the formation of bis(imino)azetidines 3 from the interaction of imines 1 and isocyanides 2 (Scheme 1), including the scope of the reaction and mechanistic features of this interesting ABB’ process [10]. Results and
  • isatinimines led to the formation of the spiro-azetidines 3k (14%) and 3l (28%, Table 1, entries 11 and 12). Remarkably, in the former case an intramolecular cyclization of the nitrilium ion upon the electron rich p-methoxyphenyl group took place and led to the formation of the bis(imino)tetrahydroquinoline 8
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Published 06 Jan 2014

Stereoselectively fluorinated N-heterocycles: a brief survey

  • Xiang-Guo Hu and
  • Luke Hunter

Beilstein J. Org. Chem. 2013, 9, 2696–2708, doi:10.3762/bjoc.9.306

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  • transpires that this C–F…N+ interaction is a general effect which has also been observed in larger N-heterocycles, as discussed below. 3.2 Five-membered rings The C–F…N+ interaction can have a more dramatic impact on the conformations of pyrrolidines, since they are inherently more flexible than azetidines
  • axial conformers are preferred by a substantial ~5.0 kcal/mol over the equatorial conformers (not shown) [28][29]. This pioneering work constituted the original discovery of the C–F…N+ interaction which has already been discussed above in the context of azetidines and pyrrolidines. Interestingly, Lankin
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Published 29 Nov 2013

Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity

  • Matthias D’hooghe,
  • Stéphanie Vandekerckhove,
  • Karen Mollet,
  • Karel Vervisch,
  • Stijn Dekeukeleire,
  • Liesbeth Lehoucq,
  • Carmen Lategan,
  • Peter J. Smith,
  • Kelly Chibale and
  • Norbert De Kimpe

Beilstein J. Org. Chem. 2011, 7, 1745–1752, doi:10.3762/bjoc.7.205

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  • -ones with a focus on stereoselectivity, thus providing convenient entries into, e.g., aziridines, azetidines and β-aminoalcohols [28][29][30][31]. In continuation of our interest in the use of functionalized β-lactams as synthons for further elaboration, racemic trans-4-aryl-3-chloro-β-lactams 5 were
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Published 30 Dec 2011
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