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Search for "spirooxindole" in Full Text gives 32 result(s) in Beilstein Journal of Organic Chemistry.

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

  • Chuqin Peng,
  • Jiwei Ren,
  • Jun-An Xiao,
  • Honggang Zhang,
  • Hua Yang and
  • Yiming Luo

Beilstein J. Org. Chem. 2014, 10, 352–360, doi:10.3762/bjoc.10.33

Graphical Abstract
  • 4-nitrobenzoic acid, respectively. The substituent effects on the regioselectivity were also investigated. Keywords: 1,3-dipolar cycloaddition; azomethine ylide; regioselectivity; spirooxindole; Introduction Spirooxindoles are important synthetic targets due to their significant biological
  • employed as starting materials to conduct 1,3-dipolar cycloadditions to yield spirooxindole core structures [16][17][18][19][20]. Owing to the ease of preparation, the azomethine ylides generated from isatin with α-amino acids or amines were frequently chosen as important 1,3-dipolar intermediates to react
  • spirooxindoles in good to excellent chemical yields with good regioselectivities. Furthermore, the regioselectivity can be conveniently tuned and reversed by simply adding water or 4-nitrobenzoic acid, which provides a facile approach to access a wide range of spirooxindole ring systems with novel substitution
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Letter
Published 07 Feb 2014

The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids

  • Tatyana L. Pavlovskaya,
  • Fedor G. Yaremenko,
  • Victoria V. Lipson,
  • Svetlana V. Shishkina,
  • Oleg V. Shishkin,
  • Vladimir I. Musatov and
  • Alexander S. Karpenko

Beilstein J. Org. Chem. 2014, 10, 117–126, doi:10.3762/bjoc.10.8

Graphical Abstract
  • and CCDC 972494 for 6a). The NOE correlations of the signals in 1H NMR spectra of compounds 4b–4d. Molecular structure of spirooxindole 4a according to X-ray diffraction data. The NOE correlations of the signals in 1H NMR spectrum of compound 6c. Molecular structure of spirooxindole 6a observed in
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Published 09 Jan 2014

Facile synthesis of functionalized spiro[indoline-3,2'-oxiran]-2-ones by Darzens reaction

  • Qin Fu and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 918–924, doi:10.3762/bjoc.9.105

Graphical Abstract
  • ; oxindole; oxirane; spiro-epoxyoxindole; spirooxindole; Introduction The spirooxindole unit is a privileged heterocyclic motif that forms the core structure of a large family of natural alkaloids and many pharmacological agents with important bioactivity and interesting structural properties [1][2][3][4][5
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Published 13 May 2013

Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

  • Yan Sun,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 8–14, doi:10.3762/bjoc.9.2

Graphical Abstract
  • scope of this novel reaction is briefly discussed. Keywords: arylamine; cyclopentanedione; isatin; multicomponent reaction; spiro compound; Introduction The spirooxindole is among the most important class of naturally occurring substances, characterized by highly pronounced biological properties, and
  • is also the core structure of many synthetic pharmaceuticals [1][2]. The various biological activities of spirooxindole derivatives have attracted much attention from organic chemists, and as a consequence, a number of methods have been reported for the preparation of spirooxindole-fused heterocycles
  • derivatives have become an efficient method for the synthesis of various spirooxindoles in recent years [9][10]. It is known that the multicomponent reactions of isatins with in situ formed azomethine ylides have become the efficient synthetic procedure for constructing versatile spirooxindole systems [11][12
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Published 03 Jan 2013

Expanding the chemical diversity of spirooxindoles via alkylative pyridine dearomatization

  • Chunhui Dai,
  • Bo Liang and
  • Corey R. J. Stephenson

Beilstein J. Org. Chem. 2012, 8, 986–993, doi:10.3762/bjoc.8.111

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  • Chunhui Dai Bo Liang Corey R. J. Stephenson Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA 10.3762/bjoc.8.111 Abstract A mild and practical synthesis of spirooxindole [1,3
  • ; 1,3-dicarbonyl compounds; Diels–Alder reaction; molecular diversity; pyridine dearomatization; spirooxindole; Introduction The spirooxindole is a common structural motif found in a variety of complex alkaloids [1]. Many compounds that possess a spirooxindole moiety exhibit significant biological
  • ], we previously reported a Lewis acid catalyzed, three-component synthesis of spirooxindole pyranochromenedione derivatives using isatin and two 1,3-dicarbonyl compounds (Scheme 1) [14]. Mechanistically, we believed this reaction to proceed through an intermediate isatylidene 1 [15][16][17]. As a means
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Published 02 Jul 2012

Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles

  • Kay M. Brummond and
  • Joshua M. Osbourn

Beilstein J. Org. Chem. 2011, 7, 601–605, doi:10.3762/bjoc.7.70

Graphical Abstract
  • oxindoles into chiral non-racemic spirooxindoles containing an alkylidene cyclobutene moiety. The enantiomeric excesses were determined by chiral lanthanide shift NMR analysis and the transfer of chiral information from the allene to the spirooxindole was found to be greater than 95%. Keywords: alkylidene
  • spirooxindole-containing skeletons 2 in a two-step one-pot process from propargyl acetates 1 [4] (Scheme 1). Inspired by this rapid entry into the molecularly complex substructure 2, and the structural similarity to welwitindolinone A isonitrile (3), we became interested in the synthesis of chiral non-racemic
  • spirooxindoles for application to natural product synthesis [5][6][7]. Herein, we disclose preliminary results demonstrating a complete transfer of chiral information from a chiral non-racemic allene-yne to form an enantiomerically enriched spirooxindole in a [2 + 2] cycloaddition reaction. Findings This study
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Published 12 May 2011

A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles

  • Kay M. Brummond and
  • Joshua M. Osbourn

Beilstein J. Org. Chem. 2010, 6, No. 33, doi:10.3762/bjoc.6.33

Graphical Abstract
  • observed, but are likely intermediates of an infrequently encountered thermal [3,3]-sigmatropic rearrangement of a propargylic acetate. Keywords: allene; propargylic acetate; spirooxindole; thermal [2 + 2] cycloaddition; thermal [3,3]-sigmatropic rearrangement; vinylidene indolin-2-one; Introduction
  • , the feasibility of this method for the preparation of spirooxindole alkaloids was investigated. The preliminary results of this study are reported herein. Results and Discussion To begin the investigation, the first challenge was the preparation of a functionalized vinylidene indolin-2-one 5 (Figure 2
  • of the resulting propargyl alcohol. Heating propargylic acetate 9a to 225 °C in 1,2-dichlorobenzene in the microwave for 30 min gave the spirooxindole 10a in 60% yield (Scheme 2). Structural confirmation of 10a was achieved using COSY, HMQC and HMBC. Attempts to effect the [3,3]-sigmatropic
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Preliminary Communication
Published 08 Apr 2010
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