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Search for "isatin" in Full Text gives 79 result(s) in Beilstein Journal of Organic Chemistry.

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

Graphical Abstract
  • ], 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
  • with isatin and 1,3-cyclohexanedione (5a) as coupling partners, we isolated a relatively poor yield of product 6a (Table 1, entry 1). We speculated that the free indole nitrogen was inhibiting the reaction, thus we switched to N-substituted isatins and found that the reaction improved to provide
  • moderate to high yields (Table 1, entries 2–10). Subtle substitution effects were observed when the C(5)–H of isatin was replaced with various functionalities. Specifically, an electron-donating group at the 5-position, such as a methyl group, decreased the reactivity and only gave 57% yield (Table 1
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Letter
Published 02 Jul 2012

An intramolecular inverse electron demand Diels–Alder approach to annulated α-carbolines

  • Zhiyuan Ma,
  • Feng Ni,
  • Grace H. C. Woo,
  • Sie-Mun Lo,
  • Philip M. Roveto,
  • Scott E. Schaus and
  • John K. Snyder

Beilstein J. Org. Chem. 2012, 8, 829–840, doi:10.3762/bjoc.8.93

Graphical Abstract
  • Intramolecular inverse electron demand cycloadditions of isatin-derived 1,2,4-triazines with acetylenic dienophiles tethered by amidations or transesterifications proceed in excellent yields to produce lactam- or lactone-fused α-carbolines. Beginning with various isatins and alkynyl dienophiles, a pilot-scale
  • library of eighty-eight α-carbolines was prepared by using this robust methodology for biological evaluation. Keywords: α-carboline; chemical diversity; inverse electron demand Diels–Alder; isatin; pyrido[2,3-b]indole; 1,2,4-triazine; Introduction In comparison with the well-known β-carbolines, α
  • library of annulated α-carboline structures 6 could be prepared by the intramolecular inverse electron demand Diels–Alder reaction (IEDDA) of isatin-derived 1,2,4-triazines 7 with tethered electron-rich dienophiles (Scheme 1) [69]. Inverse electron demand Diels–Alder cycloadditions employing electron
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Full Research Paper
Published 06 Jun 2012

Novel tetracyclic structures from the synthesis of thiolactone-isatin hybrids

  • Renate Hazel Hans,
  • Hong Su and
  • Kelly Chibale

Beilstein J. Org. Chem. 2010, 6, No. 78, doi:10.3762/bjoc.6.78

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  • 7701, South Africa 10.3762/bjoc.6.78 Abstract A simple and straightforward synthetic approach to potential anti-infective thiolactone-isatin hybrids led to the discovery of novel tetracyclic compounds which bear a macrocylic motif containing an unusual bridged amide bond. Keywords: bridged amides
  • ; hybrids; isatin; tetracycles; thiolactomycin; thiolactone; Introduction Hybrid structures have been found in nature and their synthesis has become a useful drug discovery strategy for new anti-infective agents [1]. Improved pharmacokinetics, therapeutic and toxicity profiles have been reported for
  • natural and natural product-like hybrid constructs such as the artemisinin-quinine [2], nostocarboline-ciprofloxacin [3] and isatin-lamuvidine [4] (Figure 1). Interest in exploring this approach also derives from the pharmacophore-rich compound library it offers. This precludes the need for large
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Full Research Paper
Published 19 Jul 2010

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
  • 5 could be obtained by way of a thermal [3,3]-sigmatropic rearrangement of the propargylic acetate 6 to give compound 5 where R2 = OAc (Figure 2) [27]. Preparation of propargylic acetate 9a was accomplished by the addition of the lithium acetylide of 8 to N-methyl isatin (7) followed by acetylation
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Preliminary Communication
Published 08 Apr 2010
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