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Search for "Gewald reaction" in Full Text gives 5 result(s) in Beilstein Journal of Organic Chemistry.

Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide

  • Marios Zingiridis,
  • Danae Papachristodoulou,
  • Despoina Menegaki,
  • Konstantinos G. Froudas and
  • Constantinos G. Neochoritis

Beilstein J. Org. Chem. 2025, 21, 217–225, doi:10.3762/bjoc.21.13

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  • structure was obtained, revealing certain geometrical features. Keywords: 2-amino-substituted heterocycles; cyanoacetamide; Gewald reaction; multicomponent reaction (MCR); pyrimidine; Introduction The term “net-zero carbon” is becoming increasingly common as we consider a future marked by a rising global
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Published 24 Jan 2025

Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

  • Lucía Campos-Prieto,
  • Aitor García-Rey,
  • Eddy Sotelo and
  • Ana Mallo-Abreu

Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261

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  • deacetylase substrate MAL to determine the inhibitory activity, and using sirtinol as positive control. When compared to sirtinol (IC50 = 67 µM), selected compounds showed moderate affinity towards SIRT2, with IC50 values ranging from 118 to 126 µM (Figure 10). Gewald reaction: Cannabinoid receptors have been
  • new selective non-cannabinoid ligands due to the important motor impairment found in mice lacking GPR55 [51]. In this context, ML192 analogs were synthesized employing a divergent synthetic route starting with a multicomponent reaction, the Gewald reaction (Scheme 13). This reaction allows to easily
  • build the principal heterocycle of the compounds. Good reaction yields (70–87%) made it possible to obtain the aminothiophene carboxylates necessary for the following steps of the route [52]. Some of the intermediates of the Gewald reaction were oxidized to provide further exploration of the
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Review
Published 03 Dec 2024

Thiazole formation through a modified Gewald reaction

  • Carl J. Mallia,
  • Lukas Englert,
  • Gary C. Walter and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2015, 11, 875–883, doi:10.3762/bjoc.11.98

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  • The synthesis of thiazoles and thiophenes starting from nitriles, via a modified Gewald reaction has been studied for a number of different substrates. 1,4-Dithiane-2,5-diol was used as the aldehyde precursor to give either 2-substituted thiazoles or 2-substituted aminothiophenes depending on the
  • substitution of the α-carbon to the cyano group. Keywords: design of experiment (DOE); 1,4-dithiane-2,5-diol; Gewald reaction; thiazole; thiophene; Introduction Thiazoles are privileged motifs which are encountered in many naturally occurring bioactive compounds and pharmaceuticals with indications in a
  • original Gewald reaction mechanism. Mechanism B would also be viable for molecules which possess no protons α to the nitrile group. The fact that compounds 46 and 47 did not react implies mechanism A is the predominant pathway. The lack of reactivity of substrate 47 can be attributed to the high degree of
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Published 26 May 2015

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

  • Marcus Baumann,
  • Ian R. Baxendale,
  • Steven V. Ley and
  • Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

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Review
Published 18 Apr 2011

A facile synthesis and fungicidal activities of 2-(alkylamino)-5,6-dimethylthieno[2,3-d]pyrimidin- 4(3H)-ones

  • Yang-Gen Hu,
  • Ai-Hua Zheng,
  • Xu-Zhi Ruan and
  • Ming-Wu Ding

Beilstein J. Org. Chem. 2008, 4, No. 49, doi:10.3762/bjoc.4.49

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  • attention because their starting materials, 2-amino-3-carboxythiophenes, can be conveniently synthesized by Gewald reaction [10]. Synthetically useful approaches to thienopyrimidinones starting from easily accessible 2-amino-3-carboxythiophenes are therefore of great importance. Recently we have been
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Preliminary Communication
Published 08 Dec 2008
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