Facile preparation of 3-amino-4-(arylamino)-1H-isochromen-1-ones by a new multicomponent reaction

@article{Opatz2005FacilePO,
  title={Facile preparation of 3-amino-4-(arylamino)-1H-isochromen-1-ones by a new multicomponent reaction},
  author={Till Opatz and Dorota Ferenc},
  journal={European Journal of Organic Chemistry},
  year={2005},
  volume={2005},
  pages={817-821}
}
Reactions between 2-formylbenzoic acid, various anilines and HCN result in the formation of 3-amino-4-(arylamino)-1H-isochromen-1-ones in high yield. The mechanism of this three-component condensation involves the intermediate formation of an α-aminonitrile and subsequent cyclization through nucleophilic attack of the ortho-carboxylate at the nitrile carbon. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005) 
20 Citations
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References

SHOWING 1-10 OF 13 REFERENCES
Synthesis of 2-Aryl-3-cyanophthalimidines and Related Analogs
Abstract A series of novel 3-cyano- and related 3-substituted phthalmidines have been synthesized from acyclic precursors, some of which were isolated.
The boronic acid mannich reaction: A new method for the synthesis of geometrically pure allylamines
Abstract Reaction of vinyl boronic acids with the adducts of secondary amines and paraformaldehyde gives tertiary allylamines with the same geometry. This simple and practical method was used for theExpand
Recent Advances in Solution-Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds
Following the increased interest from the pharmaceutical industry for the generation of diverse libraries of heterocyclic compounds, scientific efforts have become more and more focused on theExpand
Neuere Methoden der präparativen organischen Chemie IV Mit Sekundär‐Reaktionen gekoppelte α‐Additionen von Immonium‐Ionen und Anionen an Isonitrile
Die mit Sekundar-Reaktionen gekoppelte α-Addition von Immonium-Ionen und Anionen (OH−, SeH−, S2O32−, N3−, NCO−, NCS−, R-CO2−, RO-CO2−) an Isonitrile ermoglicht einstufige Synthesen organischerExpand
Directional hydrogen bonding to sp2- and sp3-hybridized oxygen atoms and its relevance to ligand-macromolecule interactions
Analyse des donnees bibliographiques, sur des liaisons hydrogene O...X (X=N,O) a contacts intermoleculaires inferieurs a 3 A dans des structures contenant des groupes ether, cetone, epoxyde, enone etExpand
New hydrogen-bond potentials for use in determining energetically favorable binding sites on molecules of known structure.
TLDR
An empirical energy function designed to calculate the interaction energy of a chemical probe group with a target molecule has been developed and the shape of some of the energy functions is demonstrated on molecules of pharmacological interest. Expand
Multikomponentenreaktionen mit Isocyaniden
Multikomponentenreaktionen (MCRs) unterscheiden sich in mehreren Aspekten grundlegend von Zweikomponentenreaktionen. Unter den MCRs haben sich solche mit Isocyaniden in der pharmazeutischen IndustrieExpand
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1
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