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Synthese und Reaktionen von 2-Amino-1-aryl-5-oxo-Δ2-pyrrolin-3-carbonitrilen

Synthesis and reactions of 2-amino-1-aryl-5-oxo-Δ2-pyrroline-3-carbonitriles

  • Organische Chemie Und Biochemie
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Summary

The reaction of malononitrile with α-chloro acetanilides1 in presence of potassium carbonate yields the 1-aryl-5-oxo-Δ2-pyrrolin-3-carbonitriles2, in presence of triethylamine the 4,6-diamino-1-aryl-2-oxo-2,3-dihydropyrrolo[2,3-b]pyridin-5-carbonitriles3 are formed. From 2-chloroacetylamino-benzencarbonitrile and malononitrile the 5-amino-1-oxo-1,2-dihydropyrrolo[1,2-a]chinazolin-3-carbonitrile (4) arise. Analogously from the 2-chloroacetylamino-thiophen-3-carbonitries5 the 7,8-dihydro-thieno[3,2-e]pyrrolo[1,2-a]pyrimidine derivatives6 are obtainable. Hydrolysis of2 a by treatment with hydroxide or acid, respectively, yields the 1,1,2-ethanetricarboxylic acid and derivatives9 a,b. Phenyldiazonium salt reacts with2 to form the triazene 7 only.

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Authors and Affiliations

  1. Sektion Chemie, Technische Universität Dresden, DDR-8027, Dresden, Deutsche Demokratische Republik

    Harry Schäfer & Karl Gewald

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  1. Harry Schäfer
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  2. Karl Gewald
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Schäfer, H., Gewald, K. Synthese und Reaktionen von 2-Amino-1-aryl-5-oxo-Δ2-pyrrolin-3-carbonitrilen. Monatsh Chem 120, 315–322 (1989). https://doi.org/10.1007/BF00811744

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  • DOI: https://doi.org/10.1007/BF00811744

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