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Synthesis of new triazoloquinoxalines, pyrroloquinoxalines, and pyrimidopyrroloquinoxalines

Synthese neuer Triazolochinoxaline, Pyrrolochinoxaline und Pyrimidopyrrolochinoxaline

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

When 2-hydroxyquinoxaline-3-carboxamide (1) was reacted with POCl3 inDMF, 2-chloro-3-dimethylaminomethylenecarboxamide (2) was obtained. The chloro compound2 was reacted with thiourea and hydrazine hydrate to give the corresponding mercapto and hydrazino derivatives3 and8, respectively. On the other hand, 2-chloroquinoxaline-3-carbonitrile (13) reacted with ethyl glycinate to the glycinate derivative14 which was cyclized to pyrroloquinoxaline15 by heating with sodium ethoxide. Pyrimidopyrroloquinoxaline derivatives16 and17 were obtainedvia the reaction of15 with formamide and phenyl isothiocyanate, respectively.

Zusammenfassung

Wenn man 2-Hydroxychinoxalin-3-carboxamid (1) mit POCl3 inDMF reagieren läßt, erhält man 2-Chlor-3-dimethylaminomethylencarboxamid (2). Die Chlorverbindung2 wurde mit Thioharnstoff und Hydrazinhydrat zu den entsprechenden Mercapto- und Hydrazinderivaten3 und8 umgesetzt. Aus 2-Chlorchinoxalin-3-carbonsäurenitril (13) und Ethylglycinat erhält man14, das durch Erhitzen mit Natriumethylat zum Pyrrolochinoxalin15 cyclisiert wurde. Die Pyrimidopyrrolochinoxalinderivate16 und17 wurden durch Reaktion von15 mit Formamid bzw. Phenylisothiocyanat erhalten.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Assiut University, 71516, Assiut, Egypt

    A. A. Geies, A. M. K. El-Dean & O. S. Moustafa

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  1. A. A. Geies
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  2. A. M. K. El-Dean
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  3. O. S. Moustafa
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Geies, A.A., El-Dean, A.M.K. & Moustafa, O.S. Synthesis of new triazoloquinoxalines, pyrroloquinoxalines, and pyrimidopyrroloquinoxalines. Monatsh Chem 127, 1263–1272 (1996). https://doi.org/10.1007/BF00807794

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  • DOI: https://doi.org/10.1007/BF00807794

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