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Synthesis and reactions of new 4-chloro-2-methylpyrimidino[4′,5′:4,5]thiazolo[3,2-a]-benzimidazoles

Synthese und Reaktionen neuer 4-Chlor-2-methylpyrimidino[4′,5′:4,5]thiazolo[3,2-a]benzimidazole

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

Summary

4-Chloro-2-methylpyrimidino[4′,5′:4,5]thiazolo[3,2-a]benzimidazole (3) was prepared by chlorination of2 which could also be converted directly to 2-methylpyrimidino[4′,5′:4,5]-thiazolo[3,2-a]benzimidazol-4-thiol (4). Nucleophilic substitution of3 with alcohols, phenols, primary amines, secondary amines, sodium azide, and mercaptoacetic acid gave the corresponding derivatives. The thiol derivative4 was reacted with alkyl/aralkyl halides, phenacyl bromide derivatives, bromoacetone, chloroanilides, bromomalonic ester, and ethyl bromoacetate to afford compounds of potential pharmacological interest.

Zusammenfassung

4-Chlor-2-methylpyrimidino[4′,5′:4,5]thiazolo[3,2-a]benzimidazol (3) wurde durch Chlorierung von2, welches auch direkt zu 2-Methylpyrimidino[4′,5′:5,4]thiazolo[3,2-a]-benzimidazol-4-thiol (4) umgesetzt werden kann, hergestellt. Nucleophile Substitution von3 mit Alkoholen, Phenolen, primären Aminen, sekundären Aminen, Natriumazid und Mercaptoessigsäure ergab die entsprechenden Derivate. Das Thiolderivat4 wurde mit Alkyl/Alkarylhalogeniden, Phenacylbromidderivaten, Bromaceton, Chloraniliden, Brommalonsäureester und Bromessigsäureethylester zu potentiell pharmakologisch interessanten Verbindungen umgesetzt.

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Authors and Affiliations

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

    A. A. O. Sarhan, Z. A. Hozien, A. M. Mahmoud & H. A. H. El-Sherief

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  1. A. A. O. Sarhan
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  2. Z. A. Hozien
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  3. A. M. Mahmoud
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  4. H. A. H. El-Sherief
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Sarhan, A.A.O., Hozien, Z.A., Mahmoud, A.M. et al. Synthesis and reactions of new 4-chloro-2-methylpyrimidino[4′,5′:4,5]thiazolo[3,2-a]-benzimidazoles. Monatsh Chem 128, 1133–1141 (1997). https://doi.org/10.1007/BF00807563

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  • DOI: https://doi.org/10.1007/BF00807563

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