Russian Chemical Bulletin

, Volume 60, Issue 1, pp 153–156 | Cite as

3-Hydroxy- and 3-alkoxy-2-sulfanylquinazolin-4(3H)-ones: synthesis and reactions with alkylating and acylating agents

  • P. S. Khokhlov
  • V. N. Osipov
  • A. V. Roshchin
Full Articles


Reactions of methyl 2-isothiocyanatobenzoate with hydroxylamine and alkoxyamines afforded earlier unknown 3-hydroxy-2-sulfanylquinazolin-4(3H)-one (1a) and 3-alkoxy-2-sulfanylquinazolin-4(3H)-ones (1b,c). Base-catalyzed reactions of compound 1a with alkyl halides were not regioselective, yielding O,S-dialkylation products. In the presence of acetic acid and sodium acetate, compound 1a was alkylated only at the S atom to give 2-alkylsulfanyl-3-hydroxyquinazolin-4(3H)-ones. Selective O-acylation of compound 1a at position 3 yielded 3-acyloxy-2-sulfanylquinazolin-4(3H)-ones.

Key words

quinazolinones 2-isothiocyanatobenzoate hydroxylamines cyclocondensation alkylation acylation 


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Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • P. S. Khokhlov
    • 1
  • V. N. Osipov
    • 2
  • A. V. Roshchin
    • 1
  1. 1.N. N. Semenov Institute of Chemical PhysicsRussian Academy of SciencesMoscowRussian Federation
  2. 2.N. N. Blokhin Cancer Research CenterRussian Academy of Medical SciencesMoscowRussian Federation

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