Abstract
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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
S. Eguchi; in Topics in Heterocyclic Chemistry, Ed. S. Eguchi, Springer, Berlin, 2006, 6, 113.
J. P. Michael, Nat. Prod. Rep., 2007, 24, 223.
G. W. Rewcastle, in Comprehensive Heterocyclic Chemistry, Eds A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor, Elsevier, Oxford, 2008, 8, 117.
D. J. Brown, in Chemistry of Heterocyclic Compounds, Ed. E. C. Taylor, John Wiley and Sons, Inc., New York, 1996, 55.
RU Pat. 2 275 362, Byull. Izobret., 2006, 12; Chem. Abstrs, 2006, 144, 390940.
L. N. Tumey, D. Bom, B. Huck, E. Gleason, J. Wang, D. Silver, K. Brunden, S. Boozer, S. Rundlett, B. Sherf, S. Murphy, T. Dent, C. Leventhal, A. Bailey, J. Harrington, Y. L. Bennani, Bioorg. Med. Chem. Lett., 2005, 15, 277.
T. P. Tran, E. L. Ellsworth, M. A. Stier, J. M. Domagala, H. D. H. Showalter, S. J. Gracheck, M. A. Shapiro, T. E. Joannides, R. Singh, Bioorg. Med. Chem. Lett., 2004, 14, 4405.
V. Colotta, D. Catarzi, F. Varano, F. R. Calabri, G. Filac- chioni, C. Costagli, A. Galli, Bioorg. Med. Chem. Lett., 2004, 14, 2345; I. L. Dikii, O. S. Kris’kiv, V. P. Chernikh, L. A. Shemchuk, N. V. Dubinina, Visn. Farm. [Bull. Pharm.], 2006, 2, 64 (in Ukrainian).
A. V. Kotov, V. V. Zakharychev, A. G. Smirnov, V. I. Fetis- ov, P. B. Gordeev, O. A. Luk’yanov, A. L. Chimishkyan, I. V. Martynov, Dokl. Akad. Nauk, 2001, 381, 694 [Dokl. Chem. (Engl. Transl.), 2001, 381].
P. N. Pohorgava, S. N. Singh, Egypt. J. Chem., 1972, 15, 495.
R. K. Saksena, A. Khan, Indian J. Chem., 1988, 27B, 295.
S. Senda, A. Suzui, Chem. Pharm. Bull., 1958, 6, 47
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 146–149, January, 2011.
Rights and permissions
About this article
Cite this article
Khokhlov, P.S., Osipov, V.N. & Roshchin, A.V. 3-Hydroxy- and 3-alkoxy-2-sulfanylquinazolin-4(3H)-ones: synthesis and reactions with alkylating and acylating agents. Russ Chem Bull 60, 153–156 (2011). https://doi.org/10.1007/s11172-011-0022-1
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-011-0022-1