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

被引：2
|
作者：
Khokhlov, P. S. [1 ]
Osipov, V. N. [2 ]
Roshchin, A. V. [1 ]
机构：
[1] Russian Acad Sci, NN Semenov Chem Phys Inst, Moscow 119991, Russia
[2] Russian Acad Med Sci, NN Blokhin Canc Res Ctr, Moscow 115446, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2011年 / 60卷 / 01期
关键词：
quinazolinones; 2-isothiocyanatobenzoate; hydroxylamines; cyclocondensation; alkylation; acylation; QUINAZOLINE; ALKALOIDS;
D O I：
10.1007/s11172-011-0022-1
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
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页码：153 / 156
页数：4
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