SU589913A3 - Method of preparing nitro-quinazolinone derivatives - Google Patents

Description

  , 1 The invention relates to the method of pbpuchi new derivatives of nigroquinazopinonafor mupa. , CnBgtrTR-S where R is a halogen atom, a hydrogen atom, a lower apkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a trifluoromethyl group or a nitro group; a fepq group, unsubstituted or substituted by a halogen atom, a lower alkyl group, a lower alkoxy group, or a nitro group; a cycloalkyl group or a thienyl group; - an unsubstituted or substituted 5cpi 6-membered heterocyclic ring containing one heteroatom selected from the groats containing a nitrogen, oxygen or sulfur atom; And - an integer from O to 3, which have biological activity and can be used in medicine. Nitroquinazolone derivatives are known in the literature, which (have no biologically active properties til. The purpose of the invention is a method of producing new nitroquinazolinone G1 derivatives that can be used as biologically active compounds. The proposed method of obtaining compounds of formula (1) is because that the compounds of the formula (ii) N — CO — C — Xo 3 where R |, I, and Rj have the above values and each of X ,, Xj or Xj is an atom g of the gene, are reacted with ammonia. in the presence of p solvent: or solvent mixtures. Methanop, ethanol, isopropane, tert-butanol, 2-ethoxyethanop, tetrahydrofuran, cyoxane, acetone, pyridine, toluene, dimethyl sulphoxide and dimethylformamide or their mixtures are used as a solvent. ammonia gas, ammonia alcohol solution (for example, in methanol or ethanol), liquid ammonia or ammonium salt (for example, in the form of ammonium acetate, ammonium formate, ammonium carbamate or ammonium phosphate). When using an ammonium salt, the reaction can be carried out in the presence of a base, for example, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium metipate, sodium ethylate, kapi ethylate, triethipamine or pyridine. The process can be carried out at room temperature, at elevated or lowered temperatures. The starting compounds are new compounds which are obtained by reacting a compound of the formula: NH-CnH2 "-R.3 where RJ, and R have the above values, with trihaloacetic acid or its reactive derivative of the formula Xg-C-COOH (JV) where Xj, X and Xj have the above. cheni. Example 1. A mixture of 2.36 g of 2- (M-tetrahydrofurfuryl-trichloroacetamido) -5-nit. Trobenzophenone, 2.4 g of ammonium acetate, 0.5 g of triethipamine and 30 ml of ethanol is stirred under reflux for 10 hours. The solvent is then removed and water is added to the residue. The mixture is extracted with chloroform and the extract is washed successively with a dilute aqueous solution of ammonia a and water, and then dried over anhydrous sodium sulfate. The solvent is removed in vacuo. The residue is washed with ether and the insoluble product is collected by filtration and dried. Teach 1-tetrahydrofurfuryl-4-phenyl-6-nitroquinazolinone-2 (1H) c. m.p. 150152 ° C. Example 2. The following compounds were prepared according to the method described in Example 1; . 1-tetrahydropyran-2yl-methyl-4-phenyl-6-nitro-2 (1H) -quinazoline, m.p. 186-187 ° C; 1-furfuryl-4-phenyl-6-nitro-2 (1H) -quinazolinone; mp. 189-19 ° C; 1- (2-pyridipmethyl) -4-phenyl-6-nitro-2 (1H) quinazolinone, t, pl. 175-17b C; 1- (3-pyridipmethyl) -4-phenyl-6-nitro-2 (1H) ™ quinazopinone; m.p. 204-205 ° C; 1-tetrahydropyran-2 yl-methyl - 4- (2-thienip) 6-nig o-2 (1H) -quinazolinone, so pl. 208.52О9, 5 С, as well as the compounds indicated in t.ppitsa, continuation of the table

-CHg-O

-SngSNg-o-SeNb -sne-

Also

CHgSOHj

- w

C1

Claims (3)

-o Claim 1, A method for producing nitroquinazolinone derivatives of the formula nHgn C-3. where R is a hydrogen atom, a halogen atom, nieshai. alkyl group, lower alkoxygrut pa, lower apkylthio group, lower alkypsuPiFo nipnu group, trifluoromethyl group or nitro group ;: I, is a phenyl group unsubstituted or substituted by a halogen atom, a lower anp group, a lower alkoxy group or a nitro group; a cycloalkyl group or a thienyl group, G an unmixed or substituted 5 or b-membered hetero ring, containing one heteroatom selected from the group containing an atom of nitrogen, oxygen or sulfur, and an integer from 0 to 3, oo l and h ay and with the fact that the compound of the formula, f CO-C-X2 (l) where K, K, R and P have the above values, and each of X, Xj or X is a halogen atom is reacted with ammonia,. . 2. The method according to claim 1, wherein the process is carried out in the presence of a solvent or mixture of solvents, 3. The method according to claim 2, wherein the solvent is methanol, ethanol, isopropanol, and tert. butane, 2-ethoxyethanoP | tetrag Drofuran, rc ocean, acetone, pyridine, benzop, toluene, methyl sulfoxide, dimethylformide or mixtures thereof. Sources of information taken into account in the examination: 1, UK Patent N 1251600, cl. C2C, 27, .10. 1971.