DD221737A1 - PROCESS FOR PREPARING 2-ARYL-1,4-DIHYDRO-CHINAZOLIN-4-ON-1-EATING-ACID ESTERS - Google Patents

Abstract

The aim of the invention is to provide new biologically active 1,4-dihydro-quinazolin-4-one-1-acetic acid esters in practice as active ingredients. According to the invention, a 1-alkoxycarbonylmethyl isatozoic anhydride is reacted with an arylamidine or its salt to give a 2-aryl-1,4-dihydro-quinazolin-4-one-1-acetic acid ester of the general formula II while being heated in solution, suspension or melt. These compounds are of interest to medicine, the pharmaceutical industry and agriculture, horticulture and forestry. Formula I and II

Description

Process for the preparation of 2-aryl-1,4-dihydro-quinazolin-4-one-1-acetic acid esters

The invention "relates to a process for the preparation of 1-dihydro-quinazolin-1-one-acetic acid esters of the general formula II, which have an aryl group in the 2-position.

Field of application of the invention

The invention is of interest to medicine, the pharmaceutical industry and agriculture and horticulture and forestry. '· - .. -' · '..:: ^; '' ". '' ·· ':

Characteristics of the most well-known technical solutions

A large number of quinazolines are already used in pharmaceutical practice (S. JOHNE, Pharmazie 36, 585 (1981); S. JOHNE, Fortschr. Arzneimittelforschung 26, 259 (1982)). Other quinazolines have a potential effect as phyto-effectors, fungicides, acaricides, insecticides or herbicides (M.SUSSE and S. JOHNE, Z. Chem. 21, 431 (1981)). Compounds of general formula II are not known.

1st object of the invention to provide novel biologically active 1,4-Dih5 ^r dro-quinazolin-4-on-i-essigsäureester practice as active ingredients available.

Explanation, the essence of the invention

The object of the invention is to develop a process for the preparation of 2-aryl-i ₅ 4-dihydro-quinazolin-4-one-1-acetic acid esters of general formula II.

According to the invention, an i-alkoxycarbonylmethyl-isatoic anhydride. of the general formula I with an arylamidine or its salt in solution or suspension in an organic solvent with heating or in the melt to form an ester of the general formula II. In the general formulas I and II are R, for alkyl, R is halogen, alkyl, alkoxy, OH, R ^{J is} aryl (optionally substituted) and η is 0 to 4, wherein in the cases η = 2, 3 or 4 the R are the same or different. Suitable solvents are both polar protic and dipolar aprotic organic solvents. In general, it works at the boiling point of the solvent «,.

If the salts of arylamidines are used, the addition of the equivalent amount of an auxiliary base, for example soda, potash or a tertiary organic base, such as pyridine or triethylamine, is necessary. In the case of using an organic base, the auxiliary base can be used simultaneously as solvent.

The starting materials for the novel process are commercially available products or can be prepared in a simple ^one way.

The compounds of general formula II are new and biologically active. Among them are those which have a fungicidal, plant growth regulatory or anti-allergic effect. It is also possible to use the compounds of general formula II prepared in the form of their acids or their salts (R = H or metal or NH.), Because the esters of the general formula II can be in a simple manner by hydrolysis in the corresponding Transfer acids.

The invention will be explained below by some embodiments.

Exemplary embodiment ;

2.1 g of benzamidine hydrochloride, 3.4 g of 1-ethoxycarbonylmethyl-3, t-benzoxa2iin-2,4-dione (I: R = C ₂ Hk, n = 0) are refluxed with 60 ml of pyridine for 10 hours. The pyridine is distilled off in vacuo, the residue is mixed with water, filtered off with suction and crystallized. E.thanol / water around. M.p. 153-154 ⁰ C; Yield: 2.6 g 1 ^ -dihydro ^ -phenylchinazolin-4-one-1-acetic acid (II: R = 0 _{9 Η} ς "n = 0, R ⁼ CßHc.).

Beisiel_2 '·' ..,: '^;':':

1 g of 4-hydroxybenzamidine hydrochloride, 1.4 g of 1-methoxycarbonylmethyl-3,1-benzoxazine-2,4-dione (I: R ¹ = CH-, n = 0) and 0.6 g of triethylamine are refluxed in DBIF for 2 hours. DMF is distilled off in vacuo, the residue is mixed with water, filtered off and recrystallized from ethanol. . Mp 284-287 ⁰ C, yield: 0.3 g of 1,4-dihydro-2- (4-hydroxy-phenyl) -ehinazolin-4-one-1-acetic acid (II: R = CH ^, n = 0, R = 4-HO-C ₆ H ₄ ). '/,,

For this 1 page formulas

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Claims (4)

Erf indungsanspruoli 1. A process for the preparation of 2-aryl-1,4-dihydro-quinazolin-4-one-1-acetic acid esterified, characterized in that a 1-Alkoxycarbonylmethy! -Isatosäureanhydrid of the general formula I with an arylamidine or its salt in solution or suspension in an organic solvent with heating or in the melt to give a compound of general formula II, wherein in the formulas I and II R ^{1 is} alkyl, R ^{2 is} halogen, alkyl, alkoxy, OH, R is aryl (optionally substituted ) and η are 0 to 4, whereby in the case of 2 '' '' 'len η = 2, 3 or 4, the R are the same or different. 2. The method according to item 1, characterized, 'that, the reaction is carried out at the boiling temperature of the solvent. , 3. Method according to item 1 or 2, characterized in that an auxiliary base is added. 4. The method according to item 3, characterized in that a tertiary organic base is used as the auxiliary base, which is also solvent.