KR840006218A - Method for preparing ortho-substituted dihydroxy-2 (1H) quinazolinone-1-alkanoic acid - Google Patents

Abstract

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Description

Method for preparing ortho-substituted dihydroxy-2 (1H) quinazolinone-1-alkanoic acid

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Claims (27)

The compound of formula (1) and its phenolic hydroxide are characterized by reacting a compound of formula (1) with an olefin of formula (A) in the presence of a base to form a compound of formula (2) and reacting it with an acid. Selected amine salts, ethanolamines, such as allyl metal and alkaline earth metal salts of carboxyl and carboxy groups of N-1, meglumine, pyreazine, N-methylpiperazine, morpholine and salts of aliphatic amines having 1 to 5 carbon atoms, A process for preparing salts of aminoalcohols such as 2-amino-1,3-propanediol and bis (hydroxymethyl) methylamine, and salts with amino acids such as arginine, lysine and ornithine. Wherein R is hydrogen or methyl; R ₁ is hydrogen, amino and nitro; R ₂ is hydrogen, alkyl, cycloalkylalkyl, cycloalkyl, haloalkyl and bicycloalkyl; R ₃ and R ₄ are the same or different and are hydrogen, lower alkyl, aryl and substituted aryl; X is benzyl, carboxy, carboalkoxy, cyano, carboxytemido, methanesulfonyl, formyl, alkanoyl, aroyl and heteroaroyl and heteroaryl. The process of claim 1 wherein the olefin is selected from methyl cinnamates, methylacrylates, methylcrotonates and acrylonitrile. The method of claim 1 wherein the acid is hydrobromic acid. A process for preparing a compound of formula (3), wherein the compound of formula (2) is reacted with an iodide of formula (B) and then the product is reacted with an acid. Wherein R is lower alkyl; R ₁ is hydrogen, amino or nitro; R ₂ is hydrogen, cycloalkylalkyl, alkyl, cycloalkyl, haloalkyl and bicycloalkyl; R ₃ and R ₄ are the same or different and are hydrogen, lower aryl, substituted aryl; R ₅ is lower alkyl, benzyl or substituted benzyl; X is benzyl, carboxy, carboalkoxy, cyano, carboxamido, methanesulfonyl, formyl, alkanoyl, aroyl, heteroaroyl and heteroaryl. The method of claim 4, wherein R ₅ is benzyl. The method of claim 4, wherein the acid is hydrobromic acid. The compound of formula (1) is reacted with the olefin of formula (A) to form a compound of formula (2), which is reacted with the iodide of formula (B), and then the product is reacted with hydrohalic acid. A process for preparing the compound of formula (4), characterized by producing a salt of formula (3 ') and hydrogenating it. Wherein R is lower alkyl; R ₁ is hydrogen, amino or nitro; R ₂ is hydrogen, cycloalkylalkyl, alkyl, cycloalkyl, haloalkyl and bicycloalkyl; R ₃ and R ₄ are the same or different and are hydrogen, lower alkyl, aryl and substituted aryl; R ₅ is lower alkyl, benzyl or substituted benzyl; X is benzyl, carboxy, carboalkoxy, cyano, carboxamido, methanesulfonyl, formyl, alkanoyl, aroyl, heteroaroyl and heteroaryl. 8. The process of claim 7, wherein the hydrohalic acid is hydrogen bromide. 8. The method of claim 7, wherein the iodide is methyl iodide. 8. The process according to claim 7, wherein the olefins are methylcinnamate, methylacrylate, methylcrotonate and acrylonitrile. The method of claim 1, wherein the 6,7-dihydroxy-4-methyl-2 (1H) quinazolinone-1-propionic acid is prepared. The method of claim 1, wherein the 6,7-dihydroxy-4-trifluoromethyl-2 (1H) quinazolinone-1-propionic acid is prepared. The method of claim 1, wherein 6,7-dihydroxy-4-octyl-2 (1H) quinazolinone-1-propionic acid is prepared. The method of claim 1, wherein the 6,7-dihydroxy-4-cyclopentyl-2 (1H) quinazolinone-1-propionic acid is prepared. The method of claim 1, wherein 5,6-dihydroxy-4-methyl-2 (1H) quinazolinone-1-propionic acid monohydroiodide is prepared. The method of claim 1, wherein 6,7-dihydroxy-2 (1H) quinazolinone-1- (2'-methyl) propionic acid is prepared. The method of claim 1, wherein the 6,7-dihydroxy-4-methyl-2 (1H) quinazolinone-1-propionic acid N-methylglucamine salt is prepared. The process of claim 1, wherein the 6,7-dihydroxy-4-methyl-2 (1H) quinazolinone-1-propionic acid mono (2-methyl-2amino-1,3-propanediol) salt is prepared. The process of claim 1, wherein the 6,7-dihydroxy-4-methyl-2 (1H) quinazolinone-1-propionic acid mono (1-amino-2,3-propanediol) salt is prepared. The method of claim 1, wherein the 6,7-dihydroxy-4-methyl-2 (1H) quinazolinone-1-propionic acid monoarginine salt is prepared. The method of claim 1, wherein 5,6-dihydroxy2 (1H) quinazolinone-1-propionic acid is prepared. The process for producing 6,7-dihydroxy-4-methyl-2 (1H) quinazolinone-1-propionate monoethylamine salt according to claim 1. The method of claim 1, wherein the 6,7-dihydroxy-4-methyl-2 (1H) quinazolinone-1-propionic acid piperazine salt is prepared. The process according to claim 1, wherein the 6,7-dihydroxy-4-methyl-2 (1H) quinazolinone-1-propionic acid N-methylpiperazin salt is prepared. The method of claim 1, wherein the 6,7-dihydroxy-4-methyl-2 (1H) quinazolinone-1-propionic acid morpholine salt is prepared. The method according to claim 1 or 7, wherein the compound of formula (1) is 5,6-dimethoxy-4-methyl-2 (1H) quinazolinone. The method according to claim 1 or 7, wherein the compound of formula (1) is 5,6-dimethoxy-2 (1H) quinazolinone. ※ Note: The disclosure is based on the initial application.