malonic acid

Malonic acid

Malonsäure

malonic acid

Malonsäure

Malonic acid derivatives.

Malonsäurederivate.

Malonic Acid

Cyclobutan

Methyl malonic acid

Methylmalonsäure

The novel thiazolopyrimidines of the formula (II) are obtained when iminothiazolidines of the general formula (IV) ##STR166## in which R.sup.1 and R.sup.2 have the abovementioned meanings, are reacted with malonic acid esters, such as, for example, dimethyl malonate or diethyl malonate, in the presence of metals, metal hydroxides and/or metal alkoxides, such as, for example, sodium, sodium hydroxide, sodium methoxide and/or sodium ethoxide, in the presence of diluents, such as, for example, methanol and/or ethanol, at temperatures between 10 C. and 100 In formula (IV), R.sup.1 and R.sup.2 preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I), according to the invention, as being preferred, or particularly preferred, for R.sup.1 and R.sup.2.

Man erhält die neuen Thiazolopyrimidine der Formel (II), wenn man Iminothiazolidine der allgemeinen Formel (IV) in welcher R¹ und R² die oben angegebenen Bedeutungen haben, mit Malonsäureestern, wie z. B. Malonsäuredimethylester oder -diethylester, in Gegenwart von Metallen, Metall­ hydroxiden und/oder Metallalkoholaten, wie z. B. Natri­ um, Natriumhydroxid, Natrium-methylat und/oder Natrium­ ethylat, in Gegenwart von Verdünnungsmitteln, wie z. B. Methanol und/oder Ethanol, bei Temperaturen zwischen 10 °C und 100 °C umsetzt. In Formel (IV) haben R¹ und R² vorzugsweise bzw. insbe­ sondere diejenigen Bedeutungen, die bereits oben im Zu­ sammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) vorzugsweise bzw. als ins­ besondere bevorzugt für R¹ und R² angegeben wurden.

Process according to Claim 5, wherein the complexing agent is selected from: trisodium citrate; disodium ethylenediaminetetraacetate; disodium oxalate; tartaric acid; malonic acid; maleic acid; citric acid; oxalic acid; salicylic acid; glycine; glutamic acid; aspartic acid; alpha-amino-n-butyric acid; methionine serine; threonine; triethylenetetramine; diethylenetetramine; tris(2-aminoethyl )amine, and ethylenediamine.

Verfahren nach Anspruch 5, worin das Komplexierungsmittel unter: Trinatriumcitrat, Dinatriumethylendiamintetraacetat, Dinatriumoxalat, Weinsäure, Malonsäure, Maleinsäure, Zitronensäure, Oxalsäure, Saicylsäure, Glycin, Glutaminsäure, Asparaginsäure, alpha-Amino-n-buttersäure, Methionin, Serin, Threonin, Triethylentetramin, Diethylentetramin, tris(2-Aminoethyl)amin und Ethylendiamin ausgewählt ist.

The compound of any one of claims 1-4, wherein X=H and Y=H. A compound selected from the group consisting of: (1S,2S)-2-methoxy-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(ethoxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(isopropoxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(1-propenyloxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(2-trimethylsilyl-ethoxy)1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-benzyloxy-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(4-methoxybenzyloxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(2,2,2-trifluoro-ethoxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-6,7-difluoro-2-methoxy-1,2-dihydro-naphthalen-1-ol; (1S,2S)-6-methoxy-5,6-dihydro-naphthol[2,3-d][1,3]dioxol-5-ol; (1S,2S)-6,7-dibromo-2-methoxy-5,8-dimethyl-1,2-dihydro-naphthalen-1-ol; (1R*,2R*)-acetic acid 1-hydroxy-1,2-dihydro-naphthalen-2-yl-ester; (1R*,2R*)-propionic acid 1-hydroxy-1,2-dihydro-naphthalen-2-yl-ester; (1R,2R)-benzoic acid 1-hydroxy-1,2-dihydro-naphthalen-2-yl-ester; (1R*,2R*)-formic acid 1-hydroxy-1,2-dihydro-naphthalen-2-yl-ester; (1R*,2R*)-2-methyl acrylic acid 1-hydroxy-1,2-dihydro-naphthalen-2-yl-ester; (1R*,2R*)-malonic acid ethyl ester (1-hydroxy-1,2-dihydro-naphthalen-2-yl) ester; (1R*,2R*)-malonic acid (1-tert-butylbimethylsiloxy-1,2-dihydro-naphthalen-2-yl) ethyl ester; (1S*,2S*)(4-tert-butyldimethylsiloxy-1,4-dihydro-naphthalen-2-yl) acetic acid ethyl ester; (1R,2R)-2-(1-hydroxy-1,2-dihydro-naphthalen-2-yl)-isoindole-1,3-dione; (1S,2S)-N-(1-hydroxy-1,2-dihydro-naphthalen-2-yl)-benzene sulfonamide; (1R*,2R*)-2-pyrrolidin-1-yl-1,2-dihydro-naphthalen-1-ol; (1R*,2R*)-2-piperidin-1-yl-1,2-dihydro-naphthalen-1-ol; (1R,2R)-2-(3,4-dihydro-2H-quinolin-1-yl)-1,2-dihydro-naphthalen-1-ol; (1R,2R)-2-(methyl-phenyl-amino)-1,2-dihydro-naphthalen-1-ol; (1R*,2R*)-2-benzylamino-1,2-dihydro-naphthalen-1-ol; (1R*,2R*)-2-(4-methoxy-benzylamino)-1,2-dihydro-naphthalen-1-ol; (1R,2R)-2-indol-1-yl-1,2-dihydro-naphthalen-1-ol; (1S*,2R*)-2-(hydroxy-1,2-dihydro-naphthalen-2-yl)malonic acid dimethyl ester; (1S,2S)-2-phenoxy-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(4-nitrophenoxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(4-cyanophenoxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(4-acylphenoxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(4-trifluoromethylphenoxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(4-fluorophenoxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(4-chlorophenoxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(4-iodophenoxy)-1,2-dihydro-naphthalen-1-ol; (1R,2R)-2-(4-bromo-phenoxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(4-methylphenoxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(4-methoxyphenoxy)-1,2-dihydro-naphthalen-1-ol; (1S,2S)-2-(2-bromophenoxy)-1,2-dihydro-naphthalen-1-ol; 4-methyl-N-[(1R, 2S)-2-( 1-piperidinyl)-1,2-dihydro-1-naphthalenyl]benzenesulfonamide; N-[(1R,2S)-2-(3,4-dihydro-1(2H)-quinolinyl)-1,2-dihydro-1-naphthalenyl]-4-methylbenzenesulfonamide; N-[(1R,2S)-2-(3,4-dihydro-2(1H-isoquinolinyl)-1,2-dihydro-1-naphthalenyl]-4-methylbenzenesulfonamide; N-[(1R,2S)-2-(1H-indol-1-yl)-1,2-dihydro-1-naphthalenyl]-4-methylbenzenesulfonmidde; (1R,2S)-2-methoxy-N-phenyl- 1,2-dihydro-1 -naphthalenamine; tert-butyl (1R,2S)-2-methoxy- 1,2-dihydro- 1 -naphthalenylcarbamate; N-[(1R,2S)-2-methoxy-1,2-dihydro-1-naphthalenyl]-2-(trimethylsilyl)ethanesulfonamide; N,4-dimethyl-N-[(1R,2S)-2-(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthalenyl]-benzenesulfonamide; N,4-dimethyl-N-[ (1R,2S)-2-(1-pyrrolidinyl)-1,2-dihydro-1-naphthalenyl]-benzenesulfonamide; N-hydroxy-4-({methyl[(1R,2S)-2-(1-pyrrolidinyl)-1,2-dihydro-1-naphthalenyllamino}sulfonyl) -N-oxobenzenaminium; N-methyl-4-nitro-N-[( 1R,2S)-2-(1-pyrrolidinyl)-1,2-dihydro-1-naphthalenyl]-benzenesulfonamide; (1R,2S)-N-methyl-2-(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthalenamine; N-[( 1R, 2S)-2-methoxy-1,2,3,4-tetrahydro-1-naphthalenyl]-4-methylbenzenesulfonamide; N-[(1R,2S)-2-methoxy-1,2,3,4-tetrahydro-1-naphthalenyl]-4-methylbenzenesulfonamide; 4-methyl-N-[(1R,2S)-2-phenoxy-1,2,3,4-tetrahydro-1-naphthalenyl]benzenesulfonamide; (1R,2S)-1-{[(4-methylphenyl)sulfonyl]amino)-1,2,3,4-tetrahydro-2-naphthalenyl acetate; (1R,2S)-1-{[(4-methylphenyl)sulfonyl]amino}-1,2-dihydro-2-naphthalenyl benzoate; (1R,2S)-1-{[(4-methylphenyl)sulfonyl]amino1,2-dihydro-2-naphthalenyl pivalate; N-[(1R,2S)-2-methoxy-1,2-dihydro-1-naphthalenyl]-2-(trimethylsilyl)ethanesulfonamide; tert-butyl (1R,2S)-2-methoxy-1,2-dihydro-1-naphthalenylcarbamate; and 4-nitro-N-[(1R,2S)-2-( 1-pyrrolidinyl)-1,2-dihydro-1-naphthalenyl]benzenesulfonamide.

Verbindung nach einem der Ansprüche 1-4, wobei X=H und Y=H. Verbindung die aus der folgenden Gruppe stammt: (1S,2S)-2-Methoxy-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(Ethoxy)-1,2-dihydronaphthalen-1-ol;/ (1S,2S)-2-(Isopropoxy)-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(Propenyloxy)-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(2-Trimethylsilyl-ethoxy)-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-Benzyloxy-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-4-Methoxybenzyloxy)-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(2,2,2-Trifluorethoxy)-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(2,2,2-Trifluor-1-trifluormethylethoxy)-1,2-dihydronaphthalen-1-ol; (1S,2S)-6,7-Difluor-2-methoxy-1,2-dihydronaphthalen-1-ol; (1S,2S)-6-Methoxy-5,6-dihydronaphthol[2,3-d][1,3]-dioxol-5-ol; (1S,2S)-6,7-Dibrom-2-methoxy-5,8-dimethyl-1,2-dihydronaphthalen-1-ol; (1S*,2S*)-Essigsäure-1-hydroxy-1,2-dihydronaphthalen-2-yl-ester; (1S*,2S*)-Propionsäure-1-hydroxy-1,2-dihydronaphthalen-2-yl-ester; (1R,2R)-Benzoesäure-1-hydroxy-1,2-dihydronaphthalen-2-yl-ester; (1R,2R)-Ameisensäure-1-hydroxy-1,2-dihydronaphthalen-2-yl-ester; (1R,2R)-2-Methylacrylsäure-1-hydroxy-1,2-dihydronaphthalen-2-yl-ester; (1R,2R)-Malonsäureethylester-(1-hydroxy-1,2-dihydronaphthalen-2-yl)ester; (1R,2R)-Malonsäure-(1-tert.-butylbimethylsiloxy-1,2-dihydronaphthalen-2-yl)ethylester; (1S*,2S*)-4-tert.-Butyldimethylsiloxy-1,4-dihydronaphthalen-2-yl)-essigsäureethylester; (1R,2R)-2-(1-Hydroxy-1,2-dihydronaphthalen-2-yl)-isoindol-1,3-dion; (1S,2S)-N-(1-Hydroxy-1,2-dihydronaphthalen-2-yl)-benzolsulfonamid; (1R*,2R*)-2-Pyrrolidin-1-yl-1,2-dihydronaphthalen-1-ol; (1R*,2R*)-2-Piperidin-1-yl-1,2-dihydronaphthalen-1-ol; (1R,2R)-2-(3,4-Dihydro-2H-chinolin-1-yl)-1,2-dihydronaphthalen-1-ol; (1R,2R)-2-(Methylphenylamino)-1,2-dihydronaphthalen-1-ol; (1R*,2R*)-2-Benzylamino-1,2-dihydronaphthalen-1-ol; (1R*,2R*)-2-(4-Methoxybenzylamino-1,2-dihydronaphthalen-1-ol; (1R,2R)-2-Indol-1-yl-1,2-dihydronaphthalen-1-ol; (1S*,2R*)-2-(Hydroxy-1,2-dihydronaphthalen-2-yl)-malonsäuredimethylester; (1S,2S)-2-Phenoxy-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(4-Nitrophenoxy-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(4-Cyanophenoxy-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(4-Acylphenoxy-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(4-Trifluormethylphenoxy-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(4-Fluorphenoxy-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(4-Chlorphenoxy-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(4-Iodphenoxy-1,2-dihydronaphthalen-1-ol; (1R,2R)-2-(4-Bromphenoxy-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(4-Methylphenoxy-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(4-Methoxyphenoxy-1,2-dihydronaphthalen-1-ol; (1S,2S)-2-(2-Bromphenoxy-1,2-dihydronaphthalen-1-ol; 4-Methyl-N-[(1R,2S)-2-(1-piperidinyl)-1,2-dihydro-1-naphthalenyl]benzolsulfonamid; N-[(1R,2S)-2-(3,4-Dihydro-1(2H)-chinolinyl)-1,2-dihydro-1-naphthalenyl]-4-methylbenzolsulfonamid; N-[(1R,2S)-2-(3,4-Dihydro-2(1H)-isochinolinyl)-1,2-dihydro-1-naphthalenyl]-4-methylbenzolsulfonamid; N-[(1R,2S)-2-(1H-indol-1-yl)-1,2-dihydro-1-naphthalenyl]-4-methylbenzolsulfonamid; (1R,2S)-2-Methoxy-N-phenyl-1,2-dihydro-1-napthalenamin; tert.-Butyl(1R,2S)-2-methoxy-1,2-dihydro-1-naphthalencarbamat; N-[(1R,2S)-2-Methoxy-1,2-dihydro-1-naphthalenyl]-2-(trimethylsilyl)ethansulfonamid; N,4-Dimethyl-N-[(1R,2S)-2-(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthalenyl]benzolsulfonamid; N,4-Dimethyl-N-[(1R,2S)-2-(1-pyrrolidinyl)-1,2-dihydro-1-naphthalenyl]benzolsulfonamid; N-Hydroxy-4-({methyl[(1R,2S)-2-(1-pyrrolidinyl)-1,2-dihydro-1-naphthalenylamino)sulfonyl)-N-oxobenzolaminium; N-Methyl-4-nitro-N-[(1R,2S)-2-(1-pyrrolidinyl)-1,2-dihydro-1-naphthalenyl]benzolsulfonamid; (1R,2S)-N-Methyl-2-(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthalenamin; N-[(1R,2S)-2-Methoxy-1,2,3,4-tetrahydro-1-naphthalenyl]-4-methylbenzolsulfonamid; N-[(1R,2S)-2-Methoxy-1,2,3,4-tetrahydro-1-naphthalenyl]-4-methylbenzolsulfonamid; 4-Methyl-N-[(1R,2S)-2-phenoxy-1,2,3,4-tetrahydro-1-naphthalenyl]-4-methylbenzolsulfonamid; (1R,2S)-1-{[(4-Methylphenyl)sulfonyl]amino)-1,2,3,4-tetrahydro-1-naphthalenylacetat; (1R,2S)-1-{[(4-Methylphenyl)sulfonyl]amino)-1,2-dihydro-1-naphthalenylbenzoat; (1R,2S)-1-{[(4-Methylphenyl)sulfonyl]amino)-1,2-dihydro-2-naphthalenylpivalat; N-[(1R,2S)-2-Methoxy-1,2-dihydro-1-naphthalenyl]-2-(trimethylsilyl)ethansulfonamid; tert.-Butyl(1R,2S)-2-methoxy-1,2-dihydro-1-naphthalenylcarbamat; und 4-Nitro-N-[(1R,2S)-2-(1-pyrrolidinyl)-1,2-dihydro-1-naphthalenyl]benzolsulfonamid.