KR840001175A - Method for preparing [3H] -imidazo [5,1-d] -1,2,3,5-tetrazin-4-one derivative - Google Patents

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Method for preparing [3H] -imidazo [5,1-d] -1,2,3,5-tetrazin-4-one derivative

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Claims (15)

[ 3H ] -imidazo [5,1-d] -1,2,3,5-tetrazine- of Structural Formula (I) by reacting a compound of Structural Formula (II) with an isocyanate of Structural Formula (III) Process for preparing 4-one derivatives. . Wherein R ¹ is unsubstituted or substituted by 1-3 substituents selected from halogen atoms, straight alkoxy, alkylthio, alkylsulfinyl and alkylsulfonyl groups having 1-4 carbon atoms and optionally substituted phenyl groups; A -6 straight or branched chain alkyl, alkenyl or alkynyl group and a C3-8 cycloalkyl group; R ² is a carbamoyl group in which one or two atom groups selected from straight and branched chain alkyl and alkenyl groups having 1 to 4 carbon atoms and cycloalkyl groups having 3 to 8 carbon atoms are bonded to nitrogen, and R ³ is a halogen atom, 1 carbon atom Straight or branched chain alkyl of 1 to 6 carbon atoms, unsubstituted or substituted by a substituent of 1-3 selected from a straight or branched alkoxy, alkylthio, alkylsulfinyl and alkylsulfonyl group optionally substituted with -4; A kenyl or alkynyl group or cycloalkyl having 3-8 carbon atoms. [ 3H ] -imidazo [5,1-d] -1,2,3,5 of formula (I) by reacting a compound of formula (IV) or an alkali metal salt thereof with a compound of formula (V) To prepare a tetrazin-4-one derivative. R ³ XV Wherein R ¹ , R ² , R ³ are as defined above and X is the acid residue of the reactive ester. The method for producing the compound of formula (I) according to claim 2, wherein X is a halogen atom, a methoxysulfonyloxy group, a methanesulfonyloxy group, or a toluene- P -sulfonyloxy group. After reacting a compound of formula (II) with a compound of formula (VI), R ¹ represents hydrogen by substituting a hydrogen atom by a known method for protecting groups in the compound of formula (VII) obtained when R ⁴ is a protecting group [3H] -imidazo- [5,1-d] -1,2,3,5-tetrazin-4-one derivative of the formula (I) wherein R ² is an atom and an alkali metal salt thereof How to manufacture. Wherein R ² is as in Claim 1, R ⁴ is an alkali metal atom or protecting group (eg benzyl or P-methoxybenzyl group), and R ⁵ is a protecting group such as benzyl or P-methoxybenzyl group . The compound according to claim 1, 2 or 3, wherein R ¹ is an alkyl, alkenyl or alkynyl group substituted by 1-3 optionally substituted phenyl groups, and the optional substituent in the phenyl radical has 1 to 4 carbon atoms. Method for producing a tetrazine derivative of the formula characterized in that it is selected from an alkoxy group, an alkyl group and a nitro group. According to claim 1, 2 or 3 wherein R ¹ is selected, an alkoxy group or one or a halogen atom having an optionally substituted phenyl group, having 1 to 4 carbons substituted by alkoxy groups of 1 or 2 having a carbon number of 1 to 4 substituted And a straight or branched chain alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or a cyclohexyl group. 7. A process according to claim 6, wherein the halogen atoms are chlorine, fluorine and or bromine, the alkoxy group is methoxy and the alkenyl group is allyl. The method for producing the tetrazine derivative of the above formula (I) according to claim 1, 2 or 3, wherein R ¹ is a linear or branched alkyl group having 1 to 6 carbon atoms which is substituted or unsubstituted with a halogen atom. . The method for preparing the tetrazine derivative of the above formula (I) according to claim 1, 2 or 3, wherein R ¹ is an alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with a halogen atom. The process for producing the tetrazine derivative of formula (I) according to claim 1, 2 or 3, wherein R ¹ is a methyl group or a 2-haloalkyl group. The process for producing the tetrazine derivative of formula (I) according to claim 10, wherein the halogen atom in the alkyl group is chlorine or fluorine. The process for producing the tetrazine derivative of formula (I) according to claim 1, 2 or 3, wherein R ¹ is a 2-fluoroethyl or 2-chloroethyl group. The process for producing the tetrazine derivative of formula (I) according to claim 1, 2 or 3, wherein R ¹ is a benzyl or P -methoxybenzyl group. The monoalkylcarbamoyl group according to any one of claims 1 to 13, wherein R ² in the tetrazine product of formula (I) specified in claim 1 has a carbamoyl group, an alkyl group having 1 to 4 carbon atoms, or an egg. A method for producing a tetrazine derivative, wherein the kenyl group is a monoalkenylcarbamoyl group having 1 to 4 carbon atoms. The structural formula (I) according to claim 1, 2 or 3, wherein R ¹ is a linear or branched alkyl, alkenyl or alkynyl group having 1 to 6 carbon atoms which is optionally substituted with a halogen atom of 1-3. To prepare a tetrazine derivative. ※ Note: The disclosure is based on the initial application.