IL38412A - Alpha-cyano-3,4,5-trialkoxycinnamic acid derivatives - Google Patents

Abstract

Title cpds. are of formula: (where R1 and R2 are each H, halogen, lower alkyl or alkoxy; R3 and R4 are each lower alkoxy; Y is OH or amino gp. opt. alkyl-substd., the broken alpha,beta-line may denote a double bond; if the double bond is absent, the alpha and beta C atoms carry H atoms instead; with the proviso that in the presence of a double bond R1 is not H, R2-4 are not methoxy gps., and Y is not OH) and they are produced by reacting the corresp. benzaldehyde with NC-CH2COY in the presence of a basic condensation catalyst, and opt. hydrogenating the product. [DE2258239A1]

Description

acid derivatives Plantex cinnamic present invention relates to and of general formula I in which and or different stands Tor and stand for the satae or different lover alkoxy Y stands for a or an unsubstituted or amino group and the dotted line designates either an additional bond or hydrogen atoms at the carbon ding The compounds of formula I are valuable intermediates in a process for the preparation of certain pyrimidines vhich in turn are easily transformed to pharmaceutically valuable as described in Israel Patent Specification The present invention consists also in a process for the preparation of compounds of general formula I an aldehyde of general formula II in vhich and have the same meaning as above is reacted in the presence of a suitable basic catalyst vith a compound of eneral formula III which Y has the same meaning as above to yield a compound of general formula in and have the same meaning as if the compound of general formula IV is ticaljy with a suitable in a suitable inert solvent to yield the desired compound of general formula V in which She basic caalys used in the reaction step is preferably a secondary amine a or sodium or preferably potassium ste in an inert solvent such tetrohydrofuranj Said step is preferably performed at between temperatures are indicated herein in degrees As catalyst the step there may be or platinized As suitable solvents there may be mentioned ethyl The present invention consists also in a process for preparation of pyriaidines in which a compound of general formula V without a solvent or in the presence of a suitable reacted with guanidine to yield a compound of general formula VI in which and have the same meaning as The with guanidine when being performed in an inert is performed preferably in an alcohol such as The invention will now be illustrated with reference to the following examples without being limited by Example 1 A mixture of 100 g of and g of cyanoacetic acid in 1 of water containing 21 g of sodium hydroxide was stirred for 2 hours at The clear solution obtained was 120 cc of 5N hydrochloric acid were added and after additional cooling the precipitate was filtered off and washed with 200 of The crude material was dried at and used in the hydrogenation step without It melted at The yield of acid was 126 g Example 2 100 g of obtained in She mixture was hydrogenated at atmospheric pressure until the absorption of hydrogen had The catalyst removed and 175 cc of hydrochloric acid were She precipitate filtered washed 200 cc of water and dried vacuo at for 10 hours to yield g of acid A pure recrystaHized from chloroform melted at Example 100 g of and 44 g of acetamide dissolved in 300 of dry pyridine at To this solution 10 oc of piporidine added and the mixture was heated at the above temperature with stirring for 2 The reaction mixture was cooled at room filtered off and the tate was washed on the filter with 50 cc of cold product was dried at to yield of This product wasused for the hydrogenation step without further A recrystaHiaed from melted at Example 4 100 g of obtained in example 3 were dissolved in of a mixture of and g of of charcoal were The mixture was at atmospheric pressure until the absorption of hydrogen had catalyst was removed and the solvent was evaporated under residue was crystallized from ethyl acetate to after drying at for 6 g of To a solution of 23 g of sodium in 90 g of guanidine carbonate was added and the mixture vas stirred for 13 minutes at She precipitated carbonate vas filtered off with over and the solids washed 200 co of To this guanidine solution in methanol vere added 132 g prepared as described in example solution vas for 6 hours and the methanol was distilled off in residue vas dissolved in 300 of water and the product by the addition of hydrochloric acid to pH After allowin to cool at for 2 hours the white solid filtered off and washed with 40 cc of She product was dried at for 12 hours to of colourless e 100g A mixture 60 g of freshly guanidine was heated at for 1 hour with occasional reaction mixture was in 75 cc of hot water and the solution was She product was precipitated by aiding to the clear hydrochloric to pH After allowing to cool at for 4 hours the solid was filtered off and washed with 30 cc of She product was at for 12 hours to obtain g Of a compound which was identical with the compound obtained in example insufficientOCRQuality

Claims (1)

1. 6 Claims cinnamic acids and amides of general ormula I in which stands for stands for lower and stand for the same or different lower alkoxy Y stands for a hydroxy or an unsubstituted or amino group and the dotted line designates either an additional bond or hydrogen atoms at the carbon excluding A process for the preparation of compounds of general formula I as defined in Claim 1 an aldehyde of general formula II in which and have the same meaning as in Claim 1 is reacted in the presence of a suitable basic catalyst with a which Y has sane moaning as in 1 to yield a compound of general I in which and Y have the same meaning as in Claim if the compound of general formula IV is tically with a suitable catalyst in a suitable inert solvent to yield the desired of general formula V in which Y have the same as in Claim A process according to 5 wherein the basic catalyst of reaction step a secondary or potassium hydroxide or a A process according to or wherein reaction step is performed in an inert an an piperidine or A process according to any of Claims 5 to 7 wherein the hydrogenation catalyst is charcoal and the inert A process for preparation of of general formula as defined in Claim substantially as hereinbefore described with reference to the Examples 1 to Compounds of general formula as defined in Claim 1 whenever prepared by the process according to any of 5 to A process for the preparation of in which and Y have the same as in Claim 1 without a solvent or in the presence of suitable reacted to yield a compound of general in which have the same as in Claim A process according to Claim wherein the reaction la performed in an alcoholic A process for the preparation pyrimidines of general VI as defined in stantially as hereinbefore described with reference to examples of general formula VI 11 whenever prepared by the process according o any of claims to the Applicante Yitzhak Hess insufficientOCRQuality