Malonic acid dinitrile

Trimethoprim has also been synthesized by condensing 3,4,5-trimethoxybenzaldehyde with malonic acid dinitrile in a Knoevenagel reaction, which forms the derivative (33.1.53), which is partially reduced to the enamine (33.1.54) by hydrogen using a palladium on carbon catalyst, which upon being reacted with guanidine is transformed into trimethoprim [52,53]. 

Patent Method for Producing Alkoxy Malonic Acid Dinitriles... 

Dihydrofuran derivatives are formed from the reaction of a-nitrooxiranes and malonic acid dinitrile (Eq. 198). ... 

Biphenyl, perchloro 8.8 Malonic acid dinitrile (malononitrile) 15.1... 

Malonic acid dinitrile Malonic dinitrile. See Malononitrile... 

Pudovik, A.N., Zimin, M.G., and Evdokimova, V.V., Reactions of a-keto phosphonates with the cyanoacetic ester and dinitrile of malonic acid, Zh. Obshch. Khim., 42, 1489, 1972 J. Gen. Chem. USSR (Engl. Transl.), 42, 1481, 1972. 

The acid, referred to as tetra acid , is prepared as follows In a Friedel-Crafts reaction, acenaphthene 72 is reacted with malonic dinitrile and aluminum chloride. The resulting condensation product 75 is oxidized with sodium chlorate/hy-drochloric acid to form the dichloroacenaphthindandione 76. Oxidation with sodium hypochlorite solution/sodium permanganate affords naphthalene tetracar-boxylic acid 68, mostly existing as the monoanhydride 68a. The dianhydride, on the other hand, evolves only after drying at approx. 150°C. 

Compound 259 (R = aryl) also reacts with malonic dinitrile, without the addition of special bases, to form the 1,4-dithiafulvene (304).151 Campaigne et a/.153l,b,d successfully carried out similar condensations in boiling glacial acetic acid/pyridine.172... 

Fairly high yields of coumarins are obtainable by irradiation for 4-6 h of methoxycinnamic acids in acetonitrile-water saturated with oxygen and containing naphthalene-1,4-dinitrile. Further routes to the flavone ring system continue to appear. Flavone-3-carboxylic acids are ao ssible from fi-phenoxybenzylidenemalonic acids and either sulphuric acid or trifluoroacetic acid-trifluoroacetic anhydride. Attempts to cyclize the malonic esters were less... 

The chemistry of selenazoles is reviewed in a book <04MI777>. Addition of malonic dinitrile with phosphorus pentaselenide in aqueous ethanol affords selenomalonic diamide 282, which undergoes double cyclization with phenacyl bromide to furnish bis(selenazole) 283 <04S875>. 2-Acyl-l,3-selenazoles 287 are prepared in two steps from bromomethyl ketones 284 and selenoamides 285. A facile preparation of l,3-selenazole-5-carboxylic acids 289 is based on the cyclization of selenazadienes 288 with chloroacetyl chloride <048233>. 

MALONIC DINITRILE (109-77-3) Combustible solid. Dust or powder forms explosive mixture with air (flash point 234°F/122°C cc). Incompatible with sulfuric acid. May polymerize violently on contact with alkalis or temperatures above 160°F/71°C. 

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