Cyanacetamide

A similar procedure was developed in greater detail by Domow and Heiberg. They proceeded from aryl or aralkyl azid and cyanacetamide (176) and the 1-aryl- or l-aralkyl-5-amino-i -triazole-... 

C. Reactions with Enaminocai bonyl Compounds and Cyanacetamide. 197... 

The cyclization of the 1,3-enyne amines with cyanacetamide in the presence of bases (55°C, H2O, 2 h) leads to 3-cyano-6-methyl-2-pyridones (155), yield 77% (69ZOR1179). 

Methyl ethyl ketone Ethyl oxalate Hydrogen chloride Ammonia Cyanacetamid Ethanol ... 

Cyano-4-Carbethoxy-6-Ethyl-2-Pyridone 205 cc of 60% aicohoi, 22 grams of the product just obtained, 11 grams of cyanacetamide and 4.5 cc of piperidine are refiuxed. 19 grams of product having a melting point of 211°C are obtained. 

Methyl-n-propyl ketone Cyanacetamide Phosphorus oxychloride Ammonia Hydrogen sulfide... 

B) 3-Cyano-4-Carbethoxy-6-(n)-Propyl-2-Pyridone The 135 grams of the product just obtained are condensed with 62 grams of cyanacetamide in the presence of 24 cc of piperidine in 1200 cc of 95% alcohol. 64 grams of a product, melting at 152°C, are obtained. 

Dimethyl tubocurarine Iodide Cyanacetamid Ethionamide Protionamide Cyanamide Albendazole Butalamine HCl Cimetide Cyanoacetamide Allopurinol Cyanoacetic acid Aminometradine Amisometradine Cyclopentamine HCl Sulindac... 

The methine type comprises isoindoline derivatives which, like tetrachloro-isoindolinone pigments, have only recently been described. One or usually two equivalents of a compound containing an activated methylene moiety are attached to one equivalent of isoindoline. The list of compounds featuring activated methylene groups includes cyanacetamide or heterocycles such as barbituric acid or tetrahydroquinolinedione. 

Knoevenagel adduct 239 of oxohomophthalimide 240 with malononitrile 27a in reactions with CH-acids behaves ambiguously (82CPB1215). Reactions of 239 with acetylacetone, ethyl esters of acetoacetic and ben-zoylacetic acids, as well as methyl pyruvate led to the formation of the desired spiropyrans 241. However, benzoylacetone, dibenzoylmethane, cyanacetamide, and oxindole always gave the same 242. Authors explain this feature in terms of a retro-cleavage of adducts of Michael product 239... 

Cyanoocetamide, Malonatnide Nitrile or Pro-pionamide Nitrile (called Cyanacetamid,... 

Ethyl oxalate Hydrogen chloride Phosphoric anhydride Cyanacetamide Ammonia... 

As early as 1986, both Wall and coworkers [46] and a Chinese group [47] recognized the potentiality of a Friedlander synthesis approach from 2-aminobenzaldehyde with the synthon 14 and developed an approach to racemic 14, based on the extremely efficient condensation of ethyl acetoacetate with cyanacetamide by Henecka [48], which provides in one step a pyridone intermediate IS with three different sub-... 

Both pyrrole itself, as well as 4,5,6,7-tetrahydroindole underwent N-vinylation with 2-cyano-l-phenylacetylene in DMSO in the presence of KOH, while the treatment of 4,5,6,7-tetrahydroindole with 2-benzoyl-1-phenylacetylene under the same conditions furnished predominantly a C-vinylated product <03S1272>, Several functionalized 3-vinylpyrroles were prepared by reaction of pyrrole-3-carbodithioates with malonitrile, cyanacetamide, or ethyl cyanoacetate induced by KOH in DMSO <03TL3501>. 

Benzofuroxan (5) (X = H) (13.6g, 0.1 mol) and sodium hydroxide (20g, 0.5 mol) are suspended and dissolved respectively in water (100 ml). Then, with ice cooling to maintain the reaction temperature between 10 and 15°C, a stream of cyanacetamide (25.2 g, 0.3 mol) is added over lOmin. After brief concentration the sodium salt of (6) separates as a dense yellow precipitate, which is collected by suction filtration, rcdissolved in water, and acidified with dilute hydrochloric acid to give (6) (X = H, R = CONH2) as pale yellow crystals (15 g, 78%) which decompose violently at 219°C. Similarly prepared are (6) (X, R, yield given) H, CONHMe, 59% H, CONHEt, 72% H, CONH-cyclohexyl, 92% H, CONHPh, 41% 6-Cl, CONH2, 53% 6-Me, CONH2, 32% 6-OMe, CONH2, 37%. 

Cyanessigsaure-ethylestcr Malonsaure-dinitril Nitroessigsaure-ethylesler N-Ethoxycarbonyl-cyanacetamid 2,2-Dimethyl-4,6-dioxo-1,3-dioxan (Meldrum-Saure)... 

Oxobenzopyran-3-carbaldehyde (3-formylchromone) continues to prove a valuable synthetic intermediate. A one-pot synthesis of 4-oxobenzopyran-3-nitriles is based on a Vilsmeier-Haaek synthesis of 4-oxobenzopyran-3-carbaldehyde <04TL847>. 3-Formyl-chromones react with cyanacetamides and other electron-deficient acetic acid amides to give... 

N-(Piperidino)cyanacetamide followed after 2 min. by phenyl isothiocyanate added to a soln. of Na-ethoxide in dry ethanol, heated 2 hrs. on a steam bath. 

The first total synthesis of vitamin Bg was obtained by the condensation of acetylacetone and cyanacetamide. 

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