Cyanoacetic acid hydrazide

Cyanoacetic acid hydrazide [140-87-4] M 99.1, m 114.5-115°. Crystd from EtOH. 

Reaction of 91 and 92 with 88 furnishes the arylidene products 89 [81S635 84ZN(B)824 87IJC(B)216], whereas the condensation of 92a with cyanoacetic acid hydrazide yields the parent bicyclic product 93 (84JHCI885). Arylidene product 89 is presumed to have been obtained via the intermediate 5-benzylidene derivative of 91 and 92 formed by the addition of the active methylene in 91 and 92 to the activated double bond of benzylidene malononitrile with concomitant elimination of malononi-trile, which subsequently adds to the activated double bond of the interme-... 

Utilities of some carbon nucleophiles in heterocyclic s5mthesis 07C(X1853. Utility of cyanoacetic acid hydrazide in heterocychc synthesis 06ARK(9)... 

The Gewald synthesis of 2-aminothiophen-3-carboxylic acid derivatives has been extended to cyanoacetic acid hydrazides. In the base-catalysed reaction with cyclohexanone and sulphur, the hydrazides yielded the thienopyrimidone derivative (24), which could be hydrolysed to the 2-aminothiophen-3-carboxylic acid hydrazide (24a). A series of substituted 2-aminothiophen-3-carboxylic esters have been prepared by a... 

Butanedioic acid dihydrazide (succinodihydrazide) (C H qO N ) Hexanedioic acid dihydrazide (adipodihydrazide) (CgH O N ) Cyanoacetic acid hydrazide (CgH ONg)... 

N-[3 -(4-Methy Iphenyl)-1 -phenyl-1 H-pyrazol-4-methylidene] -cyanoacetic acid hydrazide 154 was synthesised in an excellent yield by condensing 3-(4-methylphenyl)- -phenyl-lH-pyrazole-4-carboxaldehyde with cyano-acetic acid hydrazide. This intermediate was converted to the 4-amino-3-aryl-5-[3-(4-methylphenyl)-1 -phenyl-1 H-pyrazol-4-methylidenehydrazinocarbonyl] -thiazole-2(3H)-thiones 155 (Scheme 72), following the method described by Gewald, it involved the reaction of the cyanoacetic acid hydrazide derivative 154 with sulphur and the appropriate aryl isothiocyanate in the presence of triethylamine as a basic catalyst. Cyclisation of 145 to the 3-aryl-6-[3-(4-methylphenyl)-l-phenyl-1 H-pyrazol-4-methylideneamino] -2-thioxo-2,3 -dihydrothiazolo [4,5 -djpyrimidin-7(6H)-ones 156 was achieved by heating the former with a mixture of triethyl orthoformate and acetic anhydride (1 1) [4],... 

Chloro-3,4-dihydronaphthalene-2-yl)methylene]amino -1 -phenyl-2-thioxo-1,6- dihydro[l,3]thiazolo[5,4-d]pyrimidin-7(2H)-one, which considered as a 7-thia analogue of the natural purine bases, adenine and guanine, was prepared in an excellent yield by condensing 189 with cyanoacetic acid hydrazide followed by Gewald reaction, by reaction of 190 with suhar and phenyl isothiocyanate in the presence of triethylamine as a basic catalyst to give 191(Scheme 84). Thiazolo[5,4-d]pyrimidinone derivative 192 was prepared by heating 191 with a mixture of triethylorthoformate and acetic anhydride (1 1) [117],... 

Racemic and optically active hydantoins have been prepared through isocyanate derivatives, starting from chiral disubstituted cyanoacetic acids 71.123 Similarly, N2,N2-disubstituted thiocyanatocarboxylic hydrazides give 3-amino-2-thiohydantoin derivatives 72,124 and l-phenyl-3-aminohydantoin is obtained in excellent yield in the reaction of ethyl N-phenyl-N-carbethoxyglycinate and hydrazine hydrate.123... 

Ref. 11 Zommer S and Szuszkiewicz J. Spectrophotometric investigations of acid-base properties of hydrazides of isonicotinic and cyanoacetic acids. Chemia Analityczna (Warsaw, Poland), 14(5), 1075-1083 (1969) CA 72 89616n. 

Curtius reaction, conversion of a pyridine hydrazide to a pyridine amide, 362 Cyanoacetamide, 602, 620 Cyanoacetic acid, 601 Cycloalkano-2-pyridones, preparation from 2- (2-cymo-ethyl) cycloalkanones, 729 a-Cyano-2-butenolc acids, 601... 

Stepwise Degradation to Amino Adds. There are several approaches to the transformation of a di- or poly-carboxylic acid to an amino acid. The most satisfactory procedure makes use of the ester acids and their salts. They react with hydrazine to form hydrazide acids, which may be degraded through the azide acids to amino acids. From substituted malonic esters a-amino acids are obtained. (For the preparation of a-amino acids from substituted cyanoacetic esters, see p. 359.) Thus, the potassium salt of the monoethyl ester of methylmalonic acid, which is prqjared by half hydroly of the diethyl ester, pves alanine ethyl ester hydrochloride in 67% yield. Many other amino acids have... 

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