Guanidine, Cyano

CYANO(METHYLMERCURI)GUANIDINE GUANIDINE, CYANO-, METHYLMERCURY deriv. MEMA METHYLMERCURIC CYANOGUANIDINE xMETHTL-MERCURIC DICYANDIAMIDE METHYLMERCURY DICYANDIAMIDE METHYLMERKURIDIKYANDI-AMID MMD MORSODREN MORTON EP-227 O MORTON SOIL DRENCH MORTON SOIDDRENCH-C... 

Synonyms Cetramin Dicyandiamide-formaldehyde adduct Dicyandiamide-formaldehyde polymer Guanidine, cyano-, polymer with formaldehyde Formula (C2H4N4 CH20)x Toxicology LD50 (oral, rat) 1750 mg/kg mod. toxic by ing. irritating to eyes and skin Hazardous Decomp. Prods. Heated to decomp., emits toxic fumes of NOx and CN ... 

Two interesting syntheses of the base followed in 1956 the first involves a Principal Synthesis from ethyl 2-cyano-2-(tetrahydropyran-2 -yloxy)acetate and guanidine to give the tetrahydropyranyloxypyrimrdine (949) which undergoes gentle acidic hydrolysis to... 

Cyclocondensation of 3-cyano-2-methylthio-4//-pyrido[l, 2-u]pyrimidin-4-ones and ethyl mercaptoacetate in boiling EtOH in the presence of NaOEt afforded 4//-pyrido[l,2-u]thieno[2,3-r/ pyrimidin-4-ones 210 (00HC571). 2-Methylthio-4-oxo-4//-pyrido[l,2-u]pyrimidine-3-carboxylates 211 and mercaptoacetates afforded tricyclic derivatives 212 (93MIP1). Cyclocondensation of 2-methylthio-4-oxo-4//-pyrido[l, 2-u]pyrimidin-3-car-bonitriles 213 with H2NNH2 H2O and with guanidine HCl afforded tricyclic derivatives 214 and 215, respectively (96FES781). 

Chemical Name N-cyano-N -methyl,N"-[2-[ [(5-methyl-1 H-imidazol-4-yl)methyl] thio] ethyl] guanidine... 

More recently, ammonium sulphonates have proved excellent reagents for converting cyano- into amidino-groups (488). Applied to the present case, the use of ammonium sulphonates at 140—160° is particularly useful in the production of 1-arylbiguanides (44, 488, 613, 614). As expected, action of two moles of ammonium sulphonates results in guanidines. 

The reactions with the aminocyanofiirans produced an unexpected result, however, as illustrated by the following example. 2-Amino-3-cyano-4-methylfuran was added to a solution of guanidine free base in ethanol, and the mixture was heated under reflux for 24 hours. Standard work-up gave the pyrrolo[2,3-d]pyrimidine 3 in 67% yield, and not the expected furo[2,3-[Pg.146]

An unequivocal synthesis of (637), protected as its A-2 -acetyl derivative (643), was successfully accomplished as shown in Scheme 3.140 [40]. Pyruval-dehyde dimethylacetal was first converted into its enamine (108). Condensation of (108) with the O-tosyl derivative of oximinomalononitrile gave the azadiene (638), which was converted to 2-amino-3-cyano-6-dimethoxymethyl-pyrazine (639) with ammonia. This latter compound was condensed with guanidine and the product (640) hydrolyzed first with base (to remove the 4-amino group) and then with acid to give pterin-7-carboxaldehyde (641). Acetylation of (641) followed by condensation with di-t-butyl p-aminobenzoyl-glutamate (235), reduction and hydrolysis gave (643). 

The 7-isomer of 10-thiaAP (653) was prepared by taking advantage of the Taylor unequivocal synthesis of 2-amino-3-cyano-6-chloromethylpyrazine (645). Thus, condensation of the latter with the anion of diethyl p-mercaptoben-zoylglutamate (40) [53], followed by guanidine cyclization and saponification, gave (653) (Scheme 3.143) [263]. 

---