74119-79-2

Upstream product

• 19176-80-8 1,1-Bis(dimethylamino)-3,3-dimethoxy-3-phenyl-1-propen 
• 124-42-5 acetamidine hydrochloride 
• 19176-75-1 3,3,3-tris(dimethylamino)-1-phenyl-prop-2-yne 
• 19176-76-2 <2,2-Bis(dimethylamino)vinyl>keton 

Relevant academic research and scientific papers

Orthoamides, LXV [1]. Condensation reactions of amidines, guanidines, hydrazine and hydrazine derivatives with orthoamides of alkyne carboxylic acids

The orthoamide derivatives 4 react with amidines 10 and guanidines 11 to give 4-dimethylaminopyrimidines 12. The 3-dimethylamino-pyrazoles 13a - c can be prepared from orthoamides 4 and hydrazine. The hydrazine derivative 14, whose constitution was established by crystal structure analysis, is obtained in low yield when hydrazine is added dropwise to a boiling solution of 4d in THF. Methyl- and Phenylhydrazine, undergo reaction with the orthoamides 4a, c yielding mixtures of the isomeric pyrazoles 19 and 20. The reaction of 4c with acylhydrazines 21a - e affords the pyrazole 13b. The pyrazole 26 is produced in the reaction of 4a and acet-hydrazide according to this scheme, whereas 4a reacts with aromatic acid hydrazides 21c - e to give condensation products, which are presumably amidrazones 28. The 4,5-diaza-octatetraene derivative 30 results from the reaction of 4c with p-toluenesulfonylhydrazide. Ketene aminals 34a-c are the products of the reaction of the orthoamides 4b - d with 4,4-dimethylthiosemicarbazide 34, which cyclize on heating to give high-melting pyrazolethiones 35a - c. According to the crystal structure analysis of 35c the compounds have zwitterionic character and are associated via hydrogen bridges in the solid state.

Orthoamides, XXXIV.-Syntheses with Vinylidenediamines

Vinylidenediamines 2a,c have been prepared from 1-ethoxyvinylamine 4 and dimethylamine or pyrrolidine, respectively.Heating of 2a and formamidinium acetate affords 4-amino-5-pyrimidinecarbonitrile (7b).Acylation of 2a with acid chlorides or acid anhydride