41270-89-7

Upstream product

• 127-19-5 N,N-dimethyl acetamide 
• 100-47-0 benzonitrile 
• 58979-04-7 C₁₈H₂₀N₂ 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 19176-75-1 3,3,3-tris(dimethylamino)-1-phenyl-prop-2-yne 
• 1670-14-0 benzamidine monohydrochloride 

Relevant academic research and scientific papers

2-Aza-1,3-dienes with electron-releasing substituents at the 1,3 positions. Reagents for the construction of pyridine and pyrimidine derivatives

New 2-aza-1,3-dienes bearing 1 and 3-donor substituents are prepared from N-thioacylacetamidines through deprotonation of N-ylidene acetamidinium iodides. The 2-aza-3-(dimethylamino)-1-(methylthio)-1-phenylbutadiene (3) is trapped in situ by the residual precursor salt acting as a heterodienophile to give the pyrimidine 5. Substituted 2-aza-1-(dimethylamino)-3-(methylthio) analogues react readily with a variety of electron-deficient dienophiles to yield pyridine or pyrimidine derivatives. The stereochemistry of the hetero Diels-Alder reaction in the cases of dimethyl fumarate and acrylonitrile has been assigned by X-ray diffraction analyses of the resulting tetrahydropyridines and corresponds to an exo selectivity. The number and nature of cycloadducts in the cases of dimethyl acetylenedicarboxylate and phenyl isothiocyanate depend on C-4 substitution. The results obtained from the C-4 unsubstituted azabutadiene 8 are explained by an allylic rearrangement involving the 1,3-migration of dimethylamino group in the primary [4+2] adduct.

KOtBu-promoted synthesis of multi-substituted 4-aminopyrimidines from benzonitriles and aliphatic amides

Multi-substituted 4-aminopyrimidines have been prepared from commercially-available benzonitriles and aliphatic amides under transition-metal-free conditions. With KOtBu as the only promoter, the desired pyrimidines were isolated in moderate to excellent yields.

Synthesis of tri-or tetrasubstituted pyrimidine derivatives through the [5+1] annulation of enamidines with either N,N-dimethylformamide dialkyl acetals or orthoesters and their application in a ring transformation of pyrimidines to pyrido[2,3-d]pyrimidin

The [5+1] annulation of enamidines, which were prepared from functionalized silanes, organolithium compounds and two nitriles, with N,N-dimethylformamide dialkyl acetals as the C1 unit is described, leading to the synthesis of tri- and tetrasubstituted py

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.