103607-70-1

Upstream product

• 103607-65-4 1-Phenyl-4-oxo-5-cyano-6-(β-dimethylaminovinyl)-1,4-dihydropyrimidine 
• 91255-14-0 α-Cyano-β-N-phenylaminocrotonamide 
• 68-12-2 N,N-dimethyl-formamide 
• 120650-99-9 (Z)-2-Cyano-3-phenylamino-but-2-enoic acid amide 
• 62-53-3 aniline 
• 62321-92-0 α-cyano-β-dimethylaminocrotonamide 
• 120651-05-0 α-cyano-β-dimethylaminocrotonamide 

Downstream Products

• 103607-75-6 2-chloro-3-cyano-4-anilinopyridine 
• 945017-51-6 3-formyl-2-oxo-4-phenylamino-1,2-dihydropyridine 
• 74990-58-2 1-oxo-1,2-dihydrobenzo[b]-1,6-naphthyridine 
• 74990-54-8 4-anilino-2-oxo-1,2-dihydropyridine 
• 103589-58-8 2-(3-Isopropyl-2-phenyl-oxazolidin-5-ylmethoxy)-4-phenylamino-nicotinonitrile 

Relevant academic research and scientific papers

Study of the reactions of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine with nucleophilic reagents

The reactions of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine (4) with S-, C-, and N-nucleophiles afford stable σ-adducts at position 10. In the base-catalyzed reactions of compound 4 with thiols, the resulting σ-complexes are rearranged into sulfides 14a - c. Sulfides 14b,c undergo the Thorpe - Ziegler cyclization to give 1-aminobenzo[b]thieno[2,3-h][1,6]naphthyridine derivatives 15a,b. The reaction of naphthyridine 4 with aniline affords a mixture of σ-adducts of the C - N and C - C types, while those with aliphatic amines yield 3-amino derivatives 17a - c. In the presence of H2O2, benzonaphthyridine 4 adds peroxycarboxylic acids to give compounds 8a,b. In alkaline medium, adduct 8a is rearranged into 4-aminopyridine-3-carbaldehyde derivative 10.

Synthesis and hydrolytic cleavage of 1-aryl-5-cyano-6-(2- dimethylaminovinyl)-4-oxo(thioxo)-1,4-dihydropyrimidines

1-Aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo-1,4-dihydropyrimidines and their 4-thioxo analogs, which were prepared in three steps from cyanoacetamide and cyanothioacetamide, respectively, were subjected to hydrolysis. In aqueous AcOH, hydrolysis of N-(dimethylaminomethylene)-2-cyano-5-dimethylamino-2,4- pentadieneamide derivatives containing amino groups at position 3 afforded formylpyridones. The reaction of 2-cyano-3-dimethylaminothiocrotonamide with DMF dimethyl acetal gave rise to 3-cyano-4-dimethylamino-2-methylthiopyridine.

Torp-Ziegler cyclization in the synthesis of 3-amino-4-cyanopyrrole derivatives

Polyfunctional derivatives of 3-aminopyrrole have been synthesized from several substituted β-enamino nitriles using Torp-Ziegler cyclization. These compounds are starting materials for further conversions, particularly for the synthesis of pyrrolo[3,2-d]