69689-99-2

Upstream product

• 935-02-4 3-Phenyl-2-propynonitrile 
• 104-94-9 4-methoxy-aniline 
• 614-16-4 Benzoylacetonitrile 

Downstream Products

• 1088711-61-8 (S)-3-((4-methoxyphenyl)amino)-3-phenylpropanenitrile 
• 101290-91-9 5-methoxy-2-phenyl-1H-indole-3-carbonitrile 
• 72694-06-5 (Z)-2-Cyano-3-(4-methoxy-phenylamino)-3-phenyl-dithioacrylic acid ethyl ester 

Relevant academic research and scientific papers

PIDA-mediated oxidative C-C bond formation: Novel synthesis of indoles from n-aryl enamines

A variety of functionalized indoles were synthesized from N-aryl enamines via PIDA-mediated oxidative carbon-carbon bond formation. The features of the present reaction include facilitative preparation of substrates 2, good functional group tolerance, and mild reaction conditions without transition metals.

Dynamic kinetic resolution in the asymmetrie synthesis of β-amino acids by organocatalytic reduction of enamines with trichlorosilane

A new methodology based on the organocatalytic asymmetric hydrosilylation of enamines that allows a direct access to a range of β3 and β2.3-amino acid derivatives was presented. The results show a successful reduction of aromatic substrates, a sterically more hindered ortho-substituted derivatives, and the thiophenyl analogue exhibiting lower reactivity. Fast enamine-imine equilibration is crucial as imines are chiral but racemic, while α-alkyl β-amino acids can be accessed by the symmetrical Mannich reaction. The α-alkyl derivatives have relative and absolute configuration due to their reduction with LiAlH4 into a known amino alcohols. Predominant formation of the anti isomer in 3o is consistent with conformation of the imine intermediate in the catalytic reduction.

Addition of diazoacetonitrile to N-benzylidene-anilines. Synthesis and decomposition of 4-cyano-1,5-diaryl,Δ2-1,2,3-triazolines

Addition of diazoacetonitrile to para-substituted N-benzilidene-anilines has been studied. The addition is easier if the substituent is an electrodonating group. Products obtained are Δ2-1,2,3-triazolines or aziridnes, and enamines resulting from the decomposition of the triazolines with migration of the 5-aryl substituent. Decomposition of the triazolines under various conditions has also been studied.