173316-42-2Relevant academic research and scientific papers
Nanostructured oxytyramine catalyst for the facile one-pot synthesis of cyclohexanecarbonitrile derivatives
Arora, Priya,Rajput, Jaspreet Kaur,Singh, Harminder
, p. 97212 - 97223 (2015/11/28)
The magnetic, recyclable heterogeneous organocatalyst OT@Si@SPIONs has been developed in this report, with the aim of synthesizing cyclohexanecarbonitriles. The prepared nanocatalyst was fully characterized by various techniques and its catalytic activity
Conformational Switching and the Synthesis of Spiro[2H-indol]-3(1H)-ones by Radical Cyclization
Sulsky, Richard,Gougoutas, Jack Z.,DiMarco, John,Biller, Scott A.
, p. 5504 - 5510 (2007/10/03)
Radical cyclization of 1-(2-bromophenylamino)cyclohexanecarbonitriles (3, X = CH) and 4-(2-bromophenylamino)-4-piperidinecarbonitriles (3, X = N) provide spiro[2H-indole-2-cyclohexan]-3(1H)-imines (5, X = CH) and spiro[2H-indole-2,4′-piperidin]-3(1H)-imines (5, X = N), respectively, in 33-57% yields. This contradicts a recent report that 1-(2-bromophenylamino)cyclohexane-carbonitrile (3, X-R2 = CH2), treated under apparently identical conditions, led only to nitrile transfer product 6 (X-R2 = CH2). Acidic hydrolyses of the imines provide the corresponding ketones 2 in quantitative yields. Single-crystal X-ray analyses of ketone 2e and nitrile 3e indicate that the relative configuration of the aromatic nitrogen has been inverted during the cyclization. In addition, NOE NMR analyses of spiroindolepiperidine 2c and its aniline-nitrogen-methylated analogue 10a show that the relative conformation of the piperidine ring has inverted. Thus, methylation of 2c acts as a conformational "switch" for the spiroindolepiperidine ring system.
Synthesis of 2-(alkylamino)benzonitriles from α-(bromoarylamino)nitriles
Cossy,Poitevin,Pardo,Peglion
, p. 1368 - 1370 (2007/10/02)
The treatment of α-(bromoarylamino)nitriles with Bu3SnH/AIBN induced 1,4-cyano group migration which led to 2-(alkylamino)benzonitriles.
