80334-76-5Relevant academic research and scientific papers
Highly efficient Rh-catalyzed asymmetric hydrogenation of α,β-unsaturated nitriles
Yan, Qiaozhi,Kong, Duanyang,Li, Meina,Hou, Guohua,Zi, Guofu
supporting information, p. 10177 - 10181 (2015/09/01)
A highly efficient enantioselective hydrogenation of α,β-unsaturated nitriles catalyzed by Rh-(R,R)-f-spiroPhos complex has been developed. With Rh-(R,R)-f-spiroPhos catalyst and under mild conditions, a wide range of α,β-unsaturated nitriles including the (E)- and (Z)-isomers of 3-alkyl-3-aryl, 3,3-diaryl, and 3,3-dialkyl α,β-unsaturated nitriles were hydrogenated to the corresponding chiral nitriles with excellent enantioselectivities (up to 99.9% ee) and high turnover numbers (TON up to 10,000).
PREPARATION OF CINNOLINE-3,4-DICARBONITRILE AND -DICARBOXYLIC ACID
Ames, D. E.,Bull, D.
, p. 2489 - 2492 (2007/10/02)
Attempts to prepare cinnoline-3,4-dicarboxylic acid from 3,4-dimethylcinnoline failed owing to the unreactivity of the 3-Me group.Successive treatment of 3-bromo-4-chlorocinnoline with sodium toluene-p-sulphinate and potassium cyanide in dimethylformamide (DMF) gave 4-toluene-p-sulphonylcinnoline-3-carbonitrile and then cinnoline-3,4-dicarbonitrile (82percent).Hydrolysis yielded cinnoline-3,4-dicarboxylic acid (53percent).Cinnoline-3,4-dicarbonitrile undergoes nucleophylic displacement of either the 4- or the 3-cyano group by ammonia or amine to give 4-amino- and 4-benzylaminocinnoline-3-carbonitrile but 3-dimethylamino-cinnoline-4-carbonitrile.
