71493-74-8Relevant academic research and scientific papers
Propargylamine-selective dual fluorescence turn-on method for post-synthetic labeling of DNA
Nguyen, Van Thang,Pandith, Anup,Seo, Young Jun
, p. 3199 - 3202 (2020/03/23)
We have developed a propargylamine-selective dual fluorescence turn-on system, using ylidenemalononitrile enamines, for post-synthetic DNA labeling, allowing the direct monitoring of DNA using dual emission in living cells.
Ylidenemalononitrile enamines as fluorescent "turn-on" indicators for primary amines
Longstreet, Ashley R.,Jo, Minyoung,Chandler, Rebecca R.,Hanson, Kenneth,Zhan, Naiqian,Hrudka, Jeremy J.,Mattoussi, Hedi,Shatruk, Michael,McQuade, D. Tyler
, p. 15493 - 15496 (2015/01/08)
Ylidenemalononitrile enamines undergo rapid amine exchange followed by a cyclization with primary amines to yield fluorescent products with emission intensities as high as 900 times greater than the starting materials. After identifying the fluorescent species by X-ray crystallography, we demonstrate that the rate of amine exchange is substrate dependent and that by simple structural variation the fluorescence can be tuned over the entire visible spectrum. We further demonstrate their potential application in biomolecule labeling.
Improved synthesis of mono- and disubstituted 2-halonicotinonitriles from alkylidene malononitriles
Longstreet, Ashley R.,Campbell, Brian S.,Gupton, B. Frank,McQuade, D. Tyler
, p. 5298 - 5301 (2013/11/06)
Pyridines with 2,3,4 and/or 5 substitution remain challenging to prepare. Existing strategies to form multisubstituted 2-halonicotinonitriles via enamines suffer from dimerization of the starting alkylidene malononitriles resulting in low yields. Through alteration of reaction conditions, a new high yielding method into enamines was realized by condensing DMF-DMA and alkylidene malononitriles in the presence of substoichiometric acetic anhydride. Cyclization of the resulting enamines under Pinner conditions provided 2-halonicotinonitriles in high overall yields.
