81102-84-3Relevant academic research and scientific papers
Base-controlled chemoselectivity reaction of vinylanilines with isothiocyanates for synthesis of quinolino-2-thione and 2-aminoquinoline derivatives
Zhang, Xi,Wang, Tong-Lin,Huo, Cong-De,Wang, Xi-Cun,Quan, Zheng-Jun
, p. 3114 - 3117 (2018/03/28)
Here, we report a base-controlled chemo-selective reaction of vinylanilines with alkyl/aryl isothiocyanates to afford quinolino-2-thione and 2-aminoquinoline derivatives. The quinolino-2-thiones could be obtained in high yields in the presence of Et3N. Particularly interesting is that the reaction could produce the 2-aminoquinolines in the presence of K3PO4 with high selectivity.
Cu-catalyzed aerobic oxidative cyclizations of 3-N-hydroxyamino-1,2-propadienes with alcohols, thiols, and amines to form α-O-, S-, and N-substituted 4-methylquinoline derivatives
Sharma, Pankaj,Liu, Rai-Shung
supporting information, p. 4590 - 4594 (2015/03/18)
A one-pot, two-step synthesis of α-O-, S-, and Nsubstituted 4-methylquinoline derivatives through Cu-catalyzed aerobic oxidations of N-hydroxyaminoallenes with alcohols, thiols, and amines is described. This reaction sequence involves an initial oxidation of N-hydroxyaminoallenes with NuH (Nu = OH, OR, NHR, and SR) to form 3-substituted 2-en-1-ones, followed by Bronsted acid catalyzed intramolecular cyclizations of the resulting products. Our mechanistic analysis suggests that the reactions proceed through a radical-type mechanism rather than a typical ni-trone-intermediate route. The utility of this new Cu-catalyzed reaction is shown by its applicability to the synthesis of several 2-amino-4-methylquinoline derivatives, which are known to be key precursors to several bioactive molecules.
A Versatile Synthesis of Functionalised 2-Aminoquinolines by Mercury Controlled Cyclisation of 2-Vinylphenylthioureas
Wiggall, Kenneth J.,Richardson, Stewart K.
, p. 867 - 870 (2007/10/02)
4-(4-Hydroxyphenyl)-2-phenylamino-1,8-naphthyridine was prepared via cyclization of N-phenyl-N'-3-(4-hydroxyphenethen-1-yl)pyridin-2-ylthiourea in the presence of mercuric oxide.Derivatives of 4-methyl-2-aminoquinolines were prepared in a similar manner f
