10562-04-6Relevant academic research and scientific papers
Robust Acenaphthoimidazolylidene Palladacycles: Highly Efficient Catalysts for the Amination of N-Heteroaryl Chlorides
Deng, Qinyue,Zhang, Yang,Zhu, Haibo,Tu, Tao
, p. 2364 - 2368 (2017)
A series of robust N-heterocyclic carbene palladacycles have been successfully developed. These showed high catalytic activity and selectivity toward the challenging amination of N-heteroaryl chlorides. Different primary and secondary amines were fully compatible with this catalytic system. Remarkably, no double amination products could be detected when primary amines were utilized in our catalytic transformation. Furthermore, the protocol has been successfully extended to synthesize rosiglitazone, a clinical drug for diabetes mellitus, highlighting its potential pharmaceutical feasibility.
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
, 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.
Heteroatom directed photoannulation: synthesis of indoloquinoline alkaloids: cryptolepine, cryptotackieine, cryptosanguinolentine, and their methyl derivatives
Dhanabal,Sangeetha,Mohan
, p. 6258 - 6263 (2007/10/03)
A three-step synthesis of indoloquinoline alkaloids is described. The reaction of 2,3 and 4-substituted haloquinolines with anilines afforded the respective anilinoquinolines, which upon photocyclization gave the indoloquinolines. By regioselective methylation on quinoline nitrogen, furnished the alkaloids cryptotackieine, cryptosanguinolentine, cryptolepine, and the synthetic isomer isoneocryptolepine. Their methyl derivatives were also synthesized in search of new antiplasmodial drugs and DNA intercalating agents.
Synthesis of dibenzo(b,g)-5-methyl-1,8-naphthyridines
Kidwai,Kohli
, p. 248 - 249 (2007/10/03)
A series of 1,8-naphthyridines have been synthesised. 2-Hydroxy-4-methylquinoline 1 on reaction with PCI5/POCl3 gives 2-chloro-4-methylquinoline 2 which on treatment with substituted anilines yields 2-quinolinamines 3a-e. Cyclisation in situ affords the title compounds 4a-e using phosphorus oxychloride and dimethyl formamide.
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
