89990-51-2Relevant articles and documents
Reagent-switch controlled metal-free intermolecular geminal diamination and aminooxygenation of vinylarenes
Venkatesan Balaji, Pandur,Chandrasekaran, Srinivasan
, p. 1095 - 1104 (2016)
We report here the first general method for the geminal diamination and an intermolecular metal-free, geminal aminooxygenation of vinylarenes using hypervalent iodine reagent. A new m-CPBA mediated geminal aminooxygenation is also reported. A novel reagent-switch for the control of migrating group by controlling the two independent geminal addition paths is developed. Deuterium labelling studies and the control studies have provided unambiguous evidences for the phenyl migration and hydride migration in the oxidative geminal difunctionalization process mediated by PhI(OCOCF3)2and m-CPBA, respectively through a semi-pinacol rearrangement.
Investigation of macrocyclisation routes to 1,4,7-triazacyclononanes: Efficient syntheses from 1,2-ditosylamides
Stones, Graham,Tripoli, Regis,McDavid, Colin L.,Roux-Duplgtre, Kewin,Kennedy, Alan R.,Sherrington, David C.,Gibson, Colin L.
, p. 374 - 384 (2008/10/09)
Two routes to the synthesis of a cyclohexyl-fused 1,4,7-triazacyclononane involving macrocyclisations of tosamides have been investigated. In the first approach, using a classic Richman-Atkins-type cyclisation of a cyclohexyl-substituted 1,4,7-tritosamide
Copper-catalyzed 1,2-double amination of 1-halo-1-alkynes. Concise synthesis of protected tetrahydropyrazines and related heterocyclic compounds
Fukudome, Yasuhiro,Naito, Hiroyuki,Hata, Takeshi,Urabe, Hirokazu
, p. 1820 - 1821 (2008/09/18)
Reaction of N,N′-di(p-toluenesulfonyl)-1,2-diamine, 1-bromo-1-alkyne, K3PO4, and a catalytic amount of CuI in hot DMF afforded N,N′-di(p-toluenesulfonyl)-1,2,3,4-tetrahydropyrazines in good yields. The reaction most likely involves (i) monoalkynylation of the diamine derivative with 1-bromo-1-alkyne, and (ii) 6-endo-dig ring closure between the acetylenic bond and another sulfonylamine moiety of the diamine. When the starting 1,2-diamine derivative was replaced with N,N′-di(p-toluenesulfonyl)-1,3-diamine or N-(p-toluenesulfonyl)-2-amino-1-ethanol, the corresponding seven-membered diazacycle or six-membered N,O-heterocycle was produced. In addition, 1,1-dibromo-1-alkene could be used in place of 1-bromo-1-alkyne. Copyright