38253-19-9Relevant academic research and scientific papers
Metal and Oxidant Free Construction of Substituted- and/or Polycyclic Indoles: A Useful Alternative to Bischler and Related Syntheses
De Crescentini, Lucia,Favi, Gianfranco,Mantellini, Fabio,Mari, Giacomo,Santeusanio, Stefania
supporting information, (2020/08/27)
A wide range of substituted indoles or polycyclic derivatives containing the indole core are easily accessible by acidic treatment of aromatic amines and 1,2-diaza-1,3-dienes. Unlike the related indole-Bischler synthesis, the regioselectivity of the method here reported is unique and predictable, the yields are generally good and also electron withdrawing substituted indoles are smoothly recovered.
Dynamic kinetic resolution allows a highly enantioselective synthesis of cis-α-aminocycloalkanols by ruthenium-catalyzed asymmetric hydrogenation
Liu, Sheng,Xie, Jian-Hua,Wang, Li-Xin,Zhou, Qi-Lin
, p. 7506 - 7508 (2008/09/17)
(Chemical Equation Presented) Resolutely dynamic hydrogenation: A highly efficient asymmetric hydrogenation of racemic N,N-disubstituted α-aminocycloalkanones involving dynamic kinetic resolution in the presence of a ruthenium catalyst gives chiral α-aminocycloalkanols with excellent enantioselectivities and cis diastereoselectivities (see scheme). A synthesis of optically pure U-(-)-50488 based on this reaction is reported.
Light-induced Reactions of 2-(N-Alkyl-N-arylamino)cyclohexanones and Related Amino-cycloalkanones: Formation of 7-Azabicyclooctan-1-ols
El-Hamamy, Ahmad A.,Hill, John,Townend, John
, p. 573 - 580 (2007/10/02)
On irradiation, 2-(N-alkyl-N-arylamino)cyclohexanones (aryl = Ph; alkyl = Me, benzyl, allyl, Et, CH2CH2Ph, or CH2CF3; or aryl = p-tolyl; alkyl = Me) (10) or (20), 4,4-dimethyl-2-(N-methylanilino)-cyclohexanone (24), and 2-(N-methylanilino)-5α-cholestan-3-one (26) underwent type-II cyclisation to afford azetidinol (7-azabicyclooctan-1-ol) derivatives.In general, fission to give the corresponding N-alkyl-N-arylamine and ketone was a minor photoreaction.When the alkyl group of the 2-(N-alkylanilino)cyclohexanone had the structure -CH(R)CH2R', a double 1,5-hydrogen transfer occurred leading to a low yield of a 2-anilinocyclohexanol (31a).Photolysis of 2-anilinocyclohexanone (32a) gave a little of the direct-fission product aniline (17a), and the alkylamino-ketones 2-(NN-diethylamino)- (32b) and 2-(N-pyrrolidino)-cyclohexanone (32c) underwent no significant photoreaction in methanol.The isolation of indan-1-one and N-trideuteriomethylaniline on irradiation of 2-(N-trideuteriomethylanilino)-indan-1-one (33b) in diethyl ether indicated that the photoreaction was a direct Cα-N bond fission and not a type-II fission.
