33350-26-4Relevant articles and documents
4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors
Pechulis, Anthony D.,Beck, James P.,Curry, Matt A.,Wolf, Mark A.,Harms, Arthur E.,Xi, Ning,Opalka, Chet,Sweet, Mark P.,Yang, Zhicai,Vellekoop, A. Samuel,Klos, Andrew M.,Crocker, Peter J.,Hassler, Carla,Laws, Mia,Kitchen, Douglas B.,Smith, Mark A.,Olson, Richard E.,Liu, Shuang,Molino, Bruce F.
, p. 7219 - 7222 (2013/01/15)
Novel 4-phenyl tetrahydroisoquinolines that inhibit both dopamine and norepinephrine transporters were designed and prepared. In this Letter, we describe the synthesis, in vitro activity and associated structure-activity relationships of this series. We also report the ex vivo NET occupancy of a representative compound, 41.
Enantioselective reduction of α-substituted ketones mediated by the boronate ester TarB-NO2
Eagon, Scott,Ball-Jones, Nicholas,Haddenham, Dustin,Saavedra, Jaime,Delieto, Cassandra,Buckman, Matthew,Singaram, Bakthan
supporting information; experimental part, p. 6418 - 6421 (2010/12/30)
A facile and mild reduction procedure is reported for the preparation of chiral secondary alcohols prepared from α-substituted ketones using sodium borohydride and the chiral boronate ester (l)-TarB-NO2. Direct reduction of substituted ketones bearing Lewis basic heteroatoms generally provided secondary alcohols of only modest enantiomeric excess likely due to either competition between the target carbonyl and the functionalized sidechains at the Lewis acidic boron atom in TarB-NO2 or the added steric bulk of the α-sidechain. As an alternative method, these substrates were synthesized using TarB-NO2 via a two-step procedure involving the reduction of an α-halo ketone to a chiral terminal epoxide, followed by regioselective/regiospecific epoxide opening by various nucleophiles. This procedure provides access to a variety of functionalized secondary alcohols including β-hydroxy ethers, thioethers, nitriles, and amines with enantiomeric excesses of 94% and yields up to 98%.
Synthesis of 4-substituted- and 1,4-disubstituted-4-hydroxypyrrolidin-2- ones
Kinsinger, Christopher R.,Tatko, Chad D.,Whelan, Christopher M.,Wilkinson, Timothy J.
, p. 1845 - 1852 (2008/02/02)
This report describes the synthesis of 4-substituted- and 1,4-disubstituted-4-hydroxypyrrolidin-2-ones by cyclization of intermediate γ-aminoesters prepared from alkylbenzylamines, α-bromoketones, and lithio ethyl acetate. Copyright Taylor & Francis Group, LLC.
Heteroatom-guided torquoselective olefination of α-oxy and α-amino ketones via ynolates
Shindo, Mitsuru,Yoshikawa, Takashi,Itou, Yasuaki,Mori, Seiji,Nishii, Takeshi,Shishido, Kozo
, p. 524 - 536 (2008/09/20)
Ynolates were found to react with α-alkoxy-, α-siloxy-, and α -aryloxyketones at room temperature to afford tetrasubstituted olefins with high Z selectivity. Since the geometrical selectivity was determined in the ring opening of the β-lactone enolate intermediates, the torquoselectivity was controlled by the ethereal oxygen atoms. From experimental and theoretical studies, the high Z selectivity is in duced by orbital and steric interactions rather than by chelation. In a similar manner, α-dialkylamino ketones provided olefins with excellent Z selectivity. These products can be easily converted into multisubstituted butenolides and γ-butyrolactams in good yield.
New entry of coupling reaction of phenacylamine derivatives with silylstannane.
Iwai, Yasumasa,Kita, Kumiko,Matsushita, Yoko,Yamauchi, Aiko,Kihara, Masaru
, p. 441 - 443 (2007/10/03)
The new coupling reaction of phenacylamines with silylstannane and lithium diisopropylamide (LDA) is reported. The treatment of a phenacylamine iodide 1 with (trimethylsilyl)tributylstannane (Me3SiSnBu3) and cesium fluoride (CsF) gave a dimerization product 2 having no iodine atom. Reaction of 1 with LDA afforded a dimerization product 3 with an iodine atom. The products 2 and 3 were separated to the meso and racemic isomers, respectively.
The effect of different amine bases in the Swern oxidation of β-amino alcohols
Chrisman, William,Singaram, Bakthan
, p. 2053 - 2056 (2007/10/03)
Swern oxidation of β-amino alcohols containing tertiary amino groups afforded the corresponding α-amino carbonyl compounds in fair to excellent yield. Yields were dependent on the steric requirement of the amine base used for the reaction and were optimiz
A convenient synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolin-4-ols by a novel intramolecular Barbier reaction and by an insertion reaction: Reaction scope and limitations
Kihara, Masaru,Kashimoto, Minoru,Kobayashi, Yoshimaro
, p. 67 - 78 (2007/10/02)
4-Substituted 1,2,3,4-tetrahydroisoquinolin-4-ols were prepared from N-(2-iodobenzyl)phenacylamines by an intramolecular Barbier reaction with butyllithium and by an insertion reaction with zerovalent nickel. The scope and limitations of these reactions were discussed.
A New Synthesis of 1,2,3,4-Tetrahydro-2-methyl-4-phenylisoquinolines
Venkov, Atanas P.,Vodenicharov, Daniel M.
, p. 253 - 255 (2007/10/02)
1,2,3,4-Tetrahydro-2-methyl-4-phenylisoquinolines 6 are obtained from aromatic aldehydes 1, methyl amine and α-haloacetophenones 2 in the presence of sodium borohydride followed by cyclization with sulfuric acid and zinc in methanol.
A NEW INTRAMOLECULAR BARBIER REACTION OF N-(2-IODOBENZYL)PHENACYLAMINES: A CONVENIENT SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLIN-4-OLS
Kihara, Masaru,Kashimoto, Minoru,Kobayashi, Yoshimaro,Kobayashi, Shigeru
, p. 5347 - 5348 (2007/10/02)
4-Phenyl-1,2,3,4-tetrahydroisoquinolin-4-ols were prepared by an intramolecular Barbier reaction of N-(2-iodobenzyl)phenacylamines with butyllithium in good yields.
N,N-DIALKYLAMINOMETHYLTRIBUTYLTINS AS PRECURSORS OF (N,N-DIALKYLAMINOMETHYL) KETONES
Verlhac, Jean-Baptiste,Quintard, Jean-Paul
, p. 2361 - 2364 (2007/10/02)
(N,N-Dialkylaminomethyl) ketones have been obtained in good yields (64-87percent) by reacting (N,N-dialkylaminomethyl) tributyltins with acyl chlorides.The mildness of the experimental conditions is compatible with the presence of functional groups like a
