92210-62-3Relevant articles and documents
1,4-addition of TMSCCl3 to nitroalkenes: Efficient reaction conditions and mechanistic understanding
Wu, Na,Wahl, Benoit,Woodward, Simon,Lewis, William
supporting information, p. 7718 - 7724 (2014/07/07)
Improved synthetic conditions allow preparation of TMSCCl3 in good yield (70 %) and excellent purity. Compounds of the type NBu4X [X=Ph3SiF2 (TBAT), F (tetrabutylammonium fluoride, TBAF), OAc, Cl and Br] act as catalytic promoters for 1,4-additions to a range of cyclic and acyclic nitroalkenes, in THF at 0-25 °C, typically in moderate to excellent yields (37-95 %). TBAT is the most effective promoter and bromide the least effective. Multinuclear NMR studies (1H, 19F, 13C and 29Si) under anaerobic conditions indicate that addition of TMSCCl3 to TBAT (both 0.13 M) at -20 °C, in the absence of nitroalkene, leads immediately to mixtures of Me3SiF, Ph3SiF and NBu4CCl3. The latter is stable to at least 0 °C and does not add nitroalkene from -20 to 0 °C, even after extended periods. Nitroalkene, in the presence of TMSCCl3 (both 0.13 M at -20 °C), when treated with TBAT, leads to immediate formation of the 1,4-addition product, suggesting the reaction proceeds via a transient [Me 3Si(alkene)CCl3] species, in which (alkene) indicates an Si O coordinated nitroalkene. The anaerobic catalytic chain is propagated through the kinetic nitronate anion resulting from 1,4 CCl3 - addition to the nitroalkene. This is demonstrated by the fact that isolated NBu4[CH2=NO2] is an efficient promoter. Use of H2C=CH(CH2)2CH=CHNO 2 in air affords radical-derived bicyclic products arising from aerobic oxidation. Understanding TMSCCl3: The synthesis and reactivity of TMSCCl3 has been investigated. The mechanism of 1,4-CCl3 addition to nitroalkenes begins with nitroalkene coordination, followed by the attack of an external fluoride ion, and does not involve the formation of NBu4[Me3SiFCCl3] (see figure).
Advances toward new antidepressants with dual serotonin transporter and 5-HT1A receptor affinity within a class of 3-aminochroman derivatives. Part 2
Hatzenbuhler, Nicole T.,Baudy, Reinhardt,Evrard, Deborah A.,Failli, Amedeo,Harrison, Boyd L.,Lenicek, Steven,Mewshaw, Richard E.,Saab, Annmarie,Shah, Uresh,Sze, Jean,Zhang, Minsheng,Zhou, Dahui,Chlenov, Michael,Kagan, Michael,Golembieski, Jeannette,Hornby, Geoffrey,Lai, Margaret,Smith, Deborah L.,Sullivan, Kelly M.,Schechter, Lee E.,Andree, Terrance H.
scheme or table, p. 6980 - 7004 (2009/11/30)
Novel compounds combining a 5-HT1A moiety (3-aminochroman scaffold) and a 5-HT transporter (indole analogues) linked through a common basic nitrogen via an alkyl chain attached at the 1- or 3-position of the indole were evaluated for dual affin
Synthesis and biological evaluation of novel compounds within a class of 3-aminochroman derivatives with dual 5-HT1A receptor and serotonin transporter affinity
Hatzenbuhler, Nicole T.,Evrard, Deborah A.,Harrison, Boyd L.,Huryn, Donna,Inghrim, Jennifer,Kraml, Christina,Mattes, James F.,Mewshaw, Richard E.,Zhou, Dahui,Hornby, Geoffrey,Lin, Qian,Smith, Deborah L.,Sullivan, Kelly M.,Schlechter, Lee E.,Beyer, Chad E.,Andree, Terrance H.
, p. 4785 - 4789 (2007/10/03)
Compounds containing a 5-carbamoyl-8-fluoro-3-amino-3,4-dihydro-2H-1- benzopyran and a 3-alkylindole moiety linked through a common basic nitrogen were prepared and evaluated for 5-HT1A affinity, serotonin rat transporter affinity, and functional antagonist activity in vitro. 26a was found to be the most potent and selective compound in this series and was shown to possess neurochemical activity in vivo by producing acute and rapid increases in 5-HT in the rat frontal cortex.
New Direct Synthesis of 3-Nitro-2H-chromenes Using Nitroethylene
Neirabeyeh, Mamdouh Al,Koussini, Rafik
, p. 783 - 788 (2007/10/02)
The treatment of substituted 2-hydroxybenzaldehydes by nitroethylene, prealably prepared or generated in situ within the reaction, in the presence of di-n-butylamine gave 3-nitro-2H-chromenes in fair to excellent yields.
