42836-16-8Relevant academic research and scientific papers
Synthesis of Tetrahydroquinolines via Borrowing Hydrogen Methodology Using a Manganese PN3Pincer Catalyst
Hofmann, Natalie,Homberg, Leonard,Hultzsch, Kai C.
supporting information, p. 7964 - 7970 (2020/11/02)
A straightforward and selective synthesis of 1,2,3,4-tetrahydroquinolines starting from 2-aminobenzyl alcohols and simple secondary alcohols is reported. This one-pot cascade reaction is based on the borrowing hydrogen methodology promoted by a manganese(I) PN3 pincer complex. The reaction selectively leads to 1,2,3,4-tetrahydroquinolines thanks to a targeted choice of base. This strategy provides an atom-efficient pathway with water as the only byproduct. In addition, no further reducing agents are required.
Mechanistic studies of intramolecular CH insertion reaction of arylnitrenes: Isotope effect, configurational purity and radical clock studies
Murata, Shigeru,Tsubone, Yasuhiro,Kawai, Reina,Eguchi, Daisuke,Tomioka, Hideo
, p. 9 - 20 (2007/10/03)
In order to reveal the mechanism of the intramolecular CH insertion of arylnitrenes, three experiments were carried out: measurement of isotope effects, determination of the extent of configurational retention and radical clock studies. Irradiation of the deuterium-substituted azide 4-d in an inert solvent exclusively afforded the indolines 5-h and 5-d, in which the kinetic isotope effect kH/kD on the intramolecular CH insertion of the nitrene was evaluated as 12.6-14.7 at room temperature. A chiral Chromatographic analysis of the indoline 11 obtained from the optically active azide (S)-6 revealed that the enantiomeric purity of the starting azide was almost completely lost during the intramolecular CH insertion of the photolytically generated nitrene (enantiomeric excess 10%). The thermolysis of the azide 7 at 180°C mainly gave a mixture of the cyclopropyl ring-opened products 20-22, together with the intramolecular CH insertion product with an intact cyclopropyl ring 19. On the basis of these observations, we concluded that the intramolecular CH insertion of the nitrene proceeds primarily by the hydrogen abstraction-recombination mechanism. We propose, however, a small contribution of the concerted mechanism to the intramolecular CH insertion, based on the solvent dependence of the isotope effect and the extent of the configurational retention. Copyright
Switching Androgen Receptor Antagonists to Agonists by Modifying C-Ring Substituents on Piperidinoquinolinone
Zhi, Lin,Tegley, Christopher M.,Marschke, Keith B.,Jones, Todd K.
, p. 1008 - 1012 (2007/10/03)
New nonsteroidal human androgen receptor (hAR) agonists were developed from an hAR antagonist pharmacophore, 2(1H-piperidinoquinolinone. (+/-)-trans-7,8-diethyl-4-trifluoromethyl-2(1H)-piperidinoquinolinone was synthesized and demonstrated p
