Expanding the tetrahydroquinoline pharmacophore

Palladium‐ and Ruthenium‐Catalyzed Intramolecular Carbene CAr−H Functionalization of γ‐Amino‐α‐diazoesters for the Synthesis of Tetrahydroquinolines

“…The examples in Ta bles1and 2, below,c onfirm the generality and functional group tolerance of these reactions. As observed in Ta ble 1, no competition from sp 3 -CÀHi nsertion was observed upon startingf rom para-a nd meta-substituted N-isopropylanilines ( meta-Substituted anilines 1e-i also underwent chemoselective sp 2 -C Ar ÀHf unctionalization to give the corresponding tetrahydroquinolines with either the Pd 0 or Ru-1 catalysts;t he latter once again afforded the highest reaction yields ( Table 1, entries [15][16][17][18][19][20][21][22][23][24][25]. With these substrates, the regioselectivity of insertion( 5-X/7-X ratio) seems to be controlled by ac ombination of steric and electronic effects.…”

“…The extensive bioactivity of tetrahydroquinolines, including antitumor, antiviral, antibacterial,a ntimalarial, and antifungal activity,i sw ell documented, and the development of efficient procedures for their preparation is therefore of considerable interest. [22,23] The aim of the current work wast oi nvestigate the feasibility of using both palladium(0) andG rubbs catalysts to promote intramolecular carbene sp 2 -C Ar ÀHf unctionalization and to identifyd ifferences in the reactivities and selectivities between the two TMs. Thus,herein, we report af ullaccount of our experimental and computational studies on TM-catalyzed sp 2 -C Ar ÀHf unctionalization in the search for as uitablem ethodology for the synthesis of tetrahydroquinolines.…”

Synthesis of Novel Spiro-Tetrahydroquinoline Derivatives and Evaluation of Their Pharmacological Effects on Wound Healing

“…Delightfully, the substrate having aldehyde (R 1 = H) group reacted well with 2a to afford the corresponding product 3i in 95% yield within 3 h (Table 1, entry 11). As similar as R 2 , substrates bearing electron-withdrawing R 1 groups (1c and 1d) more efficiently furnished the desired products 3j and 3k compared to the electron-donating group such as 1e (Table 1, entries [12][13][14]. When substrate with ester group 1f was employed as the reactant, the corresponding product could not be found in the reaction (Table 1, entry 15).…”

“…Some quinoline derivatives were found to have wound healing activity [10][11][12][13]. Tetrahydroquinoline derivatives, which are the reduced form of quinolines, were used as antibacterials, antitumor and anti-HIV agents [14]. However, there are very few reports about tetrahydroquinoline on wound healing even though their structures are so similar to each other [15].…”

A thiadiazolopyridine-functionalized Zr(iv)-based metal–organic framework for enhanced photocatalytic synthesis of tetrahydroquinolines under visible light

“…[6][7][8][9] The tetrahydroquinoline (THQ) motif is an important structural scaffold of many natural products and medicinal agents that have demonstrated a variety of biological activities. 10,11 Due to their widespread existence in natural products and pharmaceutical agents, a number of methods have been developed for the construction of THQ skeleton. [12][13][14] Among them, the photochemical approach mediated by visible light offered a more sustainable methodology in this process.…”