38560-27-9Relevant academic research and scientific papers
Peptidomimetics and Methods of Using the Same
-
, (2018/03/25)
Disclosed herein are compounds useful for modulating the mu-opioid receptor (“MOR”) and/or delta-opioid receptor (“DOR”), and methods of using these compounds to treat diseases and conditions, such as pain. In particular, disclosed herein are compounds of
Synthesis of new tricyclic 5,6-dihydro-4H-benzo[b][1,2,4]tri-azolo[1,5-d][1,4]diazepine derivatives by [3+ + 2]-cyclo-addition/rearrangement reactions
Luan, Lin-bo,Song, Zi-jie,Li, Zhi-ming,Wang, Quan-rui
, p. 1826 - 1833 (2018/08/21)
Two new series of tricyclic heterocycles, namely 5,6-dihydro-4H-benzo[b][1,2,4]triazolo[1,5-d][1,4]diazepinium salts 10 and the related neutral, free bases 13 were synthesized from 4-acetoxy-1-acetyl-4-phenylazo-1,2,3,4-tetrahydroquinolines 8 and nitriles 9 in the presence of aluminium chloride by the [3+ + 2]-cycloaddition reaction of the in situ generated azocarbenium intermediates 14 followed by a ring-expansion rearrangement. In the rearrangement reaction, the phenyl substituent in the initially formed spiro-triazolium adducts 16 underwent a [1,2]-migration from C(3) to the electron-deficient N(2). This led to the ring expansion from 6-membered piperidine to 7-membered diazepine furnishing the tricyclic 1,2,4-triazole-fused 1,4-benzodiazepines.
Asymmetric Synthesis of Cyclopentene-Fused Tetrahydroquinolines via N-Heterocyclic Carbene Catalyzed Domino Reactions
Zhao, Long,Li, Sun,Wang, Lei,Yu, Shun,Raabe, Gerhard,Enders, Dieter
, p. 2523 - 2532 (2018/05/28)
A new strategy for the N-heterocyclic carbene catalyzed asymmetric synthesis of cyclopentene-fused tetrahydroquinoline derivatives has been developed. The one-pot organocatalytic domino protocol allows a direct entry to the characteristic cyclopenta[ c ]tetrahydroquinoline core of many alkaloids and some potential drugs employing readily available quinolinone and enal substrates in good domino yields and stereoselectivities.
Asymmetric Synthesis and in Vitro and in Vivo Activity of Tetrahydroquinolines Featuring a Diverse Set of Polar Substitutions at the 6 Position as Mixed-Efficacy μ Opioid Receptor/δ Opioid Receptor Ligands
Bender, Aaron M.,Griggs, Nicholas W.,Anand, Jessica P.,Traynor, John R.,Jutkiewicz, Emily M.,Mosberg, Henry I.
, p. 1428 - 1435 (2015/09/01)
We previously reported a small series of mixed-efficacy μ opioid receptor (MOR) agonist/δ opioid receptor (DOR) antagonist peptidomimetics featuring a tetrahydroquinoline scaffold and showed the promise of this series as effective analgesics after intrape
Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones
Fang, Yuesi,Rogness, Donald C.,Larock, Richard C.,Shi, Feng
, p. 6262 - 6270 (2012/09/22)
N-Unsubstituted β-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.
Synthesis of 2,3-dihydro-4(1H)-quinolones and the corresponding 4(1H)-quinolones via low-temperature fries rearrangement of N-arylazetidin-2- ones
Lange, Jens,Bissember, Alex C.,Banwell, Martin G.,Cade, Ian A.
experimental part, p. 454 - 470 (2011/10/09)
N-Arylazetidin-2-ones of the general form 1, which are readily prepared by GoldbergBuchwald-type copper-catalyzed coupling of N-unsubstituted azetidin-2-ones with the relevant aryl halide or using Mitsunobu cyclization processes, undergo smooth Fries-rearrangement in triflic acid at 018°C to give the isomeric 2,3-dihydro-4(1H)-quinolones (2). Dehydrogenation of the latter compounds using 10% Pd on C in 1.0M aqueous sodium hydroxide/propan-2-ol mixtures at ca. 82°C provides the corresponding 4(1H)-quinolones (3).
