3835-21-0Relevant academic research and scientific papers
The first intermolecular Friedel-Crafts acylation with β-lactams
Anderson, Kevin W.,Tepe, Jetze J.
, p. 459 - 461 (2002)
(Equation Presented) The first intermolecular Friedel-Crafts acylation of a variety of aromatic substrates with azetidinones is described. The Friedel-Crafts acylations are performed under very mild conditions, using trifluoromethanesulfonic acid to produce β-amino aromatic ketones in excellent yields.
2,3-dihydro-1H-quinoline-4-ketone thiosemicarbazone derivatives as well as preparation method and application thereof
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Paragraph 0076; 0080-0082; 0198; 0202-0204, (2019/04/04)
The invention discloses 2,3-dihydro-1H-quinoline-4-ketone thiosemicarbazone derivatives as well as a preparation method and application thereof. The structural formula of the derivatives is as shown in a formula (I): (the formula is as shown in the description), wherein R1 is halogen, alkyl or alkoxy; R2 is hydrogen, halogen or alkoxy; R3 is hydrogen or halogen; R4 is hydrogen or halogen; X is hydrogen, acetyl or nitryl; and Y is hydrogen or phenyl. The derivatives can obviously inhibit proliferation of tumor cells, and has significant inhibition effect on multiple cancer cell strains such asbreast cancer cells, melanoma cells and prostatic cancer cells; and the anti-tumor activity is obviously better than that of a broad-spectrum anti-cancer medicine cis-platinum. In addition, the preparation process of the derivatives is simple, the conditions are mild, the sources of the raw materials are rich, the production cost is low, and potential medicinal value and good application prospectin the aspect of preparing a novel anti-tumor medicine are achieved.
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
supporting information, 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.
2 - [6-methoxy-3 - (2,3-dichlorophenyl) methyl-4-oxo -1,4-dihydro -1 (4H)-quinolyl] method for the preparation of acetic acid
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, (2016/10/08)
The invention provides a preparation method of 2-(6-methoxy-3-(2, 3-dichlorophenyl) methyl-4-oxo-1, 4-dihydro-1(4H)-quinolyl) acetic acid. The preparation method comprises the following steps: by taking 3-(4-methoxyanilino) sodium propionate as a raw material, performing amino protection treatment to prepare 3-(N-protecting group-4-methoxyanilino) propionic acid, performing Friedel-Crafts acylation reaction to prepare N-protecting group-6-methoxy-2, 3-dihydroquinolinone, and further performing deprotection treatment to prepare an intermediate, namely 6-methoxy-2, 3-dihydro-4 (1H)-quinolinone; by taking the intermediate, namely 6-methoxy-2, 3-dihydro-4 (1H)-quinolinone as a raw material, performing N-alkylation, hydrolysis and condensation reaction to prepare a target product. By adopting the preparation method, the use of a large amount of polyphosphoric acid (PPA) can be avoided, the process is environment-friendly, and the preparation method is more conductive to industrial production.
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
experimental part, 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.
, 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).
Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists
Schmidt, Robert G.,Bayburt, Erol K.,Latshaw, Steven P.,Koenig, John R.,Daanen, Jerome F.,McDonald, Heath A.,Bianchi, Bruce R.,Zhong, Chengmin,Joshi, Shailen,Honore, Prisca,Marsh, Kennan C.,Lee, Chih-Hung,Faltynek, Connie R.,Gomtsyan, Arthur
scheme or table, p. 1338 - 1341 (2011/04/23)
Novel chroman and tetrahydroquinoline ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that aryl substituents on the 7- or 8-position of both bicyclic scaffolds imparted the best in vitro potency at TRPV1. The most potent chroman ureas were assessed in chronic and acute pain models, and compounds with the ability to cross the blood-brain barrier were shown to be highly efficacious. The tetrahydroquinoline ureas were found to be potent CYP3A4 inhibitors, but replacement of bulky substituents at the nitrogen atom of the tetrahydroisoquinoline moiety with small groups such as methyl can minimize the inhibition.
Chromanylurea compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor and uses thereof
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Page/Page column 51, (2008/06/13)
Compounds that are antagonists of the VR1 receptor, having formula (I) [image] or a pharmaceutically acceptable salt, prodrug, or salt of a prodrug thereof, wherein A1, A2, A3, A4, R7, R8, R9, X, Y, Z, L, n, and m, are as defined herein, and are useful in disorders prevented or ameliorated by inhibiting the VR1 receptor.
Trifluoromethanesulfonic acid catalyzed Friedel-Crafts acylation of aromatics with β-lactams
Anderson, Kevin W.,Tepe, Jetze J.
, p. 8475 - 8481 (2007/10/03)
N-Protected and unprotected 2-azetidinones, protolytically activated by superacidic trifluoromethanesulfonic acid, react with aromatic compounds to give β-amino aromatic ketones in good to excellent yields (65-98%). Non-benzenoid aromatics (pyrrole and ferrocene) produced good yield (64-89%) of the corresponding ketones.
Structure-activity relationships of antimalarial indoloquinolines
Werbel, L. M.,Kesten, S. J.,Turner, W. R.
, p. 837 - 852 (2007/10/02)
Structure-activity relationships have been ascertained and chemical metodology developed for a series of antimalarial 3-chloroindoloquinoline-5-oxides.The basic side chain as well as the ring N-oxide are critical for antimalarial activity as is a bromine or chlorine in position 3.Substitution at positions 7,8,9,10 in not essential, although the most potent analog in our studies was the 8-nitro compound 4vv. indoloquinolines / antimalarial agents
