5099-95-6Relevant academic research and scientific papers
Enantioselective Synthesis of Cyclopropanone Equivalents and Application to the Formation of Chiral β-Lactams
Jang, Yujin,Johnson, J. Drake,Jung, Myunggi,Lindsay, Vincent N. G.,Poteat, Christopher M.,Williams, Rachel G.
supporting information, p. 18655 - 18661 (2020/08/21)
Cyclopropanone derivatives have long been considered unsustainable synthetic intermediates because of their extreme strain and kinetic instability. Reported here is the enantioselective synthesis of 1-sulfonylcyclopropanols, as stable yet powerful equivalents of the corresponding cyclopropanone derivatives, by α-hydroxylation of sulfonylcyclopropanes using a bis(silyl) peroxide as the electrophilic oxygen source. This work constitutes the first general approach to enantioenriched cyclopropanone derivatives. Both the electronic and steric nature of the sulfonyl moiety, which serves as a base-labile protecting group and confers crystallinity to these cyclopropanone precursors, were found to have a crucial impact on the rate of equilibration to the corresponding cyclopropanone. The utility of these cyclopropanone surrogates is demonstrated in a mild and stereospecific formal [3+1] cycloaddition with simple hydroxylamines, leading to the efficient formation of chiral β-lactam derivatives.
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.
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.
Ruthenium-Pincer-Catalyzed Hydrogenation of Lactams to Amino Alcohols
Chen, Jiangbo,Wang, Jiaquan,Tu, Tao
, p. 2559 - 2565 (2018/07/30)
By using the commercially available ruthenium pincer complex (Ru-MACHO-BH) as a catalyst, the challenging direct hydrogenation of lactams and analogues has been successfully accomplished to deliver corresponding value-added amino alcohols in good-to-excellent yields under mild reaction conditions. Remarkably, in addition to N-protected lactams, unprotected ones could also be readily reduced in the presence of a catalytic amount of weak base or even under neutral reaction conditions, which further highlights the broad substrate scope and the protocol efficiency.
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.
Catalytic hydrogenation of carboxamides and esters by well-defined Cp*Ru complexes bearing a protic amine ligand
Ito, Masato,Ootsuka, Takashi,Watari, Ryo,Shiibashi, Akira,Himizu, Akio,Ikariya, Takao
supporting information; body text, p. 4240 - 4242 (2011/06/21)
A novel catalytic method for the straightforward hydrogenation of carboxamides and esters to primary alcohols has been developed. Chiral modification in the ligand sphere of the well-defined Cp*Ru catalyst molecule opens up a new possibility for the development of an enantioselective hydrogenation of racemic substrates via dynamic kinetic resolution.
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).
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.
Efficient and regioselective synthesis of 5-hydroxy-2-isoxazolines: Versatile synthons for isoxazoles, β-lactams, and γ-amino alcohols
Tang, Shibing,He, Jinmei,Sun, Yongquan,He, Liuer,She, Xuegong
supporting information; experimental part, p. 1961 - 1966 (2010/06/20)
"Chemical Equation Presented" An efficient and highly regioselective protocol was developed for the preparation of 5-hydroxy2-isoxazolines, which have been proved to be versatile synthons for isoxazles, β-hydroxy oximes, and γ-amino alcohols. β-Lactams, commonly embedded in the skeletons of bioactive natural products, were also synthesized in two steps from β-hydroxy oximes, providing a new strategy for the synthesis of this kind of compounds.
USE OF 2-IMIDAZOLES FOR THE TREATMENT OF CNS DISORDERS
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Page/Page column 47-48, (2010/11/28)
The present invention relates to the use of compounds of formula (I) R1 is hydrogen, tritium, hydroxy, lower alkyl, lower alkoxy, halogen, nitro, amino or lower alkyl substituted by halogen; R2 is hydrogen, hydroxy or lower alkyl; X is N and Y is CH or CH2 or CH-lower alkyl or X is CH and Y is N; Q is CH2, O, NH, N-alkyl or N-SO2-alkyl or N-SO2-toluen-4-yl; W is CH2 or a bond are independently from one another 1, 2 or 3; when m is 2 or 3, R2 may m, n be the same or not; when n is 2 or 3, R1 may be the same or not; the dotted lines may each be independently from one another a bond or not; and to their pharmaceutically active salts, racemic mixtures, enantiomers, optical isomers and tautomeric forms of compounds of formula (I) for the preparation of medicaments for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.
