40132-01-2Relevant articles and documents
Transition-Metal-Free Ring-Opening Reaction of 2-Halocyclobutanols through Ring Contraction
Oeser, Petr,Edlová, Tereza,?ubiňák, Marek,Tobrman, Tomá?
, p. 4958 - 4967 (2021/09/28)
The present work describes the preparation of halohydrins from 2-halocyclobutanones by means of reactions with Grignard reagents at ?78 °C. We discovered that the prepared cyclobutanols underwent a thermal ring-opening reaction. Depending on the structure of the starting cyclobutanol, different products were formed. More specifically, 1-substituted 2-bromocyclobutan-1-ol was found to open to γ-substituted butyrophenones. A novel 1,3-dihydro-2H-inden-2-ylidene derivative was obtained for indene-derived cyclobutanols. Based on the outcomes of the performed experiments, a mechanism for the ring-opening of cyclobutanols can be proposed.
Intramolecular Cyclization of Brominated Oxime Ether Promoted with Ytterbium(0) to the Synthesis of Cyclic Imines
Wang, Yiqiong,Huang, Fei,Zhang, Songlin
supporting information, p. 5178 - 5181 (2020/08/13)
The first utility of ytterbium(0) as a mediating-metal in the intramolecular cyclization of brominated oxime ether was reported in this paper. In contrast to the prior methods, the N–O bond was used as a receptor of nucleophilic reagent, rather than as a source of N-centered radicals. Cyclic imines were obtained in this one-pot reaction with a broad scope of substrates and feasible reaction conditions.
Light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds
Fu, Hua,Liu, Can,Liu, Yong,Yang, Haijun,Zhu, Xianjin
supporting information, p. 4357 - 4363 (2020/07/14)
Visible light-induced organic reactions are important chemical transformations in organic chemistry, and their efficiency highly depends on suitable photocatalysts. However, the commonly used photocatalysts are precious transition-metal complexes and elaborate organic dyes, which hamper large-scale production due to high cost. Here, for the first time, we report a novel strategy: light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds, allowing high-value-added aromatic ketones and carboxylic acids to be easily prepared in high-to-excellent yields using readily available alkyl arenes, methyl arenes and aldehydes as materials. The mechanistic investigations showed that the treatment of inexpensive and readily available sodium trifluoromethanesulfinate with oxygen under irradiation of light could in situ form a pentacoordinate sulfide intermediate as an efficient photosensitizer. The method represents a highly efficient, economical and environmentally friendly strategy, and the light and oxygen-enabled sodium trifluoromethanesulfinate photocatalytic system represents a breakthrough in photochemistry. This journal is
Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines
Huang, Fei,Zhang, Songlin
supporting information, p. 7430 - 7434 (2019/10/11)
A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.
Visible-light-enhanced ring opening of cycloalkanols enabled by br?nsted base-tethered acyloxy radical induced hydrogen atom transfer-electron transfer
Zhao, Rong,Yao, Yuan,Zhu, Dan,Chang, Denghu,Liu, Yang,Shi, Lei
supporting information, p. 1228 - 1231 (2018/02/23)
A metal-free ring opening/halogenation of cycloalkanols, which combines both PPO/TBAX oxidant system and blue LEDs irradiation, is presented. This method produces diverse γ, α, and even more remotely halogenated ketones in moderate to excellent yields under mild conditions. Interestingly, experimental and computational studies demonstrate the novel ring size-dependent concerted/stepwise (four-/five- to eight-membered rings) hydrogen atom transfer-electron transfer induced by Br?nsted base-tethered acyloxy radical, which indicates distinct advantages brought by the cyclic structure of diacyl peroxides.
Novel compound capable of activating Nrf2, and pharmaceutical compositions comprising the same
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Paragraph 1142; 1232-1234, (2016/10/08)
The present invention provides a novel compound which can activate Nrf2 that is a transcription factor for expression of the quinone reductase gene. Therefore the compound is effective for inhibiting apoptosis and preventing and treating brain nerve disea
Synthesis and Nrf2 activating ability of thiourea and vinyl sulfoxide derivatives
Shim, Young Sun,Hwang, Hyun Sook,Nam, Ghilsoo,Choi, Kyung Il
, p. 2317 - 2320 (2013/09/24)
Thiourea and vinyl sulfoxide derivatives were designed based on the structures of sulforaphane and gallic acid, prepared and tested for HO-1 inducing activity as a measure of Nrf2 activation, and inhibitory effect on NO production as a measure of anti-inf
Synthesis of γ-halogenated ketones via the Ce(IV)-mediated oxidative coupling of cyclobutanols and inorganic halides
Casey, Brian M.,Eakin, Cynthia A.,Flowers II, Robert A.
body text, p. 1264 - 1266 (2009/09/05)
A straightforward method for the synthesis of γ-halo-substituted ketones formed via the CAN-initiated oxidative addition of halides to 1-substituted cyclobutanols has been developed. This method has short reaction times, and provides access to a range of bromo and iodo γ-substituted ketones in good to excellent yields.
9-(Arylalkyl or aroylalkyl)-1-oxa-4,9-diazaspiro(5.5)undecan-3-ones
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, (2008/06/13)
Compounds useful in the prevention and/or treatment of hypertension, congestive heart failure, arrhythmia, migraine, vasospastic disorders, and asthma are represented by the formula STR1 wherein: R1 is STR2 wherein X is hydrogen, lower alkyl, lower alkoxy, halo, carboxamido or hydroxy; m is 1, 2 or 3; and n is 1, 2 or 3; R2, R3 and R4 are independently hydrogen or lower alkyl; and the pharmaceutically acceptable acid addition salts thereof.