117516-63-9Relevant academic research and scientific papers
Regioselective tandem dimethylsulfonium methylide addition - Eliminative olefination of diendioates: A novel route to 1,3-butadien-2-ylmalonates
Singh, Rekha,Ghosh, Sunil K.
, p. 5071 - 5074 (2007)
The appropriate choice of dimethylsulfonium methylide generation conditions enables the highly regioselective tandem ylide addition-eliminative olefination to 1,3-dienedioates providing 1,3-butadien-2-ylmalonates, a novel class of 2-substituted 1,3-dienes suitable for quick assembly of precursors for type 2 intramolecular Diels-Alder reactions.
Dioxazolones as masked ester surrogates in the Pd(ii)-catalyzed direct C-H arylation of 6,5-fused heterocycles
Saxena, Paridhi,Maida, Neha,Kapur, Manmohan
supporting information, p. 11187 - 11190 (2019/09/30)
A simple and effective Pd(ii)-catalyzed regioselective C(2)-H arylation of 6,5-fused heterocycles with dioxazolones as a masked ester surrogate under mild conditions is reported. The significance of the arylation is highlighted by the new reactivity demonstrated in dioxazolones via proximal C-H activation of the cyclic carbonate of the hydroxamic acid functionality under protic conditions.
Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N′-Acyl Arylhydrazines
Cao, Jun,Chen, Zi-Li,Li, Shu-Min,Zhu, Gao-Feng,Yang, Yuan-Yong,Wang, Cong,Chen, Wen-Zhang,Wang, Jian-Ta,Zhang, Ji-Quan,Tang, Lei
supporting information, p. 2774 - 2779 (2018/06/21)
A novel ligand-free palladium-catalyzed C-2 arylation of benzofurans has been developed using N′-acyl arylhydrazines as the coupling partners and TEMPO as an oxidant. This protocol features a wide functional-group tolerance and highly regioselective products with good to excellent yields.
OXADIAZINE COMPOUNDS AND METHODS OF USE THEREOF
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Paragraph 0187, (2016/12/26)
The present disclosure relates to oxadiazine compounds, pharmaceutical compositions comprising an effective amount of an oxadiazine compound and methods for using an oxadiazine compound in the treatment of a neurodegenerative disease, comprising administering to a subject in need thereof an effective amount of an oxadiazine compound.
Palladium-Catalyzed Dearomatizing Difunctionalization of Indoles and Benzofurans
Ramella, Vincenzo,He, Zhiheng,Daniliuc, Constantin G.,Studer, Armido
supporting information, p. 2268 - 2273 (2016/05/19)
A palladium-catalyzed dearomatizing difunctionalization of N-Boc-indoles and benzofurans to give tricyclic indolines and 2,3-dihydrobenzofurans with a fully substituted carbon center is described. Product formation occurs under mild conditions at room temperature with commercially available aryl boronic acids and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) as a mild oxidant in good yields. 2-Carboxyalkyl-substituted indoles and benzofurans react under Pd-catalysis with aryl boronic acids and TEMPO through dearomatizing arylation/cyclization to the corresponding indolines and dihydrobenzofurans containing a lactone moiety bearing a fully substituted carbon center.
A Pincer Ruthenium Complex for Regioselective C-H Silylation of Heteroarenes
Fang, Huaquan,Guo, Le,Zhang, Yuxuan,Yao, Wubing,Huang, Zheng
supporting information, p. 5624 - 5627 (2016/11/17)
A pincer Ru(II) catalyst for the highly efficient undirected silylation of O- and S-heteroarenes with (TMSO)2MeSiH and Et3SiH is described, producing heteroarylsilanes with exclusive C2-regioselectivity, good functional-group tolerance, and high turnover numbers (up to 1960). The synthetic utility of the silylated products is demonstrated by Pd-catalyzed Hiyama-Denmark cross-coupling under mild conditions. One-pot, two-step silylation and coupling procedures have been also developed.
A dimethylsulfonium methylide mediated highly regioselective olefination of conjugated polyolefin 1,1-dioates to conjugated polyene-2-yl-malonates and their applications in Diels-Alder reactions
Singh, Rekha,Ghosh, Sunil K.
supporting information; experimental part, p. 2284 - 2292 (2010/06/16)
The reactions between dimethylsulfonium methylide and 1,3-diene- or 1,3,5-triene-1,1-dioates under specific conditions enable the highly regioselective tandem ylide addition-eliminative olefination to provide 1,3-butadien-2-yl- or 1,3,5-hexatriene-2-yl-malonates. Alkylation at malonate methine carbon of 1,3-butadien-2-ylmalonates with a suitable alkyl halide having in-built functionalities for a dienophile generation led to quick assembly of precursors for type 2 intramolecular Diels-Alder reaction. Syntheses of functionalized bicyclo[n.3.1] alkenes (n=5 or 6) with the double bond at the bridgehead position have been achieved via the IMDA. An asymmetric version of this reaction has been developed using a MacMillan's imidazolidinone catalyst, which provided a bicyclo[5.3.1] alkene with very high enantioselectivity. In situ methylation at malonate methine carbon of 1,3,5-hexatriene-2-yl-malonates followed by intermolecular Diels-Alder reaction with N-methylmaleimide provided the cycloadduct with complete regiocontrol and high diastereoselectivity.
Discovery of novel and potent retinoic acid receptor α agonists: Syntheses and evaluation of benzofuranyl-pyrrole and benzothiophenyl-pyrrole derivatives
Yoshimura, Hiroyuki,Kikuchi, Kouichi,Hibi, Shigeki,Tagami, Katsuya,Satoh, Takashi,Yamauchi, Toshihiko,Ishibahi, Akira,Tai, Kenji,Hida, Takayuki,Tokuhara, Naoki,Nagai, Mitsuo
, p. 2929 - 2937 (2007/10/03)
In the course of our studies on retinoic acid receptor (RAR) agonists, we have designed and synthesized a series of benzofuran and benzothiophene derivatives. Some of these compounds (1a,b,e,f,j) markedly inhibited LPS- induced B-lymphocyte proliferation and exerted RARα selectivity. One of them, 4-[5-(4,7-dimethylbenzofuran-2-yl)pyrrol-2-yl]benzoic acid (1b), when orally administered significantly inhibited mouse antibody production and delayed type hypersensitivity (DTH) responses from a dose of 0.1 mg/kg.
N-Acyl-2-substituted-1,3-thiazolidines, a New Class of Non-narcotic Antitussive Agents: Studies Leading to the Discovery of Ethyl 2--β-oxothiazolidine-3-propanoate
Gandolfi, Carmelo A.,Domenico, Roberto Di,Spinelli, Silvano,Gallico, Licia,Fiocchi, Luigi,et al.
, p. 508 - 525 (2007/10/02)
The synthesis of a novel class of antitussive agents is described.The compounds were examined for antitussive activity in guinea pig after cough induction by electrical or chemical stimulation.Ethyl 2--β-oxothiazolidine-3-propanoate (BBR 2173, moguisteine, 7) and other structurally related compounds showed a significant level of activity, comparable to that of codeine and dextromethorphan.The compounds presented in this paper are characterized by the N-acyl-2-substituted-1,3-thiazolidine moiety, which is a novel entry in the field of antitussive agents.The serendipitous discovery of the role played by the thiazolidine moiety in the determining the antitussive effect promoted extensive investigations on these structures.This optimization process on N-acyl-2-substituted-1,3-thiazolidines led to the initial identification of 2--3--1,3-thiazolidine (18a) as an interesting lead compound.The careful study of the rapid and very complicated metabolism of 18a provided further insights for the design of newer related derivatives.The observation that the metabolic oxidation on the lateral chain's sulfur of 18a to sulfoxide maintained the antitussive properties suggested the introduction of isosteric functional groups with respect to the sulfoxide moiety.Subsequent structural modifications showed that hydrolyzable malonic residues in the 3-position of the thiazolidine ring were able to assure high antitussive activity.This optimization ultimately led to the selection of moguisteine (7) as the most effective and safest representative of the series.Moguisteine is completely devoid of unwanted side effects (such as sedation and addiction), and its activity was demonstrated also in clinical studies.
PREPARATION AND CYCLIZATION OF ARYLOXYACETALDEHYDE ACETALS; A GENERAL SYNTHESIS OF 2,3-UNSUBSTITUTED BENZOFURANS
Barker, Peter,Finke, Paul,Thompson, Kevan
, p. 257 - 266 (2007/10/02)
A improved method for the preparation of 2,3-unsubstituted benzofurans is described.Specifically, the PPA catalysed cyclization of aryloxyacetaldehyde acetals to give (4-7)-substituted benzofurans has been achieved.
