- Stereoselective Synthesis of Functionalized Benzooxazepino[5,4- a] isoindolone Derivatives via Cesium Carbonate Catalyzed Formal [5 + 2] Annulation of 2-(2-Hydroxyphenyl)isoindoline-1,3-dione with Allenoates
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In this work, we present a strategy for the stereoselective synthesis of functionalized benzooxazepino[5,4-a]isoindolone derivatives via a Cs2CO3-catalyzed domino β-addition and γ-aldol reaction of 2-(2-hydroxyphenyl)isoindoline-1,3-dione derivatives with allenoates, which offers an avenue for a combination of the structural unity between benzooxazepine and isoindolone motifs in synthetically useful yields with high stereoselectivities under mild conditions. Remarkably, it is the first example of highly stereoselective Cs2CO3-catalyzed formal [5 + 2] annulation of 2-(2-hydroxyphenyl)isoindoline-1,3-dione with allenoates.
- Yao, Chao,Bao, Yishu,Lu, Tao,Zhou, Qingfa
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- Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides
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We report on cyclic imides as weak directing groups for selective monohydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp2)-H bond enabling five-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp2)-H bond via larger six-membered ruthenacycle intermediates. Furthermore, monohydroxylated products were exclusively obtained (even in the presence of overstoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate coplanar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.
- Yuan, Yu-Chao,Bruneau, Christian,Dorcet, Vincent,Roisnel, Thierry,Gramage-Doria, Rafael
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p. 1898 - 1907
(2019/02/05)
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- Synthesis of novel isoindolone-based medium-sized macromolecules and triazole containing heterocyclic compounds
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A series of novel isoindolone-based macromolecules of medium-sized heterocyclic rings, such as 7,8-dihydro-6H-benzo[4,5][1,6,3]dioxazonino[2,3-a]isoindol-14(9aH)-one derivatives (5a-l), were synthesized and its frame work incorporating with a triazole moiety on phenol, ie, 2-(4-((1-(2-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)isoindoline-1,3-dione (9a-f) and also a triazole moiety on carboxylic acid, ie, (1-(2-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methyl 4-(1,3-dioxoisoindolin-2-yl)benzoate derivatives (13a-e) with various substitutions on aryl ring system have synthesized. All the synthesized compounds were characterized and confirmed with IR, 1H NMR, 13C NMR, and ESI mass spectral analysis.
- Boddu, Lingaiah,Potlapati, Varakumar,Subhashini
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p. 3197 - 3205
(2019/11/11)
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- Syntheses and characterization of nimesulide derivatives for dual enzyme inhibitors of both cyclooxygenase-1/2 and 5-lipoxygenase
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Cyclooxygenase-1/2 (COX-1/2) and 5-lipoxygenase (5-LOX) are enzymes in two different pathways in the inflammatory process. In the present study, a variety of new nimesulide derivatives were synthesized through incorporation of a 5-LOX pharmacophore into nimesulide followed with some structural modifications, which were then characterized for dual enzyme inhibitors for these two types of enzymes. Their structure-activity relationships (SARs) were studied, and compound 20f was found to be an excellent dual enzyme inhibitor. Its binding conformation and interaction mode were studied with molecular docking experiments. Compound 20f could become a lead compound for further development for potential anti-inflammatory drugs.
- Li, Yue,Chen, Shu-Han,Ou, Tian-Miao,Tan, Jia-Heng,Li, Ding,Gu, Lian-Quan,Huang, Zhi-Shu
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experimental part
p. 2074 - 2083
(2011/05/05)
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