Facile synthesis of 3-aryl 2,3-dihydrobenzofurans via novel domino 1,6-addition/O-alkylation reactions of para-quinone methides

Tetrahedron, Journal Year: 2018, Volume and Issue: 74(13), P. 1492 - 1496

Published: Feb. 3, 2018

Language: Английский

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Base-catalyzed controllable reaction of 3-ylideneoxindoles with O-Boc hydroxycarbamates for the synthesis of amidoacrylates and spiroaziridine oxindoles

Organic & Biomolecular Chemistry, Journal Year: 2016, Volume and Issue: 14(23), P. 5224 - 5228

Published: Jan. 1, 2016

A base-catalyzed divergent reaction of 3-ylideneoxindoles with O-Boc hydroxycarbamates has been developed to provide efficient access various amidoacrylates and spiroaziridine oxindoles generally high yields, which should be potentially useful in drug discovery.

Language: Английский

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High diastereoselective synthesis of spiro-isoxazolonechromans via domino oxa-Michael/1,6-addition reactions of ortho-hydroxyphenylsubstituted para-quinone methides with unsaturated isoxazolones

Tetrahedron, Journal Year: 2018, Volume and Issue: 75(5), P. 682 - 687

Published: Dec. 29, 2018

Language: Английский

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Diversity Oriented Synthesis of Indoloazepinobenzimidazole and Benzimidazotriazolobenzodiazepine from N¹‐Alkyne‐1,2‐diamines

Chemistry - A European Journal, Journal Year: 2015, Volume and Issue: 21(51), P. 18828 - 18833

Published: Nov. 3, 2015

Abstract A one‐pot protocol for the diversity oriented synthesis of two N ‐polyheterocycles indoloazepinobenzimidazole and benzimidazotriazolobenzodiazepine from a common 1 ‐alkyne‐1,2‐diamine building block is described. The approach involves sequential formation benzimidazole through cyclocondensation oxidation, which followed by either an azepine ring (through alkyne activation 6‐ endo‐dig cyclization, 1,2‐migration with expansion, re‐aromatization), or diazepine triazole rings 1,3‐dipolar cycloaddition.

Language: Английский

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Diastereoselective construction of pyrrolo[2,1-a]isoquinoline-based bispirooxindoles through a three-component [3 + 2] cycloaddition

Organic & Biomolecular Chemistry, Journal Year: 2018, Volume and Issue: 16(33), P. 6025 - 6034

Published: Jan. 1, 2018

An efficient three-component one-pot [3 + 2] cycloaddition of isatins, 1,2,3,4-tetrahydroisoquinolines and methyleneindolinones has been developed. This reaction proceeded in a highly diastereoselective manner to afford wide range pyrrolo[1,2-a]isoquinoline-based bispirooxindoles up 91% yields. Additionally, gram-scale experiment some chemical transformations were conducted.

Language: Английский

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Construction of bridged cyclic N,O-ketal spirooxindoles through a Michael addition/N,O-ketalization sequence

Organic & Biomolecular Chemistry, Journal Year: 2018, Volume and Issue: 16(10), P. 1751 - 1759

Published: Jan. 1, 2018

The first highly diastereoselective TfOH-catalyzed Michael addition/N,O-ketalization sequence of 3-aminooxindoles and ortho-hydroxychalcones was achieved, delivering a wide range bridged cyclic N,O-ketal spirooxindoles with complex strained structures in 41-97% yields. Moreover, gram-scale experiment some chemical conversions were conducted to further demonstrate the synthetic value.

Language: Английский

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An Effective Method for the Synthesis of 1,3‐Dihydro‐2H‐indazoles via N‐N Bond Formation

Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 361(24), P. 5552 - 5557

Published: Oct. 25, 2019

Abstract The [4+1] cycloaddition reaction of bifunctional amino reagents has been achieved with in situ formed aza‐ ortho ‐quinone methides. Specifically, N ‐(tosyloxy)carbamates were used as an N1 synthon and for this transformation, which provides a metal‐free, catalyst‐free, oxidant‐free strategy to form nitrogen‐nitrogen bonds. magnified image

Language: Английский

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A copper-catalyzed tandem reaction for the construction of coumarin fused 9H-pyrrolo[1,2-a]indoles

Organic & Biomolecular Chemistry, Journal Year: 2017, Volume and Issue: 15(41), P. 8729 - 8737

Published: Jan. 1, 2017

An efficient copper-catalyzed Friedel–Crafts alkylation/cyclization/isomerization sequence of 3-arylcarbonyl coumarins and 3-methyl indole was developed to afford a wide range functionalized coumarin fused 9H-pyrrolo[1,2-a]indoles with 6-6-5-5-6 pentacyclic core.

Language: Английский

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A FeCl₃-catalyzed highly regioselective 1,2-addition/substitution sequence for the construction of coumarin-substituted bis(indolyl)methanes

Organic & Biomolecular Chemistry, Journal Year: 2016, Volume and Issue: 14(19), P. 4420 - 4425

Published: Jan. 1, 2016

A FeCl3-catalyzed highly regioselective 1,2-addition/substitution sequence of 3-acetylcoumarins and indoles has been developed to afford hindered tetrasubstituted bis(indolyl)methanes bearing a biologically useful coumarin motif in 56-99% yields.

Language: Английский

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One‐pot and Environmentally Friendly Synthesis of New Spiroindolones Using Functionalized Multiwall Carbon Nanotubes as Powerful Catalyst

Journal of the Chinese Chemical Society, Journal Year: 2016, Volume and Issue: 63(5), P. 399 - 403

Published: April 5, 2016

Abstract Multiwall carbon nanotubes were functionalized and then used as powerful nanocatalyst for the one‐pot, three‐component synthesis of new spiroindolones. Functionalized multiwall (FMWCNTs) showed a good catalytic ability recyclability in current reaction. The present strategy offers some interesting advantages such simplicity, high yields products, non‐toxic nature.

Language: Английский

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