Three-component bis-heterocycliation for synthesis of 2-aminobenzo[4,5]thieno[3,2-d]thiazoles

Organic Chemistry Frontiers, Год журнала: 2019, Номер 6(8), С. 1146 - 1150

Опубликована: Янв. 1, 2019

A cooperative base system has been developed for the novel three-component synthesis of 2-aminobenzo[4,5]thieno[3,2-d]thiazoles via bis-heterocyclization methylketoxime acetates.

Язык: Английский

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Three-Component Cascade Bis-heteroannulation of Aryl or Vinyl Methylketoxime Acetates toward Thieno[3,2-c]isoquinolines

Organic Letters, Год журнала: 2019, Номер 21(21), С. 8630 - 8634

Опубликована: Окт. 16, 2019

A three-component cascade bis-heteroannulation reaction is described that provides access to a variety of benzo[4,5]thieno[3,2-c]isoquinoline and thieno[3,2-c]isoquinoline compounds from easily available methylketoximes, o-halobenzaldehydes, elemental sulfur. Mechanistic studies reveal two-step process involving sequential copper sulfur catalysis relay.

Язык: Английский

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A review on the assembly of multi-substituted pyridines via Co-catalyzed [2 + 2 + 2] cycloaddition with nitriles

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(37), С. 7391 - 7404

Опубликована: Янв. 1, 2022

This review mainly focuses on the recent advances in Co-catalyzed [2 + 2 2] cycloaddition reaction of alkynes with nitriles to access multi-substituted pyridines. Meanwhile, brief mechanistic insights are also discussed explain observed regioselectivity.

Язык: Английский

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Diverse catalytic systems for nitrogen-heterocycle formation from O-acyl ketoximes

Chinese Chemical Letters, Год журнала: 2022, Номер 34(1), С. 107565 - 107565

Опубликована: Май 28, 2022

Язык: Английский

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Zn(II)-Catalyzed Multicomponent Sustainable Synthesis of Pyridines in Air

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(6), С. 3650 - 3665

Опубликована: Фев. 28, 2023

Herein, we report a Zn(II)-catalyzed solvent-free sustainable synthesis of tri- and tetra-substituted pyridines using alcohols as the primary feedstock NH4OAc nitrogen source. Using well-defined air-stable Zn(II)-catalyst, 1a, featuring redox-active tridentate azo-aromatic pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (La), wide variety unsymmetrical 2,4,6-substituted were prepared by three-component coupling secondary with NH4OAc. Catalyst 1a is equally compatible four-component coupling. Unsymmetrical also via alcohol two different A series up to 67% yield 1-phenylpropan-1-one or 1,2-diphenylethan-1-one The 1a-catalyzed reactions proceeded efficiently upon replacing corresponding ketones, producing desired in higher yields shorter reaction time. few control experiments performed unveil mechanistic aspects, which indicates that active participation aryl-azo ligand during catalysis enables Zn(II)-complex act an efficient catalyst for present multicomponent reactions. Aerial oxygen acts oxidant dehydrogenation alcohols, H2O H2O2 byproducts.

Язык: Английский

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Tri‐Functional Elemental Sulfur Enabling Bis‐Heteroannulation of Methyl Ketoximes with Methyl N‐Heteroarenes

Advanced Synthesis & Catalysis, Год журнала: 2018, Номер 361(3), С. 591 - 596

Опубликована: Ноя. 9, 2018

Abstract No magnified image

Язык: Английский

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Copper-Catalyzed Three-Component Domino Cyclization for the Synthesis of 4-Aryl-5-(arythio)-2-(trifluoromethyl)oxazoles

Organic Letters, Год журнала: 2019, Номер 21(21), С. 8533 - 8536

Опубликована: Окт. 11, 2019

A copper-catalyzed oxidative cyclization of oxime, arylthiol, and trifluoroacetic anhydride for the construction trisubstituted oxazoles has been developed. This transformation combines N–O bond cleavage, C–H functionalization, intramolecular annulation, providing a practical protocol introduction trifluoromethyl (−CF3) group at oxazole rings.

Язык: Английский

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Copper-Catalyzed Formal [3 + 3] Annulations of Arylketoximes and o-Fluorobenzaldehydes: An Entry to Quinoline Compounds

Organic Letters, Год журнала: 2021, Номер 23(3), С. 936 - 942

Опубликована: Янв. 14, 2021

A copper-based catalytic system has been developed to enable efficient cyclization of ketoxime acetates with o-fluorobenzaldehydes. This protocol offers an method for the synthesis substituted quinoline derivatives a broad range compatible functionalities. The present also provides rapid access synthetically and pharmaceutically useful quinoline-fused polycycles such as benzo[c]acridines.

Язык: Английский

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N-Silylenamines as Reactive Intermediates: Hydroamination for the Modular Synthesis of Selectively Substituted Pyridines

Organic Letters, Год журнала: 2018, Номер 20(21), С. 6663 - 6667

Опубликована: Окт. 23, 2018

A modular and selective synthesis of mono-, di-, tri-, tetra-, pentasubstituted pyridines is reported. Hydroamination alkynes with N-silylamine using a bis(amidate)bis(amido)titanium(IV) precatalyst furnishes the regioselective formation N-silylenamines. Addition α,β-unsaturated carbonyls to crude mixtures followed by oxidation affords 47 examples in yields up 96%. This synthetic route allows for diverse containing variable substitution patterns, including pharmaceutically relevant 2,4,5-trisubstituted pyridines, this one-pot protocol.

Язык: Английский

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Regioselectivity Control in the Oxidative Formal [3 + 2] Annulations of Ketoxime Acetates and Tetrohydroisoquinolines

Organic Letters, Год журнала: 2019, Номер 21(20), С. 8239 - 8243

Опубликована: Окт. 3, 2019

A novel copper-catalyzed oxidative formal [3 + 2] annulations of ketoxime acetates and tetrohydroisoquinolines for the synthesis fused pyrazoles imidazoles has been developed. broad range important isoquinoline-fused pyrazole imidazole products were selectively generated by key control oxidant.

Язык: Английский

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