Reactivity of ynamides in catalytic intermolecular annulations

Chemical Society Reviews, Journal Year: 2020, Volume and Issue: 50(4), P. 2582 - 2625

Published: Dec. 24, 2020

This review comprehensively summarizes the advances achieved in catalytic intermolecular annulations of ynamides from 2010 to 2020.

Language: Английский

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Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Synthesis, Journal Year: 2021, Volume and Issue: 54(01), P. 4 - 32

Published: Sept. 27, 2021

Abstract Metal-catalyzed [2+2+2] cycloaddition is a powerful tool that allows rapid construction of functionalized 6-membered carbo- and heterocycles in single step through an atom-economical process with high functional group tolerance. The reaction usually regio- chemoselective although selectivity issues can still be challenging for intermolecular reactions involving the cross-[2+2+2] two or three different alkynes various strategies have been developed to attain selectivities. Furthermore, enantioselective efficient means create central, axial, planar chirality variety chiral organometallic complexes used asymmetric transition-metal-catalyzed inter- intramolecular reactions. This review summarizes recent advances field cycloaddition. 1 Introduction 2 Formation Carbocycles 2.1 Intermolecular Reactions 2.1.1 Cyclotrimerization Alkynes 2.1.2 Cycloaddition Two Different 2.1.3 Alkynes/Alkenes Alkenes/Enamides 2.2 Partially Intramolecular 2.2.1 Rhodium-Catalyzed 2.2.2 Molybdenum-Catalyzed 2.2.3 Cobalt-Catalyzed 2.2.4 Ruthenium-Catalyzed 2.2.5 Other Metal-Catalyzed 2.3 Totally 3 Heterocycles 3.1 Nitriles 3.2 1,6-Diynes Cyanamides 3.3 Selenocyanates 3.4 Imines Allenes Alkenes 3.5 (Thio)Cyanates Isocyanates 3.6 1,3,5-Triazines 3.7 Aldehydes Enynes Allenes/Alkenes 3.8 4 Conclusion

Language: Английский

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Atom-economic synthesis of β-ketosulfones based on gold-catalyzed highly regioselective hydration of alkynylsulfones

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(8), P. 3314 - 3320

Published: Jan. 1, 2022

Gold( i )-catalyzed highly regioselective hydration of alkynylsulfones comprises an efficient 100% atom-economic route to β-ketosulfones.

Language: Английский

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Modular approach to non-aromatic and aromatic pyrroles through gold-catalyzed [3 + 2] cycloaddition of 2H-azirines and ynamides

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(19), P. 5133 - 5140

Published: Jan. 1, 2022

The developed modular approach to hard-to-reach non-aromatic 3 H - and 2 -pyrroles is based on the integration of -azirines ynamides.

Language: Английский

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Neighboring group-directed asymmetric [2 + 2 + 2] cycloaddition to access C–N axially chiral indoles

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2857 - 2863

Published: Jan. 1, 2024

A Rh-catalyzed neighboring group-directed asymmetric [2 + 2 2] cycloaddition of 1,6-diynes and ynamides to generate C–N axially chiral indole derivatives has been developed.

Language: Английский

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Oxygen Atom Transfer as Key To Reverse Regioselectivity in the Gold(I)-Catalyzed Generation of Aminooxazoles from Ynamides

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 86(2), P. 1748 - 1757

Published: Dec. 28, 2020

We report on gold(I)-catalyzed oxidative annulation involving ynamides, nitriles, and 2,3-dichloropyridine N-oxide. The application of N-oxide as an oxygen atom transfer reagent reverses the regioselectivity to give 5-amino-1,3-oxazoles, in comparison with previously reported syntheses aminooxazoles based gold-catalyzed nitrene transfers ynamides furnish 4-amino-1,3-oxazoles. developed approach allows generation 1,3-oxazoles containing a variety sulfonyl-protected alkylamino groups fifth position oxazole ring (29 examples; up 88% yields). In addition, use N-substituted namely cyanamides, leads facile difficult-to-obtain 2,5-diaminooxazoles. process is feasible for wide ranges or it can be conducted gram scale.

Language: Английский

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Annulations of Ynamides with 1,2-Benzisothiazoles to Construct 1,4-Benzothiazepines and 3-Aminoisoquinolines

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1522 - 1527

Published: Feb. 13, 2024

Two distinct TMSOTf-catalyzed annulation reactions between ynamides and 1,2-benzisothiazoles have been developed. The direction of the reaction could be easily switched by applying different thermodynamic-controlled conditions. At room temperature, undergo a [5 + 2] with to afford 1,4-benzothiazepines, whereas under heating conditions desulfurizative proceeds well access 3-aminoisoquinolines. These two protocols provide biologically important 1,4-benzothiazepines 3-aminoisoquinolines high efficiency broad substrate scopes mild

Language: Английский

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[2+2+2] Cycloadditions

Elsevier eBooks, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

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TMSOTf/TfOH-Promoted [4 + 2] Annulation of Ynamides with 2-Aminoarylnitriles To Construct 2,4-Diaminoquinolines

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 9, 2025

An effective strategy to synthesize 2,4-diaminoquinoline compounds has been efficaciously developed via a TMSOTf/TfOH-promoted [4 + 2] annulation of ynamides with 2-aminoarylnitriles. Compared the reported transition-metal catalysts, this metal-free promotion system presented remarkable advancement, enabling facile and regiospecific assembly frameworks wide functional group compatibility moderate excellent yields.

Language: Английский

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Gold‐Catalyzed Alkyne‐Amine Cascade Annulations: A Modern Strategy for Azaheterocycle Construction

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: April 7, 2025

Abstract Gold catalysis has experienced remarkable progress over the past two decades, particularly in transformations involving alkynes. While numerous aspects of gold‐catalyzed reactions have been extensively reviewed, specific area cascade annulations between functionalized amines and alkynes represents a distinct rapidly developing direction that warrants focused attention. This survey collects systematically analyzes these transformations, which emerged as convenient synthetic strategies to diverse nitrogen heterocycles. The relevant are classified firstly by chemical nature amine functional substituent, secondly size formed ring. field under consideration bridges several fundamental practical branches chemistry, including catalysis, organic synthesis, medicinal materials science.

Language: Английский

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