Metal-free transfer hydrogenation/cycloaddition cascade of activated quinolines and isoquinolines with tosyl azides DOI
Suman Yadav,

Ruchir Kant,

Malleswara Rao Kuram

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(46), P. 7088 - 7091

Published: Jan. 1, 2023

The difficulty in isolating cyclic enamines emanating from their intrinsic instability has impeded exploration cycloaddition reactions. Here, we achieved a metal-free domino reaction providing quinoline and isoquinoline-derived amidines by the of azides with situ generated via dearomatization.

Language: Английский

1,7-Hydride transfer-involved dearomatization of quinolines to access C3-spiro hydroquinolines DOI Creative Commons

Da-Ying Shao,

Bin Qiu,

Zi-Kang Wang

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Feb. 1, 2024

1,7-Hydride transfer-involved dearomatization of quinolines toward C3-spiro hydroquinoline derivatives has been developed. This method offers a protocol to achieve the electron-deficient arenes via redox-neutral hydride transfer process. A series hydroquinolines can be provided in moderate excellent yields (up 98%) with good diastereoselectivities. Significant advantages such as high step- and atom-economy, well mild conditions, make it an appealing alternative quinolines.

Language: Английский

Citations

2
Stable Meisenheimer Complexes as Powerful Photoreductants Readily Obtained from Aza‐Heteroaromatic Compounds DOI Creative Commons
Francesco Calogero,

Leonie Wilczek,

Emanuele Pinosa

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(44)

Published: July 30, 2024

Abstract Excited states of radical anions derived from the photoreduction stable organic molecules are suggested to serve as potent reductants. However, excited these species too short‐lived allow bimolecular quenching processes. Recently, singlet state Meisenheimer complexes, which possess a long‐lived state, was identified competent for reduction challenging substrates (−2.63 V vs. SCE, saturated calomel electrode). To produce reasonably and simply accessible different addition n BuLi readily available aromatic heterocycles investigated, photoreactivity generated studied. In this paper, we present straightforward preparation family powerful photoreductants (*E ox < −3 SCE in their states, determined by DFT time‐dependent TD‐DFT calculations; DFT, density functional theory) that can induce dehalogenation electron‐rich aryl chlorides form C−C bond through cyclization. Photophysical analyses computational studies combination with experimental mechanistic investigations demonstrate ability adduct act strong electron donor under visible light irradiation.

Language: Английский

Citations

2
A Modular Approach for Accessing 3D Heterocycles via 1,2‐Dicyanation of Planar N‐Heteroarenes DOI
Sukumar Pradhan,

Sudip Maiti,

Suparna Dutta

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 64(1)

Published: Sept. 16, 2024

The rapid construction of three-dimensional (3D) heterocyclic frameworks is a key challenge in contemporary medicinal chemistry. molecules with complexity hold greater probability to improve clinical outcomes, solubility, selectivity for target proteins, and metabolic stability. However, the prevalence flat persists among new drug candidates, primarily owing multitude chemical methods available their synthesis. In principle, dearomative functionalization N-heteroarene allows conversion readily planar into partially or fully saturated nitrogen heterocycles, which are most significant structural motifs pharmaceuticals natural products. Unfortunately, these reactions very rare because inherent imposed by heteroarenes' poor reactivity, rendering process thermodynamically unfavorable. Herein, we report modular approach accessing 3D space translating heteroarenes valuable heterocycles via installation highly versatile cyano group as vector. This enabled situ generation reactive, non-symmetric iodane combining cyanide anion bench-stable PhI(OAc)

Language: Английский

Citations

2
Reductive Coupling of N-Heteroarenes and 1,2-Dicarbonyls for Direct Access to γ-Amino Acids, Esters, and Ketones Using a Heterogeneous Single-Atom Iridium Catalyst DOI
Huanhuan Jia, Qi Liao, Wei Liu

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(46), P. 31647 - 31655

Published: Nov. 7, 2024

Despite their significant importance, the challenges in direct and diverse synthesis of N-heterocyclic γ-amino acids/esters/ketones hamper exploration applications. Herein, by developing a multifunctional heterogeneous iridium single-atom catalyst composed silica-confined species boron-doped ZrO

Language: Английский

Citations

2
Metal-free transfer hydrogenation/cycloaddition cascade of activated quinolines and isoquinolines with tosyl azides DOI
Suman Yadav,

Ruchir Kant,

Malleswara Rao Kuram

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(46), P. 7088 - 7091

Published: Jan. 1, 2023

The difficulty in isolating cyclic enamines emanating from their intrinsic instability has impeded exploration cycloaddition reactions. Here, we achieved a metal-free domino reaction providing quinoline and isoquinoline-derived amidines by the of azides with situ generated via dearomatization.

Language: Английский

Citations

5