1,5-Hydrogen atom transfer of α-iminyl radical cations: a new platform for relay annulation for pyridine derivatives and axially chiral heterobiaryls

Zhou, Yu-Qiang; He, Kui-Cheng; Zheng, Wei-Hao; Lv, Jing-Fang; He, Shi-Mei; Yu, Ning; Yang, Yun-Bo; Liu, Lv-Yan; Jiang, Kun; Wei, Ye

doi:10.1039/d4sc01858c

Chem. Sci.

2024

DOI: 10.1039/d4sc01858c

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1,5-Hydrogen atom transfer of α-iminyl radical cations: a new platform for relay annulation for pyridine derivatives and axially chiral heterobiaryls

Yu-Qiang Zhou,

Kui-Cheng He,

Wei-Hao Zheng

et al.

Abstract: The exploitation of new reactive species and novel transformation modes for their synthetic applications have significantly promoted the development of synthetic organic methodology, drug discovery, and advanced functional materials. α-Iminyl...

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Cited by 4 publications

References 77 publications

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NaOAc-Promoted [3+1+2] Annulation of O-Pivaloyl Oximes, Aldehydes, and 2-Methylbenzothiazole Salts: Synthesis of 1-Azaphenothiazines

Liang,

Cai,

et al. 2024

J. Org. Chem.

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This paper presents an efficient strategy for constructing 1-azaphenothiazines through the NaOAc-promoted [3+1+2] annulation of O-pivaloyl oximes, aldehydes, and 2-methylbenzothiazole salts. The reaction is conducted in ethanol and employs oxygen as the oxidant under catalyst-free conditions. The process is amenable to various O-pivaloyl oximes, 2-methylbenzothiazole salts, and aldehydes, affording the target products in satisfactory yields.

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NaOAc-Promoted [3+1+2] Annulation of O-Pivaloyl Oximes, Aldehydes, and 2-Methylbenzothiazole Salts: Synthesis of 1-Azaphenothiazines

Liang,

Cai,

et al. 2024

J. Org. Chem.

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Iron-Catalyzed One-Pot Cascade Reactions of Oximes with Inactivated Saturated Ketones: Entry to Highly Substituted Pyridines

Liu,

Zhai

2024

J. Org. Chem.

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An iron-catalyzed oxidative [3 + 3] annulation of oxime esters with inactivated saturated ketones is described. This cascade strategy allows one-step rapid synthesis of various structurally important pyridines through an oxidative dehydrogenation/ annulation/oxidative aromatization sequence via direct α,β-dehydrogenation of simple saturated ketones followed by annulation with oximes. This method shows good functional group tolerance, readily accessible starting materials, a wide substrate scope, high chemoselectivity, and no need for extra stoichiometric oxidant and is also applicable to the late-stage functionalization of natural products.

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The Construction of Furocoumarins through Iron-Catalyzed Relay Annulation of Oxime Esters with 4-Hydroxycoumarins

Jiang,

Liu,

Zhou

et al. 2024

Org. Lett.

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An iron-catalyzed relay annulation protocol was disclosed, which utilizes oxime esters and 4-hydroxycoumarins as the readily available starting materials and showcases broad substrate scope and good functional group tolerance. This method allows the simultaneous generation of two C–C and one C–O bonds and two rings in one step, affording structurally new furocoumarins in moderate to good yields.

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1,5-Hydrogen atom transfer of α-iminyl radical cations: a new platform for relay annulation for pyridine derivatives and axially chiral heterobiaryls

Abstract: The exploitation of new reactive species and novel transformation modes for their synthetic applications have significantly promoted the development of synthetic organic methodology, drug discovery, and advanced functional materials. α-Iminyl...

Cited by 4 publications

References 77 publications

NaOAc-Promoted [3+1+2] Annulation of O-Pivaloyl Oximes, Aldehydes, and 2-Methylbenzothiazole Salts: Synthesis of 1-Azaphenothiazines

NaOAc-Promoted [3+1+2] Annulation of O-Pivaloyl Oximes, Aldehydes, and 2-Methylbenzothiazole Salts: Synthesis of 1-Azaphenothiazines

Iron-Catalyzed One-Pot Cascade Reactions of Oximes with Inactivated Saturated Ketones: Entry to Highly Substituted Pyridines

The Construction of Furocoumarins through Iron-Catalyzed Relay Annulation of Oxime Esters with 4-Hydroxycoumarins

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