Synthesis of bridged bicyclic thiazine-2-thione and thiazole-2-thiones through DBU-promoted regioselective annulation of quinone monoacetals under mild conditions

Hong Qin; Man Yang; Yuguang Li; Xiaobing Yang; Yujing Hu; Chengkou Liu; Wei He; Zheng Fang; Kai Guo

doi:10.1016/j.gresc.2023.12.004

Synthesis of bridged bicyclic thiazine-2-thione and thiazole-2-thiones through DBU-promoted regioselective annulation of quinone monoacetals under mild conditions

Hong Qin, Man Yang, Yuguang Li, Xiaobing Yang, Yujing Hu, Chengkou Liu, Wei He, Zheng Fang, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

The first regioselective [4 + 2] annulation reactions of quinone monoacetals with isothiocyanates and Na₂S have been accomplished. This convenient and novel protocol involves the synthesis of valuable bridged thiazine-2-thione and thiazole-2-thiones through DBU-promoted at room temperature. Mechanism study reveals the dearomative transformation possibly undergoes a radical cascade reaction on the structure of quinone monoacetals to an efficient synthesis of a broad range of thione-containing heterocyclic compounds with broad tolerance in moderate to excellent yields. Moreover, the reported procedure can be easily applied to a 1g scale.

Original language	English
Journal	Green Synthesis and Catalysis
DOIs	https://doi.org/10.1016/j.gresc.2023.12.004
State	Accepted/In press - 2024

Keywords

Mild condition
Regioselective annulation
Thiazine-2-thiones
Thiazole-2-thiones

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10.1016/j.gresc.2023.12.004

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title = "Synthesis of bridged bicyclic thiazine-2-thione and thiazole-2-thiones through DBU-promoted regioselective annulation of quinone monoacetals under mild conditions",

abstract = "The first regioselective [4 + 2] annulation reactions of quinone monoacetals with isothiocyanates and Na2S have been accomplished. This convenient and novel protocol involves the synthesis of valuable bridged thiazine-2-thione and thiazole-2-thiones through DBU-promoted at room temperature. Mechanism study reveals the dearomative transformation possibly undergoes a radical cascade reaction on the structure of quinone monoacetals to an efficient synthesis of a broad range of thione-containing heterocyclic compounds with broad tolerance in moderate to excellent yields. Moreover, the reported procedure can be easily applied to a 1g scale.",

keywords = "Mild condition, Regioselective annulation, Thiazine-2-thiones, Thiazole-2-thiones",

author = "Hong Qin and Man Yang and Yuguang Li and Xiaobing Yang and Yujing Hu and Chengkou Liu and Wei He and Zheng Fang and Kai Guo",

note = "Publisher Copyright: {\textcopyright} 2024 Fudan University",

year = "2024",

doi = "10.1016/j.gresc.2023.12.004",

language = "英语",

journal = "Green Synthesis and Catalysis",

issn = "2666-5549",

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TY - JOUR

T1 - Synthesis of bridged bicyclic thiazine-2-thione and thiazole-2-thiones through DBU-promoted regioselective annulation of quinone monoacetals under mild conditions

AU - Qin, Hong

AU - Yang, Man

AU - Li, Yuguang

AU - Yang, Xiaobing

AU - Hu, Yujing

AU - Liu, Chengkou

AU - He, Wei

AU - Fang, Zheng

AU - Guo, Kai

PY - 2024

Y1 - 2024

N2 - The first regioselective [4 + 2] annulation reactions of quinone monoacetals with isothiocyanates and Na2S have been accomplished. This convenient and novel protocol involves the synthesis of valuable bridged thiazine-2-thione and thiazole-2-thiones through DBU-promoted at room temperature. Mechanism study reveals the dearomative transformation possibly undergoes a radical cascade reaction on the structure of quinone monoacetals to an efficient synthesis of a broad range of thione-containing heterocyclic compounds with broad tolerance in moderate to excellent yields. Moreover, the reported procedure can be easily applied to a 1g scale.

AB - The first regioselective [4 + 2] annulation reactions of quinone monoacetals with isothiocyanates and Na2S have been accomplished. This convenient and novel protocol involves the synthesis of valuable bridged thiazine-2-thione and thiazole-2-thiones through DBU-promoted at room temperature. Mechanism study reveals the dearomative transformation possibly undergoes a radical cascade reaction on the structure of quinone monoacetals to an efficient synthesis of a broad range of thione-containing heterocyclic compounds with broad tolerance in moderate to excellent yields. Moreover, the reported procedure can be easily applied to a 1g scale.

KW - Mild condition

KW - Regioselective annulation

KW - Thiazine-2-thiones

KW - Thiazole-2-thiones

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U2 - 10.1016/j.gresc.2023.12.004

DO - 10.1016/j.gresc.2023.12.004

M3 - 文章

AN - SCOPUS:85189680308

SN - 2666-5549

JO - Green Synthesis and Catalysis

JF - Green Synthesis and Catalysis

ER -

Synthesis of bridged bicyclic thiazine-2-thione and thiazole-2-thiones through DBU-promoted regioselective annulation of quinone monoacetals under mild conditions

Abstract

Keywords

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