Hypervalent Iodine Mediated Synthesis of 2-Aminobenzazoles and 2-Aminobenzothiazoles

Yi Gu; Yao Dong Li; Ye Ge; Jiang Long Huang; Hua Jin Xu; Yi Hu

doi:10.1002/ajoc.202400076

Hypervalent Iodine Mediated Synthesis of 2-Aminobenzazoles and 2-Aminobenzothiazoles

Yi Gu, Yao Dong Li, Ye Ge, Jiang Long Huang, Hua Jin Xu, Yi Hu

School of Pharmaceutical Sciences

Nanjing Tech University

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

2 Scopus citations

Abstract

The hypervalent iodine mediated, silica gel promoted synthesis of 2-aminobenzazoles and 2-aminobenzothiazole derivatives under metal-free mild conditions within short time (30 min) has been developed. Under this process, PhI(COOCF₃)₂ (PIFA) or PhI(COOCH₃)₂ (PIDA) acts as an oxidant and radical initiator direct activated the ortho-C−H bond of substrate, silica gel as weakly lewis acid effectively increased the reactivity of the reaction system. This method is compatible with various of arylurea and arylthiourea substrates, which is green, efficient, simple to operate and suitable for practical application.

Original language	English
Article number	e202400076
Journal	Asian Journal of Organic Chemistry
Volume	13
Issue number	6
DOIs	https://doi.org/10.1002/ajoc.202400076
State	Published - Jun 2024

Keywords

Arylurea
cyclization
metal-free

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10.1002/ajoc.202400076

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title = "Hypervalent Iodine Mediated Synthesis of 2-Aminobenzazoles and 2-Aminobenzothiazoles",

abstract = "The hypervalent iodine mediated, silica gel promoted synthesis of 2-aminobenzazoles and 2-aminobenzothiazole derivatives under metal-free mild conditions within short time (30 min) has been developed. Under this process, PhI(COOCF3)2 (PIFA) or PhI(COOCH3)2 (PIDA) acts as an oxidant and radical initiator direct activated the ortho-C−H bond of substrate, silica gel as weakly lewis acid effectively increased the reactivity of the reaction system. This method is compatible with various of arylurea and arylthiourea substrates, which is green, efficient, simple to operate and suitable for practical application.",

keywords = "Arylurea, cyclization, metal-free",

author = "Yi Gu and Li, {Yao Dong} and Ye Ge and Huang, {Jiang Long} and Xu, {Hua Jin} and Yi Hu",

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year = "2024",

month = jun,

doi = "10.1002/ajoc.202400076",

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T1 - Hypervalent Iodine Mediated Synthesis of 2-Aminobenzazoles and 2-Aminobenzothiazoles

AU - Gu, Yi

AU - Li, Yao Dong

AU - Ge, Ye

AU - Huang, Jiang Long

AU - Xu, Hua Jin

AU - Hu, Yi

PY - 2024/6

Y1 - 2024/6

N2 - The hypervalent iodine mediated, silica gel promoted synthesis of 2-aminobenzazoles and 2-aminobenzothiazole derivatives under metal-free mild conditions within short time (30 min) has been developed. Under this process, PhI(COOCF3)2 (PIFA) or PhI(COOCH3)2 (PIDA) acts as an oxidant and radical initiator direct activated the ortho-C−H bond of substrate, silica gel as weakly lewis acid effectively increased the reactivity of the reaction system. This method is compatible with various of arylurea and arylthiourea substrates, which is green, efficient, simple to operate and suitable for practical application.

AB - The hypervalent iodine mediated, silica gel promoted synthesis of 2-aminobenzazoles and 2-aminobenzothiazole derivatives under metal-free mild conditions within short time (30 min) has been developed. Under this process, PhI(COOCF3)2 (PIFA) or PhI(COOCH3)2 (PIDA) acts as an oxidant and radical initiator direct activated the ortho-C−H bond of substrate, silica gel as weakly lewis acid effectively increased the reactivity of the reaction system. This method is compatible with various of arylurea and arylthiourea substrates, which is green, efficient, simple to operate and suitable for practical application.

KW - Arylurea

KW - cyclization

KW - metal-free

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DO - 10.1002/ajoc.202400076

M3 - 文章

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SN - 2193-5807

VL - 13

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 6

M1 - e202400076

ER -

Hypervalent Iodine Mediated Synthesis of 2-Aminobenzazoles and 2-Aminobenzothiazoles

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Keywords

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