Photomediated Spirocyclization of N-Benzyl Propiolamide with N-Iodosuccinimide for Access to Azaspiro[4.5]deca-6,9-diene-3,8-dione

Man Yang; Jiawei Hua; Hao Wang; Tao Ma; Chengkou Liu; Wei He; Ning Zhu; Yujing Hu; Zheng Fang; Kai Guo

doi:10.1021/acs.joc.2c00579

Photomediated Spirocyclization of N-Benzyl Propiolamide with N-Iodosuccinimide for Access to Azaspiro[4.5]deca-6,9-diene-3,8-dione

Man Yang, Jiawei Hua, Hao Wang, Tao Ma, Chengkou Liu, Wei He, Ning Zhu, Yujing Hu, Zheng Fang, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Nanjing Tech University

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

13 Scopus citations

Abstract

A metal- and oxidant-free route for affording azaspiro[4.5]deca-6,9-diene-3,8-dione via photomediated iodinated spirocyclization of N-(4-methoxybenzyl) propiolamide has been developed. The reaction underwent a radical addition/ipso-cyclization/dearomatization process at room temperature and successfully constructed C-C and C-I bonds. This green and convenient approach could be generally expanded to produce a range of iodinated spirocyclization products in moderate to good yields.

Original language	English
Pages (from-to)	8445-8457
Number of pages	13
Journal	Journal of Organic Chemistry
Volume	87
Issue number	13
DOIs	https://doi.org/10.1021/acs.joc.2c00579
State	Published - 1 Jul 2022

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title = "Photomediated Spirocyclization of N-Benzyl Propiolamide with N-Iodosuccinimide for Access to Azaspiro[4.5]deca-6,9-diene-3,8-dione",

abstract = "A metal- and oxidant-free route for affording azaspiro[4.5]deca-6,9-diene-3,8-dione via photomediated iodinated spirocyclization of N-(4-methoxybenzyl) propiolamide has been developed. The reaction underwent a radical addition/ipso-cyclization/dearomatization process at room temperature and successfully constructed C-C and C-I bonds. This green and convenient approach could be generally expanded to produce a range of iodinated spirocyclization products in moderate to good yields.",

author = "Man Yang and Jiawei Hua and Hao Wang and Tao Ma and Chengkou Liu and Wei He and Ning Zhu and Yujing Hu and Zheng Fang and Kai Guo",

year = "2022",

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doi = "10.1021/acs.joc.2c00579",

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T1 - Photomediated Spirocyclization of N-Benzyl Propiolamide with N-Iodosuccinimide for Access to Azaspiro[4.5]deca-6,9-diene-3,8-dione

AU - Yang, Man

AU - Hua, Jiawei

AU - Wang, Hao

AU - Ma, Tao

AU - Liu, Chengkou

AU - He, Wei

AU - Zhu, Ning

AU - Hu, Yujing

AU - Fang, Zheng

AU - Guo, Kai

PY - 2022/7/1

Y1 - 2022/7/1

N2 - A metal- and oxidant-free route for affording azaspiro[4.5]deca-6,9-diene-3,8-dione via photomediated iodinated spirocyclization of N-(4-methoxybenzyl) propiolamide has been developed. The reaction underwent a radical addition/ipso-cyclization/dearomatization process at room temperature and successfully constructed C-C and C-I bonds. This green and convenient approach could be generally expanded to produce a range of iodinated spirocyclization products in moderate to good yields.

AB - A metal- and oxidant-free route for affording azaspiro[4.5]deca-6,9-diene-3,8-dione via photomediated iodinated spirocyclization of N-(4-methoxybenzyl) propiolamide has been developed. The reaction underwent a radical addition/ipso-cyclization/dearomatization process at room temperature and successfully constructed C-C and C-I bonds. This green and convenient approach could be generally expanded to produce a range of iodinated spirocyclization products in moderate to good yields.

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U2 - 10.1021/acs.joc.2c00579

DO - 10.1021/acs.joc.2c00579

M3 - 文章

AN - SCOPUS:85133518424

SN - 0022-3263

VL - 87

SP - 8445

EP - 8457

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -

Photomediated Spirocyclization of N-Benzyl Propiolamide with N-Iodosuccinimide for Access to Azaspiro[4.5]deca-6,9-diene-3,8-dione

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