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Synthesis 2017; 49(19): 4517-4522
DOI: 10.1055/s-0036-1588498
paper
© Georg Thieme Verlag Stuttgart · New York

Convenient Synthesis of Oxazolo[5,4-h]pyrrolo[4,3,2-de]quino­lones via Hypervalent Iodine Mediated Intramolecular Oxidative Cyclization

Chun-Meng Wang
Jiangsu Key Laboratory of Drug Design & Optimization, Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, P. R. of China   Email: chslp@cpu.edu.cn
,
Sheng-Wei Yang
Jiangsu Key Laboratory of Drug Design & Optimization, Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, P. R. of China   Email: chslp@cpu.edu.cn
,
Kai-Xiang Tang
Jiangsu Key Laboratory of Drug Design & Optimization, Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, P. R. of China   Email: chslp@cpu.edu.cn
,
Tian-Hong Gao
Jiangsu Key Laboratory of Drug Design & Optimization, Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, P. R. of China   Email: chslp@cpu.edu.cn
,
Bo Pang
Jiangsu Key Laboratory of Drug Design & Optimization, Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, P. R. of China   Email: chslp@cpu.edu.cn
,
Yu-Ting Chen
Jiangsu Key Laboratory of Drug Design & Optimization, Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, P. R. of China   Email: chslp@cpu.edu.cn
,
Jing Wu
Jiangsu Key Laboratory of Drug Design & Optimization, Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, P. R. of China   Email: chslp@cpu.edu.cn
,
Jia Liu
Jiangsu Key Laboratory of Drug Design & Optimization, Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, P. R. of China   Email: chslp@cpu.edu.cn
,
Yu-Fan Shi
Jiangsu Key Laboratory of Drug Design & Optimization, Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, P. R. of China   Email: chslp@cpu.edu.cn
,
Li-Ping Sun*
Jiangsu Key Laboratory of Drug Design & Optimization, Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, P. R. of China   Email: chslp@cpu.edu.cn
› Author AffiliationsWe are grateful for the funds supported by the National Natural Science Foundation (No. 21472243), the Qing Lan Project in Jiangsu Province, and the National College Students Innovation Training Program.
Further Information

Publication History

Received: 20 March 2017

Accepted after revision: 16 June 2017

Publication Date:
19 July 2017 (online)

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Abstract

A convenient and practical method has been developed for the synthesis of substituted oxazolo[5,4-h]pyrrolo[4,3,2-de]quinolones via the intramolecular oxidative cyclization by using PIFA as oxidant and TMSOTf as additive in DCE under an air atmosphere. The reaction proceeds in good yields and has good functional groups tolerance.

Key words

intramolecular - PIFA - oxidative cyclization - C–O formation - pyrrolo[4,3,2-de]quinolone

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588498.
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