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One-pot and divergent synthesis of polysubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/Corey–Chaykovsky epoxidation reactions

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成果类型:
期刊论文
作者:
Yang, Mao-Lin;Pan, Hong-Ling;Kong, Han-Han;Ding, Ming-Wu
通讯作者:
Ding, Ming-Wu(mwding@mail.ccnu.edu.cn)
作者机构:
[Kong, Han-Han; Yang, Mao-Lin; Pan, Hong-Ling; Ding, Ming-Wu] Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构:
[Ming-Wu Ding] K
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University, Wuhan 430079, P. R. China
语种:
英文
关键词:
Epoxidation;Synthesis (chemical);Carboxymethyl;Divergent synthesis;Epoxidation reactions;Isocyanides;Knoevenagel condensation;One-pot synthesis;Condensation
期刊:
Organic Chemistry Frontiers
ISSN:
2052-4110
年:
2022
卷:
9
期:
21
页码:
5983-5988
基金类别:
We gratefully acknowledge the financial support for this work from the National Natural Science Foundation of China (No. 21572075) and the 111 Project B17019.
机构署名:
本校为第一机构
院系归属:
化学学院
摘要:
A new one-pot and divergent synthesis of multisubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/Corey-Chaykovsky epoxidation reactions was developed. The four-component reactions of 2-acylanilines, aldehydes, (carboxymethyl)(dimethyl)sulfonium bromides and isocyanides gave Ugi adducts, which were subsequently treated with DBU to produce polysubstituted quinolin-2(1H)-ones or oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones in good overall yields by intramolecula...

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