Synthesis 2020; 52(03): 459-470
DOI: 10.1055/s-0039-1690229
paper
© Georg Thieme Verlag Stuttgart · New York

Iodine-Mediated Oxidative Cyclization of 2-(Pyridin-2-yl)acetate Derivatives with Alkynes: Condition-Controlled Selective Synthesis of Multisubstituted Indolizines

Lisheng He
a  State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 3491 Baijin Road, Guiyang 550014, P. R. of China
b  The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, 3491 Baijin Road, Guiyang 550014, P. R. of China
c  College of Pharmacy, Guizhou Medical University, 9 Beijing Road, Guiyang, Guizhou 550004, P. R. of China   Email: yangyuzhu15@126.com   Email: wdpan@163.com
,
Yuzhu Yang
a  State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 3491 Baijin Road, Guiyang 550014, P. R. of China
b  The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, 3491 Baijin Road, Guiyang 550014, P. R. of China
c  College of Pharmacy, Guizhou Medical University, 9 Beijing Road, Guiyang, Guizhou 550004, P. R. of China   Email: yangyuzhu15@126.com   Email: wdpan@163.com
,
Xiaolan Liu
a  State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 3491 Baijin Road, Guiyang 550014, P. R. of China
b  The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, 3491 Baijin Road, Guiyang 550014, P. R. of China
c  College of Pharmacy, Guizhou Medical University, 9 Beijing Road, Guiyang, Guizhou 550004, P. R. of China   Email: yangyuzhu15@126.com   Email: wdpan@163.com
,
Guangyan Liang
a  State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 3491 Baijin Road, Guiyang 550014, P. R. of China
b  The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, 3491 Baijin Road, Guiyang 550014, P. R. of China
c  College of Pharmacy, Guizhou Medical University, 9 Beijing Road, Guiyang, Guizhou 550004, P. R. of China   Email: yangyuzhu15@126.com   Email: wdpan@163.com
,
Chunyan Li
a  State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 3491 Baijin Road, Guiyang 550014, P. R. of China
b  The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, 3491 Baijin Road, Guiyang 550014, P. R. of China
c  College of Pharmacy, Guizhou Medical University, 9 Beijing Road, Guiyang, Guizhou 550004, P. R. of China   Email: yangyuzhu15@126.com   Email: wdpan@163.com
,
Daoping Wang
a  State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 3491 Baijin Road, Guiyang 550014, P. R. of China
b  The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, 3491 Baijin Road, Guiyang 550014, P. R. of China
c  College of Pharmacy, Guizhou Medical University, 9 Beijing Road, Guiyang, Guizhou 550004, P. R. of China   Email: yangyuzhu15@126.com   Email: wdpan@163.com
,
Weidong Pan
a  State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 3491 Baijin Road, Guiyang 550014, P. R. of China
b  The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, 3491 Baijin Road, Guiyang 550014, P. R. of China
c  College of Pharmacy, Guizhou Medical University, 9 Beijing Road, Guiyang, Guizhou 550004, P. R. of China   Email: yangyuzhu15@126.com   Email: wdpan@163.com
› Author Affiliations
Financial supports from the Natural Science Foundation of Guizhou Province of China (QKHJC[2017]1117, QKHJC[2018]1109, QKHPTRC[2017]5718), and West Light Foundation of The Chinese Academy of Sciences are acknowledged.
Further Information

Publication History

Received: 20.08.20109

Accepted after revision: 07 October 2019

Publication Date:
29 October 2019 (online)

Abstract

An iodine-mediated oxidative cyclization reaction between 2-(pyridin-2-yl)acetate derivatives and different alkynes has been developed, which provides regioselective and chemoselective syntheses of multiply substituted indolizines under modified reaction conditions. Plausible mechanisms have been proposed to explain the selective syntheses of indolizines. This protocol can be also applied to the stepwise synthesis of 2,2′-biindolizines.

Supporting Information

 
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