Synthesis of Benzoindolizines through 1,5-Electrocyclization/Oxidation Cascades

Si-Wei Liu; Ying-Juan Gao; Yin Shi; Lin Zhou; Xue Tang; Hai-Lei Cui

doi:10.1021/acs.joc.8b02065

Synthesis of Benzoindolizines through 1,5-Electrocyclization/Oxidation Cascades

J Org Chem. 2018 Nov 16;83(22):13754-13764. doi: 10.1021/acs.joc.8b02065. Epub 2018 Nov 5.

Authors

Si-Wei Liu¹, Ying-Juan Gao¹, Yin Shi¹, Lin Zhou¹, Xue Tang^{1

2}, Hai-Lei Cui¹

Affiliations

¹ Laboratory of Asymmetric Synthesis , Chongqing University of Arts and Sciences , 319 Honghe Avenue , Yongchuan, Chongqing , 402160 , China.
² State Key Laboratory Breeding Base of Systematic Research, Development and Utilization of Chinese Medicine Resources, School of Pharmacy , Chengdu University of Traditional Chinese Medicine , Chengdu 611137 , China.

PMID: 30372066
DOI: 10.1021/acs.joc.8b02065

Abstract

This study presents a convenient synthesis of pyrrolo[1,2- a]quinolines and pyrrolo[2,1- a]isoquinolines with simple quinolines or isoquinolines and Morita-Baylis-Hillman carbonates in the presence of copper acetate. A range of functionalized benzoindolizines could be assembled through an S_N2'/deprotonation/1,5-electrocyclization/oxidation cascade pathway in a one-step process.

Publication types

Research Support, Non-U.S. Gov't