Synthesis 2020; 52(03): 378-392
DOI: 10.1055/s-0039-1690036
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© Georg Thieme Verlag Stuttgart · New York

Diverse One-Pot Electrophilic Trapping Reactions of 2-Quinolyl­zincates with Acyl Chlorides and Allyl Iodide

Hye Jin Jeong
a  Department of Chemistry, Seoul Women’s University, Seoul 01797, South Korea   Email: sknam@swu.ac.kr
,
Suyeon Chae
a  Department of Chemistry, Seoul Women’s University, Seoul 01797, South Korea   Email: sknam@swu.ac.kr
,
Keunhong Jeong
b  Department of Chemistry, Korea Military Academy, Seoul 01805, South Korea, Email: doas1mind@gmail.com
,
a  Department of Chemistry, Seoul Women’s University, Seoul 01797, South Korea   Email: sknam@swu.ac.kr
› Author Affiliations
This work was supported by a research grant from Seoul Women’s University (2019).
Further Information

Publication History

Received: 02 September 2019

Accepted after revision: 09 November 2019

Publication Date:
21 November 2019 (online)

Abstract

The tandem acylation reactions of 2-quinolylzincates under one-pot reaction conditions facilitated the formation of biologically active (Z)-3-alkylidenephthalides and multifunctionalized quinoline derivatives at specific positions. The reactions of these zincates with allyl iodide produced three different types of temperature- and alkyl-ligand-dependent C-2 homologated quinolines. The reaction mechanisms for the formation of the presented products from 2-quinolylzincates are also proposed in detail.

Supporting Information

 
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