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Synthesis 2018; 50(20): 4055-4062
DOI: 10.1055/s-0037-1609548
paper
© Georg Thieme Verlag Stuttgart · New York

Cs2CO3-Promoted C-3 Alkylation of 4-[(2,2-Difluoroethyl)amino]-5,5-disubstituted Furan-2(5H)-ones with Heteroarylmethyl Chlorides

Zhao Yu
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China   Email: wangma@cau.edu.cn
,
Liu Xinlei
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China   Email: wangma@cau.edu.cn
,
Wang Weiwei
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China   Email: wangma@cau.edu.cn
,
Geng Rui
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China   Email: wangma@cau.edu.cn
,
Mingan Wang*
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China   Email: wangma@cau.edu.cn
› Author AffiliationsThis work was financially supported by the National Natural Science Foundation of China (No. 21772229).
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Publication History

Received: 02 April 2018

Accepted after revision: 06 June 2018

Publication Date:
16 July 2018 (online)

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Abstract

4-(2,2-Difluoroethylamino)-3-(heteroarylmethyl)-5,5-disubstituted furan-2(5H)-ones were regioselectively synthesized via C-3 alkylation of 4-(2,2-difluoroethylamino)-5,5-disubstituted furan-2(5H)-ones with heteroarylmethyl chlorides using Cs2CO3 as a base in 62–85% yields. Their structures were characterized by 1H and 13C NMR, HRMS (ESI), and X-ray diffraction. This C-alkylation selectivity was rationalized by bulky hindrance and electron-withdrawing effects.

Key words

5-spirocyclic furan-2(5H)-one - synthesis - regioselectivity - C-alkylation

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    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609548.
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