期刊
TETRAHEDRON
卷 73, 期 5, 页码 481-493出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.12.024
关键词
Nucleophilic addition; Nitrogen heterocycles; Regioselectivity; Organomagnesium compounds; Organolithium compounds
资金
- National Science Center [N N204 219640]
- Faculty of Chemical Technology and Engineering, West Pomeranian University of Technology, Szczecin
Novel benzylation reagents BnR2MgLi were obtained by mixing benzylmagnesium chloride (BnMgCl) and appropriate organolithium compounds (RLi). As BnR2MgLi complexes are more nucleophilic than the parent Grignard compound they enabled regioselective C6-addition to electrophilic N-substituted 2(thio)-pyridones and C4-addition to poorly reactive NH 2-(thio)pyridones in high and good yields, respectively. Thus, the application of these new reagents in efficient synthesis of 6-benzy1-3,6-dihydroand 4-benzy1-3,4-dihydropyridin-2(1H)-ones is described. The prospect of wider application of BnR2MgLi in 1,4-addition to other electrophiles, comprising six-membered alpha,beta-unsaturated systems is also presented. (C) 2016 Elsevier Ltd. All rights reserved.
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