Synthesis 2019; 51(15): 2977-2983
DOI: 10.1055/s-0037-1611778
paper
© Georg Thieme Verlag Stuttgart · New York

Direct Synthesis of Vicinal Tricarbonyl Amides by Coupling of α-Oxo Acid Chlorides with Carbamoylsilanes

Yuling Han
a   College of Chemistry and Materials Science, Shanxi Normal University, Linfen 041004, P. R. China
,
Yuping Li
a   College of Chemistry and Materials Science, Shanxi Normal University, Linfen 041004, P. R. China
,
Shenghua Han
b   College of Chemistry and Engineering, Shanxi Datong University, Datong 037009, P. R. China   Email: jjxxcc2002@126.com   Email: chenjx@sxnu.edu.cn
,
Pengpeng Zhang
a   College of Chemistry and Materials Science, Shanxi Normal University, Linfen 041004, P. R. China
,
Jianxin Chen*
a   College of Chemistry and Materials Science, Shanxi Normal University, Linfen 041004, P. R. China
› Author Affiliations
This research was supported by the Shanxi Province Foundation for Returnees (No. 0713), the Natural Science Foundation of Shanxi Province (No. 2012011046-9), and the Foundation of Shanxi Normal University (SD2015CXXM-83), P. R. China.
Further Information

Publication History

Received: 27 January 2019

Accepted after revision: 11 March 2019

Publication Date:
03 April 2019 (online)


Abstract

A convenient synthetic method for vicinal tricarbonyl amides by the cross-coupling reaction of α-oxo acid chlorides with carbamoylsilanes is developed. The reaction tolerates a broad range of substituents on the amido nitrogen of carbamoylsilanes, and directly affords good yields of vicinal tricarbonyl amides under mild conditions without use of oxidants. The reaction of carbamoylsilanes with oxalyl chloride has also been explored, and is accompanied by decarbonylation to give vicinal tricarbonyl amides.

Supporting Information