Transamidation for the Synthesis of Primary Amides at Room Temperature

Jiajia Chen; Yuanzhi Xia; Sunwoo Lee

doi:10.1021/acs.orglett.0c00958

Transamidation for the Synthesis of Primary Amides at Room Temperature

Org Lett. 2020 May 1;22(9):3504-3508. doi: 10.1021/acs.orglett.0c00958. Epub 2020 Apr 16.

Authors

Jiajia Chen^{1

2}, Yuanzhi Xia², Sunwoo Lee¹

Affiliations

¹ Department of Chemistry, Chonnam National University, Gwangju, 61186, Republic of Korea.
² College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. China.

PMID: 32298591
DOI: 10.1021/acs.orglett.0c00958

Abstract

Various primary amides have been synthesized using the transamidation of various tertiary amides under metal-free and mild reaction conditions. When (NH₄)₂CO₃ reacts with a tertiary amide bearing an N-electron-withdrawing substituent, such as sulfonyl and diacyl, in DMSO at 25 °C, the desired primary amide product is formed in good yield with good funcctional group tolerance. In addition, N-tosylated lactam derivatives afforded their corresponding N-tosylamido alkyl amide products via a ring opening reaction.