Practical synthesis of N-substituted cyanamides via Tiemann rearrangement of amidoximes

Chia-Chi Lin; Tsung-Han Hsieh; Pen-Yuan Liao; Zhen-Yuan Liao; Chih-Wei Chang; Yu-Chiao Shih; Wen-Hsiung Yeh; Tun-Cheng Chien

doi:10.1021/ol403645y

Practical synthesis of N-substituted cyanamides via Tiemann rearrangement of amidoximes

Org Lett. 2014 Feb 7;16(3):892-5. doi: 10.1021/ol403645y. Epub 2014 Jan 14.

Authors

Chia-Chi Lin¹, Tsung-Han Hsieh, Pen-Yuan Liao, Zhen-Yuan Liao, Chih-Wei Chang, Yu-Chiao Shih, Wen-Hsiung Yeh, Tun-Cheng Chien

Affiliation

¹ Department of Chemistry, National Taiwan Normal University , Taipei 11677, Taiwan.

PMID: 24423009
DOI: 10.1021/ol403645y

Abstract

A facile and general synthesis of various N-substituted cyanamides was accomplished by the Tiemann rearrangement of amidoximes with benzenesulfonyl chlorides (TsCl or o-NsCl) and DIPEA.