Synlett 2020; 31(07): 703-707
DOI: 10.1055/s-0039-1691583
letter
© Georg Thieme Verlag Stuttgart · New York

Ultrasound-Assisted Synthesis of N-Acylcyanamides and N-Acyl-Substituted Imidazolones from Carboxylic Acids by Using Trichloroisocyanuric Acid/Triphenylphosphine

Wong Phakhodee
a  Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand   Email: Mookdap55@gmail.com
b  Research Center on Chemistry for Development of Health Promoting Products from Northern Resources, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
,
Dolnapa Yamano
a  Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand   Email: Mookdap55@gmail.com
,
Mookda Pattarawarapan
a  Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand   Email: Mookdap55@gmail.com
b  Research Center on Chemistry for Development of Health Promoting Products from Northern Resources, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
› Author Affiliations
This research work was partially supported by Chiang Mai University. Financial support from The Thailand Research Fund through the Royal Golden Jubilee Ph.D. Program to D.Y. (Grant No. PHD/0023/2559) and the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education Commission, Ministry of Education, Thailand are also gratefully acknowledged.
Further Information

Publication History

Received: 11 December 2019

Accepted after revision: 07 January 2020

Publication Date:
28 January 2020 (online)


Abstract

A convenient ultrasound-assisted one-pot synthesis of N-acylcyanamides starting from readily available carboxylic acids and sodium cyanamide has been developed. Upon activation in the presence of trichloroisocyanuric acid (TCCA) and triphenylphosphine, a range of carboxylic acids was converted into N-acylcyanamides in good to excellent yields within 10 minutes at room temperature without base. Remarkably, N-acyl-substituted imidazolones were readily accessible through guanylation-cyclization of the in situ generated N-acylcyanamides.

Supporting Information

 
  • References and Notes

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