Jump to main content
Jump to site search

Issue 18, 2019
Previous Article Next Article

New insight into the chemistry of selenoureas: synthesis and single crystal structural study of diverse derivatives

Author affiliations

Abstract

Reacting benzoyl chloride with KSeCN in acetone at room temperature, followed by treatment in situ with 4-bromoaniline led to N-((4-bromophenyl)carbamoselenoyl)benzamide in 93% yield. The same reaction was observed for 4-methoxybenzoyl chloride and 4-pentafluorosulfanylaniline, leading to N-((4-pentafluorosulfanylphenyl)carbamoselenoyl)-4-methoxybenzamide in 76% yield. Interestingly, under the same conditions, 4-methoxybenzoyl chloride and 4-bromoaniline gave rise of the unexpected 2-((4-bromophenyl)amino)-2-methylpropanenitrile and 6-bromo-2,2,4-trimethyl-1,2-dihydroquinoline in 45% and 52% yields. Further, the equivalent reaction of 4-nitrobenzoyl chloride and 4-pentafluorosulfanylaniline afforded an additional 3-(4-nitrobenzoyl)imino-5-(4-(pentafluorosulfanyl)phenylamino)-1,2,4-diselenazole in 19% yield apart from the expected 4-nitro-N-((4-(pentafluorosulfanyl)phenyl)carbamoselenoyl)benzamide in 79% yield. Furthermore, a series of five-membered selenium heterocycles was obtained from the reaction of N-acylselenoureas with various phenacyl bromides. All new compounds were characterised spectroscopically, and twelve X-ray single crystal structures were also discussed.

Graphical abstract: New insight into the chemistry of selenoureas: synthesis and single crystal structural study of diverse derivatives

Back to tab navigation

Supplementary files

Article information


Submitted
27 Feb 2019
Accepted
08 Apr 2019
First published
17 Apr 2019

New J. Chem., 2019,43, 7035-7043
Article type
Paper

New insight into the chemistry of selenoureas: synthesis and single crystal structural study of diverse derivatives

G. Hua, J. Du, C. L. Carpenter-Warren, D. B. Cordes, A. M. Z. Slawin and J. D. Woollins, New J. Chem., 2019, 43, 7035
DOI: 10.1039/C9NJ01059A

Social activity

Search articles by author

Spotlight

Advertisements