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

Guoxiong Hua, Junyi Du, Cameron Lewis Carpenter-Warren, David B. Cordes, Alexandra M. Z. Slawin, John D. Woollins

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)7035-7043
Number of pages9
JournalNew Journal of Chemistry
Volume43
Issue number18
Early online date17 Apr 2019
Publication statusPublished - 14 May 2019

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