New insight into the chemistry of selenoureas : synthesis and single crystal structural study of diverse derivatives
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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.
Hua , G , Du , J , Carpenter-Warren , C L , Cordes , D B , Slawin , A M Z & Woollins , J D 2019 , ' New insight into the chemistry of selenoureas : synthesis and single crystal structural study of diverse derivatives ' , New Journal of Chemistry , vol. 43 , no. 18 , pp. 7035-7043 .
New Journal of Chemistry
Copyright © 2019 The Author(s). This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1039/C9NJ01059A
DescriptionAuthors are grateful to the University of St Andrews for financial support and the EPSRC National Mass Spectrometry Service Centre (Swansea) for mass spectral measurements.
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