Nucleophilic substitution approach towards 1,3-dimethylbarbituric acid derivatives: new synthetic routes and crystal structures

Content Provider	Semantic Scholar
Author	Mallah, Eyad Sweidan, Kamal Engelmann, Joern Steimann, Manfred Kuhn, Norbert Maier, Martin E.
Copyright Year	2012
Abstract	We describe simple, convenient and high-yielding nucleophilic substitution reactions to synthesize new derivatives of 1,3-dimethylbarbituric acid ( 1a ). Based on its active C5 position, condensing 1a with sulfuryl chloride gives the corresponding 5,5-dichloro-1,3-dimethylbarbituric acid ( 13 ). The latter was reacted with silver nitrite and potassium cyanide to afford 5-chloro-5-nitro-1,3-dimethylbarbituric acid ( 14 ) and 5-cyano-1,3-dimethylbarbiturate ( 17 ), respectively. Furthermore, by employing the nucleophilic character of 2,3-dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene ( 8 ) the obtained compounds 13 and 14 have been converted to 2-chloro-1,3-diisopropyl-4,5-dimethyl-1 H -imidazol-3-ium-1,3-dimethyl-5-nitro-1,3-dimethylbarbiturate ( 18 ) and 1,3-dimethylbarbituric acid trimer ( 21 ), respectively. X-ray structures for compounds 13 , 14 , 17 , 18 and 21 were determined.
Starting Page	1005
Ending Page	1010
Page Count	6
File Format	PDF HTM / HTML
DOI	10.1016/j.tet.2011.11.093
Alternate Webpage(s)	https://www.uop.edu.jo/download/research/members/349_2160_Eyad.pdf
Alternate Webpage(s)	https://doi.org/10.1016/j.tet.2011.11.093
Volume Number	68
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article