Journal of Organic Chemistry p. 5814 - 5819 (1995)
Update date:2022-08-03
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Karp, Gary M.
A series of 7-, 8-, and 9-bromo- and iodo-1,4-benzodiazepine-2,5-diones have been prepared and examined as substrates for palladium(II)-mediated coupling reactions with alkenes, alkynes, arylstannanes, and heteroarylstannanes.The benzodiazepinediones 6a,e,g were prepared from the reaction of o-nitrobenzoyl chlorides 3a-c and methyl tert-butylglycinate followed by nitro reduction and cyclization.Regioselective halogenation gave 6c,d,f.Bromo- and iodobenzodiazepinediones 6c,d,f,g were then converted to alkenyl-, alkynyl-, aryl-, and heteroaryl-substituted benzodiazepinediones in moderate to good yield in the presence of palladium(II).
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Doi:10.1016/0040-4020(95)00657-T
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