Journal of Heterocyclic Chemistry p. 1163 - 1172 (1997)
Update date:2022-07-29
Topics:
Bridges, Alexander J.
Zhou, Hairong
Various 2-fluorobenzonitriles were converted to the corresponding 3-amino[1]benzothiophenecarboxylic acid esters, which in turn were annulated with formamidine or various equivalents to produce the desired tricyclic benzothienopyrimidines. Various methoxy and nitro/amino substituants were placed on the phenyl ring, requiring several different strategies to prepare the desired benzothiophenes. Several different pyrimidone annulations were also required. The use of an electron rich 2-bromobenzonitrile in a four-step one-pot low temperature lithiation sequence to produce highly electron-rich amino[1]benzothiophenecarboxylate esters is also described. The synthesis of 7-amino-8-fluoro[1]benzothieno[3,2-d]pyrimid-4(3H)-one was relatively straightforward, but synthesis of the corresponding 7-amino-8-protio analogue proved to be very difficult, and required several approaches before a successful one was found.
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Doi:10.1021/ja01057a032
(1964)Doi:10.1039/CT9211900830
(1921)Doi:10.1016/S0040-4020(97)10066-7
(1997)Doi:10.1039/a706249d
(1997)Doi:10.1021/jm701191z
(2008)Doi:10.1055/s-1997-1009
(1997)