127245-91-4Relevant academic research and scientific papers
Reissert Compound Formation with Fused Five-Membered Ring Heterocycles
Uff, Barrie C.,Ho, Yee-Ping,Brown, David S.,Fisher, Ian,Popp, Frank D.,Kant, Joydeep
, p. 2652 - 2681 (2007/10/02)
Reissert compounds have been prepared in high yield from benzothiazole by use of trimethylsilyl cyanide as source of cyanide in a single phase system.Analogues have been made from benzoxazole, indazole and 1-methylindazole but the method was unsuccessful with 1,2-benzisoxazole and pyrazole.Conjugate base alkylation followed by removal of the Reissert grouping provides a route to 2-alkylbenzothiazoles and -benzoxazoles, and 3-alkylated indazoles.Efficient access to pyridobenzothiazole and benzothiazoloisoquinoline derivatives results from appropriate intramolecular cyclisations.A crystal structure determination of 3-benzoyl-2,3-dihydro-2-benzothiazolecarbonitrile is reported.
