95479-51-9Relevant academic research and scientific papers
Synthesis and Stereochemistry of Reissert Compounds from Benzothiazole
Pandya, Ashish,Gibson, Harry W.
, p. 2851 - 2855 (2007/10/02)
Benzothiazole Reissert compounds 1-5 were synthesized, characterized and alkylated to produce 6-9.Conformational analysis of 2 by the use of high resolution (400 Hz) variable temperature NMR spectroscopy indicated that the Z to E amide conformer ratio is 79:21 (+/- 3 percent) in CDCl3 at 213 K (-60 deg C) and 57:43 (+/- 3 percent) in C6D5CD3 at 213 K.Aromatic solvent induced shifts were employed to determine the distribution of rotamers and indicated that the alkylated benzothiazole Reissert compound 8 existed in only the Z amide conformation.Hindered aryl-carbonyl rotation was also detected in the Reissert compounds.
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.
Reissert Compound Formation with Five-membered Ring Heterocycles using Trimethylsilyl Cyanide
Uff, Barrie C.,Chen, S. L. Anne A.,Ho, Yee-Ping,Popp, Frank D.,Kant, Joydeep
, p. 1245 - 1246 (2007/10/02)
Treatment of benzothiazole with trimethylsilyl cyanide and an acid chloride in CH2Cl2 gives the N-acyl-2-cyano-2,3-dihydrobenzothiazole in good yield; benzoxazole similarly is converted into a five-membered ring Reissert compound, providing the first exam
