221541-73-7Relevant academic research and scientific papers
Synthesis, and structure verification of an analogue of kuanoniamine A
Lyon, Michael A.,Lawrence, Simon,Williams, David J.,Jackson, Yvette A.
, p. 437 - 442 (1999)
Synthesis of 9-phenyl-7H-benzothiazolo[4,5,6-y][2,7]naphthyridin-7-one 11, an analogue of kuanoniamine A 8, is described. The synthesis involves a hetero Diels-Alder reaction of crotonaldehyde dimethylhydrazone with 4,7-dioxo-2-phenylbenzothiazole 18a or with 6-bromo-4,7-dioxo-2-phenylbenzothiazole 18b followed by annelation of the appropriate adduct. Reaction with 18a produced two sets of regioisomers-the thiazoloquinolinediones 19a,b, and the dimethylamino dioxobenzothiazoles 23a,b. The structure of 23b was determined by single-crystal X-ray structure analysis. Verification of the other structures, and methods used to improve the Diels-Alder reaction are described.
Conversion of thiobenzamides to benzothiazoles via intramolecular cyclization of the aryl radical cation
Downer-Riley, Nadale K.,Jackson, Yvette A.
, p. 7741 - 7744 (2008/12/20)
A new and general method has been developed for the intramolecular cyclization of thiobenzamides to benzothiazoles via aryl radical cations as reactive intermediates. The method utilizes phenyliodine(III) bis(trifluoroacetate) (PIFA) in trifluoroethanol or cerium ammonium nitrate (CAN) in aqueous acetonitrile at room temperature to effect cyclization within 30 min in moderate yields.
