450375-86-7Relevant academic research and scientific papers
Decomposition of benzoylthioureas into benzamides and thiobenzamides under solvent-free conditions using iodine-alumina as the catalyst and its mechanistic study by density functional theory
Nahakpam, Lokendrajit,Chipem, Francis A. S.,Chingakham, Brajakishor S.,Laitonjam, Warjeet S.
supporting information, p. 2240 - 2247 (2015/03/18)
The breaking down of benzoylthioureas to benzamides and thiobenzamides in a single route using iodine-alumina as the catalyst under solvent-free conditions is highlighted. Results show that when an electron donating group, such as the methyl or methoxy group, is at the para-position of the aryl group of 1, benzamide (2) is the favoured product. When an electron withdrawing group, such as the chlorine or nitro group, is at the para-position of the aryl group of 1, thiobenzamide (3) is the favoured product. From the study of the reaction mechanism, it may be postulated that the formation of benzamide is due to the migration of the aryl group, whereas the formation of thiobenzamide may be due to the migration of the phenyl group. Thus, a new method for the formation of benzamides and thiobenzamides was developed.
Organocatalytic syntheses of benzoxazoles and benzothiazoles using aryl iodide and oxone via C-H functionalization and C-O/S bond formation
Alla, Santhosh Kumar,Sadhu, Pradeep,Punniyamurthy, Tharmalingam
, p. 7502 - 7511 (2014/09/16)
An organocatalytic protocol for the syntheses of 2-substituted benzoxazoles and benzothiazoles is described from alkyl-/arylanilides and alkyl-/arylthioanilides using 1-iodo-4-nitrobenzene as catalyst and oxone as an inexpensive and environmentally safe terminal oxidant at room temperature in air via oxidative C-H functionalization and C-O/S bond formation. The procedure is simple and general and provides an effective route for the construction of functionalized 2-alkyl-/arylbenzoxazoles and 2-alkyl-/arylbenzothiazoles with moderate to high yields. The synthetic and mechanistic aspects have been 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.
