5265-19-0Relevant articles and documents
Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions
Bai, Jin,Yan, Sijia,Zhang, Zhuxia,Guo, Zhen,Zhou, Cong-Ying
supporting information, p. 4843 - 4848 (2021/06/28)
A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.
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.
Palladium-catalyzed C-H cyclization in water: A milder route to 2-arylbenzothiazoles
Inamoto, Kiyofumi,Nozawa, Kanako,Kondo, Yoshinori
supporting information; experimental part, p. 1678 - 1682 (2012/07/17)
Water was successfully employed as a reaction medium in palladium-catalyzed C-H cyclization of thiobenzanilides. Reactions efficiently proceeded under considerably mild conditions such as 40 °C in water, providing a more practical, greener method for the synthesis of 2-arylbenzothiazoles. For some substrates, the addition of an amphiphilic surfactant greatly enhanced the process. The method represents a rare example of palladium-catalyzed C-H functionalization processes performed in water. Georg Thieme Verlag Stuttgart · New York.
Palladium-catalyzed synthesis of 2-substituted benzothiazoles via a C-H functionalization/intramolecular C-S bond formation process
Inamoto, Kiyofumi,Hasegawa, Chisa,Hiroya, Kou,Doi, Takayuki
supporting information; experimental part, p. 5147 - 5150 (2009/05/30)
(Chemical Equation Presented) Catalytic synthesis of 2-substituted benzothiazoles from thiobenzanilides was achieved in the presence of a palladium catalyst through C-H functionalization/C-S bond formation. This method features the use of a novel catalytic system consisting of 10 mol % of Pd(II), 50 mol % of Cu(I), and 2 equiv of Bu4NBr that produced variously substituted benzothiazoles in high yields with good functional group tolerance.
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.
Efficient synthesis of thiobenzanilides by Willgerodt-Kindler reaction with base catalysts
Okamoto, Ken,Yamamoto, Takakazu,Kanbara, Takaki
, p. 2687 - 2690 (2008/02/11)
Willgerodt-Kindler reaction between anilines and benzaldehydes readily proceeded in the presence of catalytic amount of Na2S·9H 2O to give thiobenzanilides in moderate to good yields. The base catalyst was also available for preparation of primary thiobenzamide. Georg Thieme Verlag Stuttgart.
Attempted synthesis of 2-azetidinones via ester enolate condensation reactions with imines and thioimidates
Sharma,Saluja, Aarti,Bhaduri, Susmita,Kanwar, Seema
, p. 1964 - 1969 (2007/10/03)
Reaction of the imines 1 and ethyl isobutyrate in the presence of LDA yields β-lactams 2, whereas thioimidate 4 with the same enolate gives the substituted products 5. When phosphorous containing heterocyclic compound 9 is treated with the enolate of ethyl isobutyrate, a mixture of substituted products 10 and 11 is produced. Mechanistic details of these reactions are described.
