74821-71-9Relevant academic research and scientific papers
DMSO-mediated palladium-catalyzed cyclization of two isothiocyanates: Via C-H sulfurization: A new route to 2-aminobenzothiazoles
Yao, Guangkai,Wang, Bing-Feng,Yang, Shuai,Zhang, Zhi-Xiang,Xu, Han-Hong,Tang, Ri-Yuan
, p. 3403 - 3406 (2019/02/10)
DMSO was found to activate arylisothiocyanates for self-nucleophilic addition. A subsequent intramolecular C-H sulfurization catalyzed by PdBr2 enables access to a wide range of 2-aminobenzothiazole derivatives in moderate to good yields. This is the first example of a DMSO-mediated Pd-catalyzed synthesis of 2-aminobenzothiazoles through cyclization/C-H sulfurization of two isothiocyanates.
Metal-Free Synthesis of 2-Aminobenzothiazoles via Iodine-Catalyzed and Oxygen-Promoted Cascade Reactions of Isothiocyanatobenzenes with Amines
Xu, Yuanshuang,Li, Bin,Zhang, Xinying,Fan, Xuesen
, p. 9637 - 9646 (2017/09/23)
In this paper, a highly efficient and sustainable synthesis of 2-aminobenzothiazoles through the cascade reactions of isothiocyanatobenzenes with primary or secondary amines by using iodine as a catalyst and oxygen as an oxidant is presented. Mechanistically, the formation of the title compounds involves the in situ formation of the required benzothiourea intermediate followed by its intramolecular cross dehydrogenative coupling of a C(sp2)-H bond and a S-H bond. To our knowledge, this should be the first example in which 2-aminobenzothiazoles are efficiently prepared from simple and cheap isothiocyanates and amines under metal-free conditions by using iodine as a catalyst and molecular oxygen as an oxidant with water as the byproduct. Compared with literature protocols, this method eliminates the use of ortho-halo-substituted precursors, expensive transition-metal catalysts, and hazardous oxidants.
A metal-free synthesis of 2-aminobenzothiazoles through aminyl radical addition to aryl isothiocyanates
He, Yimiao,Li, Jing,Luo, Shuang,Huang, Jinbo,Zhu, Qiang
supporting information, p. 8444 - 8447 (2016/07/07)
A convenient synthesis of 2-aminobenzothiazoles, starting from aryl isothiocyanates and formamides under metal-free conditions, is described. Various secondary and tertiary amine- and even α-amino acid-derived formamides can be used as amino sources in this process. Mechanistic studies suggest that the reaction is initiated by decarbonylative aminyl radical formation in the presence of n-Bu4NI and TBHP, followed by aminyl radical addition to isothiocyanates and cyclization via sulfur centred radical intermediates.
Polymer-supported tribromide as a new solid phase and recyclable catalyst for the synthesis of 2-(n-arylamino)benzothiazoles under solvent-free microwave irradiation conditions
Nahakpam, Lokendrajit,Chingakham, Brajakishor S.,Laitonjam, Warjeet S.
, p. 267 - 272 (2015/01/30)
The solid-phase synthesis of 2-(N-arylamino)benzothiazoles is achieved by reacting substituted thioureas with polymer-supported tribromide. A series of 2-(N-aryl)aminobenzothiazoles is prepared in high yields under microwave irradiation. The method has se
ETUDE DE LA FRAGMENTATION PAR IMPACT ELECTRONIQUE DE DERIVES DU BENZOTHIAZOLE
Claude, Saturnin,Tabacchi, Raffaele,Duc, Laurent,Fuchs, Rudolf,Boosen, Karl-Josef
, p. 682 - 692 (2007/10/02)
The mass spectra of eighteen substituted benzothiazoles are reported and discussed.All these compounds are thermodynamically stable and give an intense molecular ion, which undergoes different types of fragmentation depending on the nature of the substituent which is rarely eliminated directly. β-Cleavage with respect to the heterocyclic double bond is often obseved.Specific 2H-, 13C-, 15N- and 34S-labelling have been used in order to confirm the fragmentation patterns.
