20614-71-5Relevant academic research and scientific papers
KOtBu-Promoted Halogen-Bond-Assisted Intramolecular C-S Cross-Coupling of o-Iodothioanilides for the Synthesis of 2-Substituted Benzothiazoles
Nandy, Anuradha,Sekar, Govindasamy
, p. 15825 - 15834 (2021/11/01)
An efficacious and mild KOtBu-promoted intramolecular C-S cross-coupling of ortho-iodothioanilides in conjunction with a catalytic quantity of phenanthroline as an additive has been described for the convenient synthesis of 2-substituted benzothiazoles. The methodology is suitable for attaining a wide variety of 2-alkyl- and 2-aryl-substituted benzothiazoles. Single-crystal XRD, DFT calculations, NMR, and UV studies suggest that halogen bonds between the units of ortho-iodothioanilides may assist in the electron transfer process.
Iodine-promoted ring-opening methylation of benzothiazoles with dimethyl sulfite
Guo, Ying-Qiong,Chen, Fan,Deng, Chen-Liang,Zhang, Xing-Guo
supporting information, p. 1923 - 1926 (2021/03/02)
A halogen-bond promoted ring-opening methylation of benzothiazoles has been developed using dimethyl sulphite as a methylating reagent in the presence of a base. This approach represents a simple and efficient synthesis ofN-methyl-N-(o-methylthio)phenyl amides, and features direct construction of both N-Me and S-Me bonds in a one-pot reaction through the decomposition of easily prepared benzothiazoles.
Nickel(ii)-catalyzed addition of aryl-, alkenyl-, and alkylboronic acids to alkenylazaarenes
Liu, Xing-Yu,Tan, Yun-Xuan,Wang, Xin,Xu, Hao,Wang, Yu-Hui,Tian, Ping,Lin, Guo-Qiang
supporting information, p. 4038 - 4042 (2020/05/18)
A nickel(II)-catalyzed addition of aryl-, alkenyl-, and alkylboronic acids to alkenylazaarenes was presented. This reaction exhibited high efficiency (up to 93% yield), a broad substrate scope (seven types of heterocycles), and good functional group compatibility. The resulting products can be further transformed to many useful building blocks. Finally, the preliminary studies suggested that the adjacent N atom of the heterocycles was essential for the high reactivity.
An efficient synthesis of benzothiazole using tetrabromomethane as a halogen bond donor catalyst
Kazi, Imran,Sekar, Govindasamy
, p. 9743 - 9756 (2019/12/02)
An efficient and mild protocol has been developed for the synthesis of 2-substituted benzothiazole under solvent- and metal-free conditions using CBr4 as the catalyst. This process involves the activation of a thioamide through halogen bond formation between the sulphur atom of the thioamide and bromine atom of the CBr4 molecule. The presence of halogen-bonding interaction between N-methylthioamides and tetrabromomethane has been demonstrated with several control experiments, spectroscopic analysis and density functional theory (DFT). This methodology has a wide substrate scope for the synthesis of both 2-alkyl and 2-aryl substituted benzothiazoles.
Iron-catalyzed C-H alkylation of heterocyclic C-H bonds
Babu, Kaki Raveendra,Zhu, Nengbo,Bao, Hongli
, p. 46 - 49 (2017/11/28)
An efficient, iron-catalyzed C-H alkylation of benzothiazoles by using alkyl diacyl peroxides and alkyl tertbutyl peresters which are readily accessible from carboxylic acids to synthesize 2-alkylbenzothiazoles is developed. This reaction is environmentally benign and compatible with a broad range of functional groups. Various primary, secondary, and tertiary alkyl groups can be efficiently incorporated into diverse benzothiazoles. The effectiveness of this method is illustrated by late-stage functionalization of biologically active heterocycles.
Method for catalytic synthesis of 2-substituted benzothiazole compound by utilizing Yb/MCM-41 molecular sieve-based catalyst
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Paragraph 0125; 0126; 0127; 0128; 0129, (2016/10/17)
The invention relates to a method for the catalytic synthesis of a 2-substituted benzothiazole compound by utilizing a Yb/MCM-41 molecular sieve-based catalyst. The method comprises the steps of (a) subjecting 2-amino thiophenol, an aldehyde compound and
Acceptorless dehydrogenative synthesis of benzothiazoles and benzimidazoles from alcohols or aldehydes by heterogeneous Pt catalysts under neutral conditions
Chaudhari, Chandan,Siddiki, S.M.A. Hakim,Shimizu, Ken-Ichi
, p. 4885 - 4888 (2015/07/28)
Abstract Pt/Al2O3 and Pt/TiO2 were effective catalysts for the synthesis of 2-substituted benzothiazoles and benzimidazoles from 2-aminothiophenol and 1,2-phenylenediamine with alcohols or aldehydes under acceptor-free and additive-free conditions.
Copper-catalyzed solvent-free redox condensation of benzothiazoles with aldehydes or benzylic alcohols
Zhang, Mingliang,Lu, Wen-Ting,Ruan, Wenqing,Zhang, Hui-Jun,Wen, Ting-Bin
, p. 1806 - 1809 (2014/03/21)
An efficient and practical method for the construction of 2-aryl-and 2-alkyl-substituted benzothiazoles via a copper-catalyzed redox condensation process between benzothiazoles and aldehydes or benzylic alcohols has been developed. The reaction proceeded under mild reaction conditions using environmentally benign tert-butyl hydroperoxide (TBHP) as the oxidant. A reaction mechanism involving the ring-opening of benzothiazoles initiated by the attack of acyl radical on the thiazole ring and intramolecular condensation is proposed based on the isolation of an anilide disulfide intermediate.
Eco-friendly atom-economical synthesis of 2-substituted-benzo[d]thiazoles and 2-substituted-benzo[d]oxazoles using 2-acylpyridazin-3(2H)-ones
Sung, Gi Hyeon,Lee, In-Hye,Kim, Bo Ram,Shin, Dong-Soo,Kim, Jeum-Jong,Lee, Sang-Gyeong,Yoon, Yong-Jin
, p. 3530 - 3535 (2013/05/08)
Efficient and green syntheses of heterocycles are of great importance. In this work, we have demonstrated the synthesis of benzo[d]thiazoles and benzo[d]oxazoles using 2-acylpyridazin-3(2H)-ones as acyl transfer agents under transition-metal-free and eco-
Na2S2O4-mediated cyclocondensations of 2,2′-disulfanediyldi- anilines with aldehydes: A facile and inexpensive method for the synthesis of 2-substituted benzothiazoles
Wang, Zhanglin,Tang, Riyuan,Xiao, Qin
experimental part, p. 314 - 320 (2012/01/05)
A facile and inexpensive method for the synthesis of 2-substituted benzothiazoles has been developed by Na2S2O 4-mediated cyclocondensations of 2,2′-disulfanediyldianilines with aldehydes. In the presence of Na2S2O4 and 4 A molecular sieves, a variety of 2-substituted benzothiazoles were obtained from the reaction of 2,2′-disulfanediyldianilines with aldehydes in moderate to high yields. Copyright
