1747-46-2Relevant articles and documents
The Construction of C-N, C-O, and C(sp2)-C(sp3) Bonds from Fluorine-Substituted 2-Aryl Benzazoles for Direct Synthesis of N-, O-, C-Functionalized 2-Aryl Benzazole Derivatives
Zhou, Quan,Hong, Xi,Cui, He-Zhen,Huang, Shuang,Yi, Ying,Hou, Xiu-Feng
, p. 6363 - 6372 (2018)
Herein, a general and practical route to 2-(2-aminophenyl)- and 2-(2-alkoxyphenyl)-substituted benzazoles by nucleophilic aromatic substitution (SNAr) is described. Upon treatment with Cs2CO3, the formation of C-N, C-O bonds occur between fluorine-substituted 2-aryl benzazoles and a diverse range of nitrogen, oxygen nucleophiles to provide the targets in good to excellent yields. Commercially available nucleophiles and high atom economy are notable features of the protocol. Meanwhile, the construction of C(sp2)-C(sp3) bond was also furnished in the presence of palladium catalyst.
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.
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.