835-71-2Relevant articles and documents
DMF-Assisted Radical Cyclization of o-Isocyanodiaryl Ethers via 1,5-Aryl Migration: Construction of 2-Arylbenzoxazoles
Cai, Jingyu,Ding, Qiuping,Peng, Yiyuan,Song, Zhibin,Tan, Yuxing,Ye, Xiaoling,Yuan, Sitian
, p. 1485 - 1492 (2022/01/20)
A novel DMF-assisted radical cyclization of o-isocyanodiaryl ethers via 1,5-aryl migration has been developed for the synthesis of a series of 2-arylbenzoxazoles by the FeCl3/TBHP/Et3N catalytic system in DMF. However, N,N-dimethylbenzo[d]thiazole-2-carboxamide and N,N-dimethylbenzo[d]selenazole-2-carboxamide were obtained from the corresponding substrate 2-isocyanophenyl p-methoxyphenyl thioether and 2-isocyanodiphenyl selenoether under the same conditions. A possible mechanism may involve aryl 1,5-migration and DMF-assisted radical cyclization of o-isocyanodiaryl ethers.
Investigation of Pd-PEPPSI catalysts and coupling partners towards direct C2-arylation/heteroarylation of benzoxazole
Gokanapalli, Anusha,Motakatla, Venkata Krishna Reddy,Peddiahgari, Vasu Govardhana Reddy
, (2021/05/13)
2-Aryl/heteroaryl-substituted benzoxazoles are important heterocyclic motifs extensively found in several bioactive molecules, pharmaceuticals and natural products. In view of the importance of these compounds, there is need to develop easiest and simplest synthetic routes. The motive of this current work is to conduct the direct C2-arylation reaction on benzoxazole with various cross-coupling partners like aryl/heteroaryl halide/carboxylic acid/diazonium tetrafluoroborate/sulfonyl chloride/boronic acids in the presence of different symmetrical and unsymmetrical Pd-PEPPSI (pyridine-enhanced pre-catalyst preparation by stabilization initiation) catalysts via C (sp2)–C (sp2) bond formation. Compared with other coupling partners, boronic acids coupled with benzoxazole very efficiently in the presence of sterically and electronically tunable bulky1,3-bis(N,N′-2,4,6-triisopropylbenzyl)benzimidazolium-Pd-PEPPSI complex in open air to offer the corresponding C2-aryl/heteroaryl benzoxazole compounds. Further, it is worthy to mention that there is no need of any external oxidant/ligand/additive for the complete conversion of starting molecules to products. The reactions progressed successfully with a wide range of substrate scope and attained the products in good to excellent yields in a short reaction time in ethanol/water (1:1) medium. Greatly, catalysts can be recovered and reused for few cycles with significant reactivity.
An efficient rapid synthesis of benzoxazoles and benzothiazoles using pma.Sio2 at room temperature under heterogeneous conditions
Sudhakar, Chithaluri,Shekhar, Vanam,Shyamsunder, Manchi,Suryakumari, Adurthi,Manojkumar, Vala
, p. 583 - 587 (2021/09/30)
Treatment of 2-aminophenol (or 2-aminothiophenol) with aromatic aldehydes in the presence of phosphomolybdic acid on silica at room temperature affords the corresponding benzoxazoles (or benzothiazoles) in excellent yields (88-96%) under heterogeneous conditions. Benzoxazoles and benzothiazoles are formed in less than 10 min.