Iodine Promoted One-Pot Synthesis of 2-Aryl Benzoxazoles from Amidoximes via Oxidative Cyclization and Ring Contraction

被引：9

作者：

Zhang, Yong ^{[1
]}

Ji, Min ^{[1
]}

机构：

[1] Southeast Univ, Sch Biol Sci & Med Engn, Dingjiaqiao 87, Nanjing 210009, Jiangsu, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 45期

基金：

中国国家自然科学基金;

关键词：

Amidoximes; 2-Aryl benzoxazoles; Iodine; Oxidative cyclization; Ring contraction; C-H BOND; INTRAMOLECULAR O-ARYLATION; DIARYLIODONIUM SALTS; CATALYZED ARYLATION; 2-ARYLBENZOXAZOLES; COMPLEXES; EFFICIENT; ARYL; BENZOTHIAZOLES; TRANSFORMATION;

D O I：

10.1002/ejoc.201901468

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A molecular I-2-promoted one-pot synthesis of 2-aryl benzoxazoles has been developed by using amidoximes rather than the limited 2-aminophenols or 2-haloamides as substrates. The amidoxime substrates provided unique and efficient strategies for converting readily available aniline and benzaldehyde precursors into valuable chemicals. This transformation proceeded smoothly under transition-metal-free conditions through a sequential oxidative cyclization and ring contraction, and provided a potential route for introducing certain groups at any site of the scaffold.

引用

页码：7506 / 7510

页数：5

共 50 条

[1] TEMPO-mediated aerobic oxidative synthesis of 2-aryl benzoxazoles via ring-opening of benzoxazoles with benzylamines
Rao, Mugada Sugunakara
Hussain, Sahid
[J]. SYNTHETIC COMMUNICATIONS, 2021, 51 (17) : 2684 - 2694
[2] A One-Pot Three-Step Strategy Enables Robust and Efficient Synthesis of 2-Aryl Benzoxazoles from Amides
Huang, Bomao
Zhang, Xinlan
Guo, Yue
Tie, Shaolong
Yang, Dingqiao
Li, Yue
[J]. CHEMISTRYSELECT, 2022, 7 (34):
[3] Iodine-Promoted Oxidative Cyclization of Methyl Azaarenes and α-Amino Ketones for One-Pot Synthesis of 2-Azaaryl-5-aryl Oxazoles
Zhu, Yan-Ping
Zhou, Yu
Li, Wen-Juan
Liu, Fu-Rao
Wang, Wen-Cheng
Hao, Kai-Yan
Chao, Bing-Yu
Shi, Tian-Ru
Wu, An-Xin
Sun, Yuan-Yuan
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (18): : 12460 - 12469
[4] One-pot Synthesis of 2-Substituted Benzoxazoles Promoted by Copper Acetate Monohydrate
Chen, Guo-Feng
Shen, Hai-Dong
Zhang, Li-Yan
Li, Hong-Yang
Lan, Rui-Jia
Chen, Bao-Hua
Li, Ji-Tai
Hu, Qing-Hui
[J]. LETTERS IN ORGANIC CHEMISTRY, 2014, 11 (03) : 180 - 187
[5] Synthesis of 2-Aryl Benzoxazoles from Benzoxazoles and α-Ketoic Acids by Photoredox Catalysis
Li, Yadong
Wu, Pengju
Yang, Zhiyong
[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (06) : 1770 - 1777
[6] "One-pot" access to dihydrofurans via tandem oxidative difunctionalization and ring contraction of aminopyrans
Mandha, Santhosh Reddy
Alla, Manjula
Nanubolu, Jagadeesh Babu
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (25) : 4412 - 4420
[7] CuI-catalyzed and air promoted oxidative cyclization for one-pot synthesis of polyarylated oxazoles
Hu, Ping
Wang, Qiang
Yan, Yizhe
Zhang, Shuai
Zhang, Baiqun
Wang, Zhiyong
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (26) : 4304 - 4307
[8] TBHP/KI-Promoted Oxidative Cyclization of α-Aminoketones for One-Pot Synthesis of Substituted 2-Acyloxazoles
Zheng, Jiecheng
Zhu, Dali
Yang, Zhangyou
Chen, Huali
Wang, Wei
Gan, Lin Ling
Gan, Zongjie
[J]. SYNTHESIS-STUTTGART, 2023, 55 (09): : 1419 - 1426
[9] KMnO4/HOAc system promoted one-pot synthesis of benzoxazoles from o-aminophenols or oxidative cyclization of o-hydroxyarylidene anilines at room temperature
Mirjalili, B. F.
Bamoniri, A.
Bagheri, E.
[J]. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2016, 13 (05) : 809 - 814
[10] Catalyst-free, One-pot Synthesis of 2-Aryl Benzimidazoles from Ortho-phenylenediamine and Aryl Aldehyde in Acetonitrile
Khatik, Gopal L.
[J]. LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (12) : 1070 - 1076

← 1 2 3 4 5 →