I2-Mediated Oxidative C-N Bond Formation for Metal-Free One-Pot Synthesis of Di-, Tr-, and Tetrasubstituted Pyrazoles from α,β-Unsaturated Aldehydes/Ketones and Hydrazines

被引：132

作者：

Zhang, Xinting ^{[1
]}

Kang, Jinfeng ^{[1
]}

Niu, Pengfei ^{[1
]}

Wu, Jie ^{[1
]}

Yu, Wenquan ^{[1
]}

Chang, Junbiao ^{[1
]}

机构：

[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Henan Province, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 21期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

REGIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATION; SUBSTITUTED PYRAZOLES; CATALYZED AMINATION; ANTIFUNGAL ACTIVITY; MEDIATED OXIDATION; DERIVATIVES; INHIBITORS; EFFICIENT; DESIGN;

D O I：

10.1021/jo501844x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An I-2-mediated metal-free oxidative CN bond formation methodology has been established for the regioselective pyrazole synthesis. This practical and eco-friendly one-pot protocol requires no isolation of the less stable intermediates hydrazones and provides a facile access to a variety of di-, tri-, and tetrasubstituted (aryl, alkyl, and/or vinyl) pyrazoles from readily available alpha,beta-unsaturated aldehydes/ketones and hydrazine salts.

引用

页码：10170 / 10178

页数：9

共 17 条

[1] Intramolecular oxidative C-N bond formation under metal-free conditions: One-pot global functionalization of pyrazole ring
Tiwari, Mohit K.
Iqubal, Ashif
Das, Parthasarathi
TETRAHEDRON, 2022, 126
[2] Iodine-mediated C-N and N-N bond formation: a facile one-pot synthetic approach to 1,2,3-triazoles under metal-free and azide-free conditions
Mani, Geeta Sai
Donthiboina, Kavitha
Shaik, Siddiq Pasha
Shankaraiah, Nagula
Kamal, Ahmed
RSC ADVANCES, 2019, 9 (46) : 27021 - 27031
[3] Metal-Free C-N- and N-N-Bond Formation: Synthesis of 1,2,3-Triazoles from Ketones, N-Tosylhydrazines, and Amines in One Pot
Chen, Zhengkai
Yan, Qiangqiang
Liu, Zhanxiang
Zhang, Yuhong
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) : 17635 - 17639
[4] I2-Mediated Oxidative C-O Bond Formation for the Synthesis of 1,3,4-Oxadiazoles from Aldehydes and Hydrazides
Yu, Wenquan
Huang, Gang
Zhang, Yueteng
Liu, Hongxu
Dong, Lihong
Yu, Xuejun
Li, Yujiang
Chang, Junbiao
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) : 10337 - 10343
[5] A one pot, metal-free, three-component domino sequence for the synthesis of furans: an efficient C-O and C-N bond formation approach
Guo, Pengfeng
Wang, Changcheng
Chen, Ya
Ou, Caijun
Jiang, Hangqi
Chen, Weifeng
Chen, Weixin
Cao, Hua
RSC ADVANCES, 2016, 6 (46): : 39563 - 39567
[6] TsNBr2 promoted cascade formation of C-N and C-S bond: Metal-free synthesis of 2-aminothiazoles from ketones or ketoximes using thiourea
Loukrakpam, Dineshwori Chanu
Mishra, Debashish
Begum, Jurima
Phukan, Prodeep
TETRAHEDRON, 2023, 149
[7] One-Pot Synthesis of 3-Aryl-5-amino-1,2,4-thiadiazoles from Imidates and Thioureas by I2-Mediated Oxidative Construction of the N-S Bond
Chai, Ling
Lai, Zhenzhen
Xia, Qiangqiang
Yuan, Jiangpei
Bian, Qilong
Yu, Mingjian
Zhang, Wenkai
Xu, Yuanqing
Xu, Hao
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (31) : 4338 - 4344
[8] I2-Mediated Oxidative C-N and N-S Bond Formation in Water: A Metal-Free Synthesis of 4,5-Disubstituted/N-Fused 3-Amino-1,2,4-triazoles and 3-Substituted 5-Amino-1,2,4-thiadiazoles
Jatangi, Nagesh
Tumula, Nagaraju
Palakodety, Radha Krishna
Nakka, Mangarao
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (10) : 5715 - 5723
[9] An Efficient One-Pot Multicomponent Synthesis of Tetracyclic Quinazolino[4,3-b]quinazolines by Sequential C-N Bond Formation and Copper-Mediated Aerobic Oxidative Cyclization
Potuganti, Gal Reddy
Indukuri, Divakar Reddy
Alla, Manjula
SYNLETT, 2018, 29 (13) : 1717 - 1722
[10] One-Pot Regiospecific Synthesis of Imidazo[1,2-a]pyridines: A Novel, Metal-Free, Three-Component Reaction for the Formation of C-N, C-O, and C-S Bonds
Cao, Hua
Liu, Xiaohang
Zhao, Limin
Cen, Jinghe
Lin, Jingxin
Zhu, Qiuxia
Fu, Minling
ORGANIC LETTERS, 2014, 16 (01) : 146 - 149

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