Divergent Synthesis of 3,5-Disubstituted Pyrazoles and α, β-Alkynic Hydrazone from Diarylpropynones and Carbazates

被引：4

作者：

Wang, Qi ^{[1
,2
]}

Hong, Gang ^{[1
,2
]}

Tang, Zhicong ^{[1
,2
]}

Yang, Peng ^{[1
,2
]}

Zhong, Yi ^{[1
,2
]}

Gong, Yu ^{[1
,2
]}

Wang, Limin ^{[1
,2
]}

机构：

[1] East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China

[2] East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Feringa Nobel Prize Scientist Joint Res Ctr, 130 Meilong Rd, Shanghai 200237, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 11卷 / 02期

基金：

中国国家自然科学基金;

关键词：

alpha; beta-alkynic hydrazone; cyclization; heterocycles; pyrazoles Yb(OTf)(3); ONE-POT SYNTHESIS; N-ALKYLATED TOSYLHYDRAZONES; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; ACETYLENIC KETONES; TERMINAL ALKYNES; SUBSTITUTED PYRAZOLES; 3-COMPONENT SYNTHESIS; DIACETYLENIC KETONES; DERIVATIVES;

D O I：

10.1002/ajoc.202100794

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Yb(OTf)(3) catalyzed synthesis of pyrazoles by cyclization of 1,3-diarylpropynones with carbazates was reported. In the presence of K2S2O8/TBAI as catalyst, alpha,beta-alkynic hydrazone was obtained through the reactions from the same starting materials in up to 97% yields. Mechanistic studies indicated that propargyl hydrazone was not involved in pyrazole formation. The aggregation-induced emission (AIE) characteristics of the pyrazoles were explored, demonstrating potential applications in the luminophoric materials.

引用

页数：5

共 87 条

[1] Practical routes to diacetylenic ketones and their application for the preparation of alkynyl substituted pyridines, pyrimidines and pyrazoles [J].