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

[21]

DEMINA MM, 1981, ZH OBSHCH KHIM+, V51, P366

[22] Regioselective synthesis of 1,3,5-tri- and 1,3,4,5-tetrasubstituted pyrazoles from N-arylhydrazones and nitroolefins [J].

Deng, Xiaohu ;

Mani, Neelakandha S. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06) :2412-2415

[23] Reaction of N-monosubstituted hydrazones with nitroolefins:: A novel regioselective pyrazole synthesis [J].

Deng, Xiaohu ;

Mani, Neelakandha S. .

ORGANIC LETTERS, 2006, 8 (16) :3505-3508

[24] Triplet 1,3-diphenylpropynylidene (Ph-C-C-C-Ph) [J].

DePinto, Jeffrey T. ;

deProphetis, Wendy A. ;

Menke, Jessica L. ;

McMahon, Robert J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (08) :2308-2315

[25] α-(N-carbamoyl)alkylcuprate chemistry in the synthesis of nitrogen heterocycles [J].

Dieter, RK ;

Lu, K .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (03) :847-855

[26] Regioselective synthesis of 4-(2-alkyl-5-methyl-2H-pyrazol-3-yl)-piperidines [J].

Dirat, O ;

Clipson, A ;

Elliott, JM ;

Garrett, S ;

Jones, AB ;

Reader, M ;

Shaw, D .

TETRAHEDRON LETTERS, 2006, 47 (11) :1729-1731

[27] First synthesis of a bromonitrilimine. Direct formation of 3-bromopyrazole derivatives [J].

Foti, F ;

Grassi, G ;

Risitano, F .

TETRAHEDRON LETTERS, 1999, 40 (13) :2605-2606

[28] The use of tosylhydrazone salts as a safe alternative for handling diazo compounds and their applications in organic synthesis [J].

Fulton, JR ;

Aggarwal, VK ;

de Vicente, J .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (08) :1479-1492

[29] Synthesis of New Fluorinated Tebufenpyrad Analogs with Acaricidal Activity Through Regioselective Pyrazole Formation [J].

Fustero, Santos ;

Roman, Raquel ;

Sanz-Cervera, Juan F. ;

Simon-Fuentes, Antonio ;

Bueno, Jorge ;

Villanova, Salvador .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) :8545-8552

[30] Improved regioselectivity in pyrazole formation through the use of fluorinated alcohols as solvents:: Synthesis and biological activity of fluorinated Tebufenpyrad analogs [J].

Fustero, Santos ;

Roman, Raquel ;

Sanz-Cervera, Juan F. ;

Simon-Fuentes, Antonio ;

Cunat, Ana C. ;

Villanova, Salvador ;

Murguia, Marcelo .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3523-3529

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