Chemo- and Diastereoselective Synthesis of Spirooxindole-pyrazolines and Pyrazolones via P(NMe2)3-Mediated Substrate-Controlled Annulations of Azoalkenes with α-Dicarbonyl Compounds

被引：8

作者：

Du, Yunfeng ^{[1
]}

Liu, Yuefei ^{[1
]}

Guo, Hongyu ^{[1
]}

Liu, Rongfang ^{[2
]}

Zhou, Rong ^{[1
,3
]}

机构：

[1] Taiyuan Univ Technol, Coll Chem, Taiyuan 030024, Peoples R China

[2] Shanxi Univ Chinese Med, Coll Tradit Chinese Med & Food Engn, Jinzhong 030619, Peoples R China

[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 26期

基金：

中国国家自然科学基金;

关键词：

FACILE SYNTHESIS; CYCLOADDITION; OXINDOLES; ACCESS;

D O I：

10.1021/acs.orglett.3c01348

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

P(NMe2)(3)-mediated substrate-controlledannulationsof azoalkenes with & alpha;-dicarbonyl compounds are reported, wherethe azoalkenes serve as either four or five-atom synthons chemoselectively.The azoalkene participates in annulation with isatins as a four-atomsynthon to furnish the spirooxindole-pyrazolines, whereas it functionsas a novel five-atom synthon in annulation with aroylformates, therebyleading to chemo- and stereoselective formation of pyrazolones. Thesynthetic utilities of the annulations have been demonstrated, anda novel TEMPO-mediated decarbonylation reaction is unveiled.

引用

页码：4776 / 4781

页数：6

共 40 条

[1] Interceptive [4+1] Annulation of in Situ Generated 1,2-Diaza-1,3-dienes with Diazo Esters: Direct Access to Substituted Mono-, Bi-, and Tricyclic 4,5-Dihydropyrazoles [J].

Attanasi, Orazio A. ;

De Crescentini, Lucia ;

Favi, Gianfranco ;

Mantellini, Fabio ;

Mantenuto, Serena ;

Nicolini, Simona .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17) :8331-8338

[2] Synthesis and chemistry of structurally unique hexasubstituted pyrazolines [J].

Baumstark, Alfons L. ;

Vasquez, Pedro C. ;

McTush-Camp, Davita .

HETEROCYCLIC COMMUNICATIONS, 2013, 19 (01) :13-17

[3] Asymmetric synthesis of pyrazoles and pyrazolones employing the reactivity of pyrazolin-5-one derivatives [J].

Chauhan, Pankaj ;

Mahajan, Suruchi ;

Enders, Dieter .

CHEMICAL COMMUNICATIONS, 2015, 51 (65) :12890-12907

[4] Enantioselective Synthesis of Dihydropyrazoles by Formal [4+1] Cycloaddition of in Situ-Derived Azoalkenes and Sulfur Ylides [J].

Chen, Jia-Rong ;

Dong, Wan-Rong ;

Candy, Mathieu ;

Pan, Fang-Fang ;

Joerres, Manuel ;

Bolm, Carsten .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (16) :6924-6927

[5] Application of 3-Alkyl-2-vinylindoles in Catalytic Asymmetric Dearomative (2+3) Cycloadditions [J].

Chen, Ke-Wei ;

Wang, Dan-Dan ;

Liu, Si-Jia ;

Wang, Xue ;

Zhang, Yu-Chen ;

Tian, Yi-Ming ;

Wu, Qiong ;

Shi, Feng .

JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (15) :10427-10439

[6] Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch [J].

Ciccolini, Cecilia ;

Mari, Giacomo ;

Gatti, Francesco G. ;

Gatti, Giuseppe ;

Giorgi, Gianluca ;

Mantellini, Fabio ;

Favi, Gianfranco .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (17) :11409-11425

[7] Cycloadditions and condensations as essential tools in spiropyrazoline synthesis [J].

Dadiboyena, Sureshbabu .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 63 :347-377

[8] Synthesis of spiro-pyrazole-3,3′-thiopyrano[2,3-b]pyridines and azolo[a]pyrido[2′,3′:5,6]thiopyrano[3,4-d]pyrimidines as new ring systems with antifungal and antibacterial activities [J].

Dawood, KM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (02) :221-225

[9]

Farghaly T. A., 2022, POLYCYCL AROMAT COMP, P1

[10] Synthesis of Spiropyrazoles Under Organic and Nonorganic Catalysis [J].

Farghaly, Thoraya A. ;

Al-Hussain, Sami A. ;

Zaki, Magdi E. A. ;

Asghar, Basim H. ;

Muhammad, Zeinab A. .

CURRENT ORGANIC CHEMISTRY, 2022, 26 (09) :834-856

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