A One-Pot, Multicomponent Synthesis of Trifluoromethylated Spiropiperidines under Catalyst-Free Conditions

被引：19

作者：

Shi, Wei ^{[1
]}

Wang, Yang ^{[1
]}

Zhu, Yingjun ^{[1
]}

Zhang, Min ^{[1
]}

Song, Liping ^{[1
,2
]}

Deng, Hongmei ^{[3
]}

机构：

[1] Shanghai Univ, Sch Sci, Dept Chem, 99 Shangda Rd, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China

[3] Shanghai Univ, Lab Microstruct, Shanghai 200444, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 20期

基金：

中国国家自然科学基金;

关键词：

fluorinated heterocycles; Michael addition; spiropiperidines; catalyst-free; multicomponent reactions; 3-COMPONENT SYNTHESIS; CHEMISTRY; ISOXAZOLE; FLUORINE; FACILE; AMINE;

D O I：

10.1055/s-0035-1562433

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient, efficient, one-pot strategy for the synthesis of structurally diverse trifluoromethylated spirotetrahydropyridine-3-carboxylate derivatives is disclosed by taking advantage of a four-component reaction involving arylidene isoxazol-5-ones, aromatic aldehydes, ethyl 4,4,4-trifluoro-3-oxobutanoate and ammonium acetate. Additionally, a more consecutive approach to the same products is achieved via a one-pot, multicomponent reaction. The protocol allows easy access to trifluoromethylated spiroheterocycles in moderate to good yields under mild and catalyst-free conditions.

引用

页码：3527 / 3536

页数：10

共 51 条

[1] Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents [J].

Abdel-Rahman, AH ;

Keshk, EM ;

Hanna, MA ;

El-Bady, SM .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) :2483-2488

[2] Synthesis and evaluation of hexahydropyrrolo[3,4-d]isoxazole-4,6-diones as anti-stress agents [J].

Badru, Rahul ;

Anand, Preet ;

Singh, Baldev .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 48 :81-91

[3] Demonstration of the facile reversibility of fulvene formation [J].

Bandar, Jeffrey S. ;

Coscia, Rockford W. ;

Lambert, Tristan H. .

TETRAHEDRON, 2011, 67 (24) :4364-4370

[4] Converting 9-methyldipyrrinones to 9-H and 9-CHO dipyrrinones [J].

Boiadjiev, Stefan E. ;

Lightner, David A. .

TETRAHEDRON, 2007, 63 (36) :8962-8976

[5] Higher-order multicomponent reactions: beyond four reactants [J].

Brauch, Sebastian ;

van Berkel, Sander S. ;

Westermann, Bernhard .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) :4948-4962

[6] Multicomponent reactions: advanced tools for sustainable organic synthesis [J].

Cioc, Razvan C. ;

Ruijter, Eelco ;

Orru, Romano V. A. .

GREEN CHEMISTRY, 2014, 16 (06) :2958-2975

[7] Quinine-catalyzed asymmetric domino Michael-cyclization reaction for the synthesis of spirocyclic oxindoles bearing two spiro quaternary centers and three consecutive stereocenters. [J].

Cui, Bao-Dong ;

Li, Shi-Wu ;

Zuo, Jian ;

Wu, Zhi-Jun ;

Zhang, Xiao-Mei ;

Yuan, Wei-Cheng .

TETRAHEDRON, 2014, 70 (10) :1895-1902

[8] Iodine catalyzed one-pot multi-component reaction to CF3-containing spiro[indene-2,3′-piperidine] derivatives [J].

Dai, Baifan ;

Duan, Yijun ;

Liu, Xiaoqing ;

Song, Liping ;

Zhang, Min ;

Cao, Weiguo ;

Zhu, Shizheng ;

Deng, Hongmei ;

Shao, Min .

JOURNAL OF FLUORINE CHEMISTRY, 2012, 133 :127-133

[9] Recent developments in asymmetric multicomponent reactions [J].

de Graaff, Corien ;

Ruijter, Eelco ;

Orru, Romano V. A. .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (10) :3969-4009

[10] Synthesis of alkenyldiarylmethanes (ADAMs) containing benzo[d]isoxazole and oxazolidin-2-one rings, a new series of potent non-nucleoside HIV-1 reverse transcriptase inhibitors [J].

Deng, Bo-Liang ;

Zhao, Yujie ;

Hartman, Tracy L. ;

Watson, Karen ;

Buckheit, Robert W., Jr. ;

Pannecouque, Christophe ;

De Clercq, Erik ;

Cushman, Mark .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (03) :1210-1214

← 1 2 3 4 5 6 →