A Novel Synthesis of Multisubstituted Pyrroles via Trisubstituted Olefins and TosMIC Derivatives

被引：5

作者：

Qiu, Fangli ^{[1
,2
]}

Wu, Jianwei ^{[1
]}

Zhang, Yaohong ^{[1
]}

Hu, Miao ^{[1
]}

Yu, Feng ^{[3
]}

Zhang, Guolin ^{[1
]}

Yu, Yongping ^{[1
]}

机构：

[1] Zhejiang Univ, Coll Pharmaceut Sci, Hangzhou 310058, Zhejiang, Peoples R China

[2] Taizhou Univ, Coll Pharmaceut & Chem Engn, Taizhou 317000, Peoples R China

[3] Zhejiang Chem Ind Res Inst, Hangzhou 310058, Zhejiang, Peoples R China

来源：

LETTERS IN ORGANIC CHEMISTRY | 2012年 / 9卷 / 04期

基金：

中国国家自然科学基金;

关键词：

p-toluenesulfonylmethyl isocyanide(TosMIC); trisubstituted olefins; multisubstituted pyrrole; heterocycles; derivatives; HIGHLY REGIOSELECTIVE SYNTHESIS; SULFONYLMETHYL ISOCYANIDES; POLYSUBSTITUTED PYRROLES; BIOLOGICAL EVALUATION; CHEMISTRY; CYCLOADDITION; SUBSTITUENTS; ALKALOIDS;

D O I：

10.2174/157017812800233778

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel synthesis of multisubstituted pyrroles was developed where in trisubstituted olefins were reacted with p-toluenesulfonylmethyl isocyanide (TosMIC) derivatives. The entire process is operationally simplistic and utilizes mild reaction conditions. Additionally a possible mechanism is proposed.

引用

页码：305 / 308

页数：4

共 46 条

[1]

[Anonymous], 1997, ELECT MAT OLIGOMER A

[2] An Extremely Facile Synthesis of Furans, Pyrroles, and Thiophenes by the Dehydrative Cyclization of Propargyl Alcohols [J].

Aponick, Aaron ;

Li, Chuan-Ying ;

Malinge, Jeremy ;

Marques, Emerson Finco .

ORGANIC LETTERS, 2009, 11 (20) :4624-4627

[3] A Base-Catalysed One-Pot Three-Component Coupling Reaction Leading to Nitrosubstituted Pyrroles [J].

Baxendale, Ian R. ;

Buckle, Christopher D. ;

Ley, Steven V. ;

Tamborini, Lucia .

SYNTHESIS-STUTTGART, 2009, (09) :1485-1493

[4] Efficient synthesis of highly substituted pyrroles based on the tandem reactions: intermolecular amination and Pd(II)-catalyzed intramolecular hydroamidation [J].

Bian, Yong-Jiang ;

Liu, Xue-Yuan ;

Ji, Ke-Gong ;

Shu, Xing-Zhong ;

Guo, Li-Na ;

Liang, Yong-Min .

TETRAHEDRON, 2009, 65 (07) :1424-1429

[5] Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels-Alder reactions [J].

Boger, DL ;

Boyce, CW ;

Labroli, MA ;

Sehon, CA ;

Jin, Q .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) :54-62

[6] Synthesis and SAR of 4-(3-hydroxyphenylamino)pyrrolo-[2,1-f][1,2,4]triazine based VEGFR-2 kinase inhibitors [J].

Borzilleri, RM ;

Cai, ZW ;

Ellis, C ;

Fargnoli, J ;

Fura, A ;

Gerhardt, T ;

Goyal, B ;

Hunt, JT ;

Mortillo, S ;

Qian, LG ;

Tokarski, J ;

Vyas, V ;

Wautlet, B ;

Zheng, XP ;

Bhide, RS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (05) :1429-1433

[7] An approach to the Paal-Knorr pyrroles synthesis catalyzed by Sc(OTf)3 under solvent-free conditions [J].

Chen, Jiuxi ;

Wu, Huayue ;

Zheng, Zhiguo ;

Jin, Can ;

Zhang, Xingxian ;

Su, Weike .

TETRAHEDRON LETTERS, 2006, 47 (30) :5383-5387

[8] Study on photochromism of diarylethenes with a 2,5-dihydropyrrole bridging unit: A convenient preparation of 3,4-diarylpyrroles from 3,4-diaryl-2,5-dihydropyrroles [J].

Chen, Y ;

Zeng, DX ;

Xie, N ;

Dang, YZ .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) :5001-5005

[9] Diradical dications of m- and p-phenylenebis[2,5-di(2-thienyl)-1-pyrrole]:: Weakly coupled diradicals [J].

Domingo, VM ;

Alemán, C ;

Brillas, E ;

Juliá, L .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) :4058-4061

[10] Highly Regioselective Synthesis of Polysubstituted Pyrroles through Three-Component Reaction Induced by Low-Valent Titanium Reagent [J].

Dou, Guolan ;

Shi, Chunling ;

Shi, Daqing .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (06) :810-813

← 1 2 3 4 5 →