One-Step Route to 2,3-Diaminopyrroles Using a Titanium-Catalyzed Four-Component Coupling

被引：47

作者：

Barnea, Eyal ^{[1
]}

Majumder, Supriyo ^{[1
]}

Staples, Richard J. ^{[1
]}

Odom, Aaron L. ^{[1
]}

机构：

[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

来源：

ORGANOMETALLICS | 2009年 / 28卷 / 13期

基金：

美国国家科学基金会;

关键词：

NONACTIVATED TERMINAL ALKYNES; ETHYLENE POLYMERIZATION; HYDROAMINATION; DERIVATIVES; COMPLEXES; HETEROCYCLES; ZIRCONIUM; IMINES;

D O I：

10.1021/om9001928

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A simple indolyl titanium complex, Ti(NMe2)(2)(Ind(Me2))(2) (1), can be prepared from commercially available reagents,Ti(NMe2)(4) and 2,3-dimethylindole. Indolyl-containing 1 is a catalyst for the selective generation of unusual 2,3-diaminopyrroles from four-component coupling of 2 equiv of an isonitrile, 1 equiv of an arylamine, and 1 equiv of an alkyne in an atom-efficient process. For this study, both terminal and internal alkynes were used with a selection of arylamines to provide 11 examples of 2,3-diaminopyrroles. Yields for terminal alkyne substrates in this reaction were 75-93%. In all cases, terminal alkynes result in one or the alpha-positions on the pyrrole being unsubstituted. Two reactions with internal alkynes provided pentasubstituted pyrroles in 42% and 88% yield. Catalyst 1, along with six of the pyrrole products, was structurally characterized by single-crystal X-ray diffraction.

引用

页码：3876 / 3881

页数：6

共 59 条

[31] Synthesis of triazoles from nonactivated terminal alkynes via the three-component coupling reaction using a Pd(0)-Cu(I) bimetallic catalyst [J].

Kamijo, S ;

Jin, TN ;

Huo, ZB ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) :7786-7787

[32] Cyclic 1,3-dipoles or acyclic phosphonium ylides? Electronic characterization of "montrealones" [J].

Krenske, Elizabeth H. ;

Houk, K. N. ;

Arndtsen, Bruce A. ;

St. Cyr, Daniel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (31) :10052-+

[33] Group-4 η1-pyrrolyl complexes incorporating N,N-di(pyrrolyl-α-methyl)-N-methylamine [J].

Li, YH ;

Turnas, A ;

Ciszewski, JT ;

Odom, AL .

INORGANIC CHEMISTRY, 2002, 41 (24) :6298-6306

[34] Palladium catalyzed synthesis of munchnones from α-amidoethers:: A mild route to pyrroles [J].

Lu, Yingdong ;

Arndtsen, Bruce A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (29) :5430-5433

[35]

LYSHCHIKOV AN, 2000, CHEM HETEROCYCL COMP, V36, P532

[36]

Majumder S., UNPUB

[37] Deprotonated diindolylmethanes as dianionic analogues of scorpionate bis(pyrazolyl)borate ligands: synthesis and structural characterization of representative titanocene and zirconocene complexes [J].

Mason, MR ;

Ogrin, D ;

Fneich, B ;

Barnard, TS ;

Kirschbaum, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (01) :157-162

[38] Titanium and zirconium amido complexes ligated by 2,2′-di(3-methylindolyl)methanes:: Synthesis, characterization, and ethylene polymerization activity [J].

Mason, MR ;

Fneich, BN ;

Kirschbaum, K .

INORGANIC CHEMISTRY, 2003, 42 (21) :6592-6594

[39] INTRAMOLECULAR [2+2] CYCLOADDITIONS OF GROUP-IV METAL IMIDO COMPLEXES - APPLICATIONS TO THE SYNTHESIS OF DIHYDROPYRROLE AND TETRAHYDROPYRIDINE DERIVATIVES [J].

MCGRANE, PL ;

JENSEN, M ;

LIVINGHOUSE, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5459-5460

[40] Selectively substituted thiophenes and indoles by a tandem palladium-catalyzed multicomponent reaction [J].

Mitsudo, Koichi ;

Thansandote, Praew ;

Wilhelm, Thorsten ;

Mariampillai, Brian ;

Lautens, Mark .

ORGANIC LETTERS, 2006, 8 (18) :3939-3942

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