Three-component domino reactions providing rapid and efficient routes to fully substituted pyrroles

被引：16

作者：

Liu, Jia-Yan ^{[1
]}

Li, Qiu-Yun ^{[1
]}

Jiang, Bo ^{[1
]}

Tu, Shu-Jiang ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou, Jiangsu, Peoples R China

来源：

RSC ADVANCES | 2013年 / 3卷 / 15期

关键词：

ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; CYCLIZATION REACTIONS; ULTRAVIOLET-SPECTRA; CATALYZED REACTION; ORGANIC-SYNTHESIS; ATOM ECONOMY; CYCLOADDITION; ENAMINONES; ACID;

D O I：

10.1039/c3ra40252e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New indolation and thiolation-based three-component domino reactions, promoted by Bronsted acid, have been described, and 49 examples of polyfunctionalized fully substituted pyrroles were synthesized in good to excellent yields. The reactions were further expanded to prepare multi-functionalized 4,5-dihydro-1H-pyrroles with high stereoselectivity when an aromatic amine was used as a monodonor component. The reaction is easy to perform by simply mixing three common reactants in acetic acid under microwave heating. The reaction proceeds with a fast rate and can be finished within 26 min, the workup is also convenient.

引用

页码：5056 / 5068

页数：13

共 97 条

[1] Two Titanium-Catalyzed Reaction Sequences for Syntheses of Pyrroles from (E/Z)-Chloroenynes or α-Haloalkynols [J].

Ackermann, Lutz ;

Sandmann, Rene ;

Kaspar, Ludwig T. .

ORGANIC LETTERS, 2009, 11 (09) :2031-2034

[2] Antitumor imidazotetrazines. 41. Conjugation of the antitumor agents mitozolomide and temozolomide to peptides and lexitropsins bearing DNA major and minor groove-binding structural motifs [J].

Arrowsmith, J ;

Jennings, SA ;

Clark, AS ;

Stevens, MFG .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (25) :5458-5470

[3] USE OF BORON-TRIFLUORIDE ETHERATE IN THE PREPARATION OF 2-AMINO-1-ALKENYL KETONES FROM BETA-DIKETONES AND LOW-BOILING AMINES [J].

AZZARO, M ;

GERIBALDI, S ;

VIDEAU, B .

SYNTHESIS-STUTTGART, 1981, (11) :880-881

[4]

Ballini R., 2001, SYNTHESIS-STUTTGART, P2003

[5] Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot Sila-Stetter/Paal-Knorr strategy [J].

Bharadwaj, AR ;

Scheidt, KA .

ORGANIC LETTERS, 2004, 6 (14) :2465-2468

[6] 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

[7] One-pot three-component catalytic synthesis of fully substituted pyrroles from readily available propargylic alcohols, 1,3-dicarbonyl compounds and primary amines [J].

Cadierno, Victorio ;

Gimeno, Jose ;

Nebra, Noel .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (35) :9973-9981

[8] SELECTIVITY IN BETA-ENAMINO KETONE ANION GENERATION AND ALKYLATION [J].

CHEN, YL ;

MARIANO, PS ;

LITTLE, GM ;

OBRIEN, D ;

HUESMANN, PL .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (23) :4643-4654

[9] TRICYCLIC HETEROAROMATIC SYSTEMS - [1]BENZOPYRANOPYRROL-4-ONES AND [1]BENZOPYRANO-1,2,3-TRIAZOL-4-ONES AS BENZODIAZEPINE RECEPTOR LIGANDS - SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].

COLOTTA, V ;

CECCHI, L ;

MELANI, F ;

FILACCHIONI, G ;

MARTINI, C ;

GIANNACCINI, G ;

LUCACCHINI, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2646-2651

[10]

COONEY JV, 1981, J ORG CHEM, V46, P2570, DOI 10.1021/jo00325a027

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