Iron-Catalyzed Inexpensive and Practical Synthesis of N-Substituted Pyrroles in Water

被引：92

作者：

Azizi, Najmedin ^{[1
]}

Khajeh-Amiri, Alireza ^{[1
]}

Ghafuri, Hossein ^{[2
]}

Bolourtchian, Mohammad ^{[1
]}

Saidi, Mohammad Reza ^{[2
]}

机构：

[1] Chem & Chem Engn Res Ctr Iran, Tehran, Iran

[2] Sharif Univ Technol, Dept Chem, Tehran 11365, Iran

来源：

SYNLETT | 2009年 / 14期

关键词：

dimethoxytetrahydrofuran; iron; pyrrole; amine; water chemistry; SOLID-PHASE SYNTHESIS; ONE-POT SYNTHESIS; SOLVENT-FREE; INDOLES; CONDENSATION; PRECURSORS; ALKYLATION; ALKYNES; AMINES;

D O I：

10.1055/s-0029-1217799

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An operationally simple, practical, and economical protocol for iron(III) chloride catalyzed Paal-Knorr pyrrole synthesis in water in good to excellent yields has been developed. Several N-substituted pyrroles are readily prepared from the reaction of 2,5-dimethoxytetrahydrofuran and aryl/alkyl, sulfonyl and acyl amines under very mild reaction conditions

引用

收藏

页码：2245 / 2248

页数：4

相关论文

共 61 条

[1] Triflic acid-catalyzed highly stereoselective friedel-crafts aminoalkylation of indoles and pyrroles [J].

Abid, Mohammed ;

Teixeira, Liliana ;

Torok, Bela .

ORGANIC LETTERS, 2008, 10 (05) :933-935

[2] Triflic acid controlled successive annelation of aromatic sulfonamides:: an efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles [J].

Abid, Mohammed ;

Teixeira, Liliana ;

Torok, Bela .

TETRAHEDRON LETTERS, 2007, 48 (23) :4047-4050

[3] Solvent-free solid acid-catalyzed electrophilic annelations:: A new green approach for the synthesis of substituted five-membered N-heterocycles [J].

Abid, Mohammed ;

Spaeth, Andrew ;

Torok, Bela .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) :2191-2196

[4] 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

[5]

AZIZ N, 2003, J ORG CHEM, P4630

[6] One-pot synthesis of dithiocarbamates accelerated in water [J].

Azizi, N ;

Aryanasab, F ;

Torkiyan, L ;

Ziyaei, A ;

Saidi, MR .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09) :3634-3635

[7] Highly efficient one-pot three-component Mannich reaction in water catalyzed by heteropoly acids [J].

Azizi, N ;

Torkiyan, L ;

Saidi, MR .

ORGANIC LETTERS, 2006, 8 (10) :2079-2082

[8] Highly chemoselective addition of amines to epoxides in water [J].

Azizi, N ;

Saidi, MR .

ORGANIC LETTERS, 2005, 7 (17) :3649-3651

[9] Novel and efficient method for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS) under solvent-free and neutral conditions [J].

Azizi, N ;

Saidi, MR .

ORGANOMETALLICS, 2004, 23 (06) :1457-1458

[10] LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions [J].

Azizi, N ;

Saidi, MR .

TETRAHEDRON, 2004, 60 (02) :383-387

← 1 2 3 4 5 6 7 →