La(OTf)3 catalyzed synthesis of α-aryl tetrasubstituted pyrroles through [4+1] annulation under microwave irradiation

被引：16

作者：

Tan, Xue-Min ^{[1
]}

Lai, Qiao-Mei ^{[1
]}

Yang, Zhi-Wei ^{[1
]}

Long, Xiao ^{[1
]}

Zhou, Hai-Lin ^{[1
]}

You, Xiao-Lin ^{[1
]}

Jiang, Xiao-Jie ^{[1
]}

Cui, Hai-Lei ^{[1
]}

机构：

[1] Chongqing Univ Arts & Sci, Int Acad Targeted Therapeut & Innovat, 319 Honghe Ave, Chongqing 402160, Peoples R China

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 02期

基金：

美国国家科学基金会;

关键词：

Annulation; Alkyne; Tetrasubstituted pyrrole; Microwave; Pentasubstituted pyrrole; HIGHLY SUBSTITUTED PYRROLES; POLYSUBSTITUTED PYRROLES; 1,3-DICARBONYL COMPOUNDS; PROPARGYLIC ALCOHOLS; MULTISUBSTITUTED PYRROLES; CHEMOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; CASCADE REACTIONS; TERMINAL ALKYNES; MODULAR APPROACH;

D O I：

10.1016/j.tetlet.2016.11.122

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A La(OTf)(3) catalyzed synthesis of tetrasubstituted pyrroles under microwave irradiation has been developed affording various alpha-aryl tetrasubstituted pyrroles in acceptable to good yields (36-82% yield) through condensation/alkyne azacyclization/isomerization sequence. Functionalized alpha-aryl pentasubstituted pyrroles could be prepared from tetrasubstituted pyrroles through easy transformations. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：163 / 167

页数：5

共 54 条

[1] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[2] Synthesis of Functionalized Pyrroles via Catalyst- and Solvent-Free Sequential Three-Component Enamine-Azoene Annulation [J].

Attanasi, Orazio A. ;

Favi, Gianfranco ;

Mantellini, Fabio ;

Moscatelli, Giada ;

Santeusanio, Stefania .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) :2860-2866

[3] Mitomycinoid Alkaloids: Mechanism of Action, Biosynthesis, Total Syntheses, and Synthetic Approaches [J].

Bass, Phillip D. ;

Gubler, Daniel A. ;

Judd, Ted C. ;

Williams, Robert M. .

CHEMICAL REVIEWS, 2013, 113 (08) :6816-6863

[4] Antimycobacterial compounds. New pyrrole derivatives of BM212 [J].

Biava, M ;

Porretta, GC ;

Deidda, D ;

Pompei, R ;

Tafi, A ;

Manetti, F .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (06) :1453-1458

[5] Antimycobacterial agents. Novel diarylpyrrole derivatives of BM212 endowed with high activity toward mycobacterium tuberculosis and low cytotoxicity [J].

Biava, Mariangela ;

Cesare Porretta, Giulio ;

Poce, Giovanna ;

Supino, Sibilla ;

Deidda, Delia ;

Pompei, Raffaello ;

Molicotti, Paola ;

Manetti, Fabrizio ;

Botta, Maurizio .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (16) :4946-4952

[6] Synthesis of highly substituted pyrroles via a multimetal-catalyzed rearrangement-condensation-cyclization Domino approach [J].

Binder, JT ;

Kirsch, SF .

ORGANIC LETTERS, 2006, 8 (10) :2151-2153

[7] 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

[8] 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

[9] Microwave-Promoted Tin-Free Iminyl Radical Cyclization with TEMPO Trapping: A Practical Synthesis of 2-Acylpyrroles [J].

Cai, Yu ;

Jalan, Ankur ;

Kubosumi, Aaron R. ;

Castle, Steven L. .

ORGANIC LETTERS, 2015, 17 (03) :488-491

[10] Alkylation of 1,3-dicarbonyl compounds with benzylic and propargylic alcohols using Ir-Sn bimetallic catalyst: synthesis of fully decorated furans and pyrroles [J].

Chatterjee, Paresh Nath ;

Roy, Sujit .

TETRAHEDRON, 2011, 67 (25) :4569-4577

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