Morita-Baylis-Hillman acetates of acetylenic aldehydes: versatile synthons for substituted pyrroles via a metal-free tandem reaction

被引：29

作者：

Reddy, Chada Raji ^{[1
]}

Reddy, Motatipally Damoder ^{[1
]}

Srikanth, Boinapally ^{[1
]}

Prasad, Kothakonda Rajendra ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500607, Andhra Pradesh, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 17期

关键词：

POLYSUBSTITUTED PYRROLES; ONE-POT; EFFICIENT SYNTHESIS; ROUTE; CYCLIZATION; ALKALOIDS; CHEMISTRY; ADDUCTS; IMINES; ESTERS;

D O I：

10.1039/c1ob05402c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and metal-free access to 1,2,4-tri or 1,2,4,5-tetrasubstituted pyrroles has been developed by the reaction of Morita-Baylis-Hillman acetates of acetylenic aldehydes with amines and sulfonamides. This new protocol is based on K2CO3-promoted tandem allylic substitution/cycloisomerization reactions.

引用

页码：6027 / 6033

页数：7

共 59 条

[1] Correlation between pKa and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction:: Discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope [J].

Aggarwal, VK ;

Emme, I ;

Fulford, SY .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :692-700

[2] Pyrrole syntheses by multicomponent coupling reactions [J].

Balme, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6238-6241

[3] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[4] A Facile Synthesis of Substituted Indenones and Piperidine-2,6-diones from the Baylis-Hillman Acetates [J].

Basavaiah, Deevi ;

Lenin, Dandamudi V. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (29) :5650-5658

[5] Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry [J].

Basavaiah, Deevi ;

Reddy, Bhavanam Sekhara ;

Badsara, Satpal Singh .

CHEMICAL REVIEWS, 2010, 110 (09) :5447-5674

[6]

Baylis A. B., 1972, CHEM ABSTR 34174Q, V77

[7]

Baylis A. B., 1972, German Pat, Patent No. 2155113

[8] Gold(I)-Catalyzed Cyclization of β-Allenylhydrazones: An Efficient Synthesis of Multisubstituted N-Aminopyrroles [J].

Benedetti, Erica ;

Lemiere, Gilles ;

Chapellet, Laure-Lise ;

Penoni, Andrea ;

Palmisano, Giovanni ;

Malacria, Max ;

Goddard, Jean-Philippe ;

Fensterbank, Louis .

ORGANIC LETTERS, 2010, 12 (19) :4396-4399

[9] 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

[10] Two-Component Approach Toward a Fully Substituted N-Fused Pyrrole Ring [J].

Chernyak, Dmitri ;

Skontos, Cathy ;

Gevorgyan, Vladimir .

ORGANIC LETTERS, 2010, 12 (14) :3242-3245

← 1 2 3 4 5 6 →