A novel synthesis of tetra and pentacyclic quinolinopyran tethered pyrazole/coumarin scaffolds via a solid state melt reaction

被引：31

作者：

Bakthadoss, Manickam ^{[1
,2
]}

Kannan, Damodharan ^{[1
]}

机构：

[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India

[2] Pondicherry Univ, Dept Chem, Pondicherry 605014, India

来源：

RSC ADVANCES | 2014年 / 4卷 / 23期

关键词：

DIELS-ALDER REACTIONS; BAYLIS-HILLMAN REACTION; DOMINO REACTIONS; DERIVATIVES; PYRAZOLES; GENERATION; ALKALOIDS; COMPLEX; ACID;

D O I：

10.1039/c3ra46894a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new protocol has been developed for the efficient synthesis of structurally diverse tetra-and pentacyclic quinolinopyran tethered pyrazole/coumarin architectures via a domino Knoevenagel intramolecular hetero-Diels-Alder (IMHDA) strategy using a solid state melt reaction (SSMR) in a highly diastereo and regioselective fashion. Gratifyingly, these heterocyclic frameworks were synthesized under solvent and catalyst free conditions, without the aid of a work-up and column chromatography purification. The generality and functional tolerance of this convergent and environmentally benign method is very attractive.

引用

页码：11723 / 11731

页数：9

共 64 条

[1]

Bakthadoss M., 2012, SYNTHESIS-STUTTGART, V5, P755

[2] Synthesis of Novel Vicinal Coumarin- and Oxindole-Functionalized Dispiropyrrolidines and Dispiropyrrolizidines via [3+2]-Cycloaddition Reactions [J].

Bakthadoss, Manickam ;

Kannan, Damodharan ;

Sivakumar, Govindan .

SYNTHESIS-STUTTGART, 2012, 44 (05) :793-799

[3] First Friedel-Crafts Reaction of the Baylis-Hillman Adducts Derived from Nitroolefins: Application towards Synthesis of Pyrrolidines and Spiropyrrolidines [J].

Bakthadoss, Manickam ;

Sivakumar, Nagappan .

SYNLETT, 2011, (09) :1296-1302

[4] First Synthesis of Bromo and Chloro Derivatives of Baylis-Hillman Adducts Derived from Nitroolefins: Application towards the Synthesis of a Dendrimer Core [J].

Bakthadoss, Manickam ;

Sivakumar, Nagappan ;

Devaraj, Anthonisamy .

SYNTHESIS-STUTTGART, 2011, (04) :611-618

[5] Highly Stereoselective Synthesis of Tricyclic Chromenoisoxazolidines by Intramolecular 1,3-Dipolar Cycloadditions [J].

Bakthadoss, Manickam ;

Murugan, Gandhi .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (30) :5825-5830

[6] Solid-State Melt Reaction for the Domino Process: Highly Efficient Synthesis of Fused Tetracyclic Chromenopyran Pyrimidinediones Using Baylis-Hillman Derivatives [J].

Bakthadoss, Manickam ;

Sivakumar, Govindan ;

Kannan, Damodharan .

ORGANIC LETTERS, 2009, 11 (19) :4466-4469

[7] Novel Regio- and Stereoselective Synthesis of Functionalized 3-Spiropyrrolidines and 3-Spiropyrrolizidines Using the Baylis-Hillman Adducts Derived from Nitroolefins [J].

Bakthadoss, Manickam ;

Sivakumar, Nagappan .

SYNLETT, 2009, (06) :1014-1018

[8] Synthesis of some complex pyrano[2,3-b]- and pyrido[2,3-b]quinolines from simple acetanilides via intramofecular domino hetero Diels-Alder reactions of 1-oxa-1,3-butadienes in aqueous medium [J].

Baruah, Biswajita ;

Bhuyan, Pulak J. .

TETRAHEDRON, 2009, 65 (34) :7099-7104

[9] The Baylis-Hillman reaction: a novel concept for creativity in chemistry [J].

Basavaiah, Deevi ;

Veeraraghavaiah, Gorre .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (01) :68-78

[10] 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

← 1 2 3 4 5 6 7 →