Tandem [4+2]/[2+2] Cycloaddition Reactions Involving Indene or Benzofurans and Arynes

被引：55

作者：

Bhojgude, Sachin Suresh ^{[1
]}

Thangaraj, Manikandan ^{[1
]}

Suresh, Eringathodi ^{[2
,3
]}

Biju, Akkattu T. ^{[1
]}

机构：

[1] CSIR Natl Chem Lab CSIR NCL, Div Organ Chem, Pune 411008, Maharashtra, India

[2] Analyt Dept, Bhavnagar 364002, Gujarat, India

[3] Centralized Instrument Facil CSIR CSMCRI, Bhavnagar 364002, Gujarat, India

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 13期

关键词：

DIELS-ALDER REACTION; KETENE SILYL ACETAL; CHEMICAL CARCINOGENESIS; ORGANIC-SYNTHESIS; PHENYL LITHIUM; BENZYNE; CHEMISTRY; BENZO<B>FLUORANTHENE; METABOLITES; DERIVATIVES;

D O I：

10.1021/ol501579d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of arynes with indene/benzofurans has been developed. The arynes were generated from 2(trimethylsilyl)aryl triflates by the fluoride-induced 1,2-elimination react with indene or various benzofurans proceeding via a cascade reaction involving the Diels-Alder reaction and a [2 + 2] cycloaddition reaction. The tandem process afforded functionalized dihydrobenzocyclobutaphenanthrenes in moderate to good yields. Moreover, the method has been utilized for the one-pot synthesis of benzo[b]fluoranthene.

引用

页码：3576 / 3579

页数：4

共 42 条

[1] A STUDY OF CHEMICAL CARCINOGENESIS .84. SYNTHESIS AND FLUORESCENCE-SPECTRA OF STRUCTURAL ANALOGS OF POTENTIAL BENZO[B]FLUORANTHENE-DNA ADDUCTS [J].

AMIN, S ;

BALANIKAS, G ;

HUIE, K ;

HUSSAIN, N ;

GEDDIE, JE ;

HECHT, SS .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) :4642-4646

[2] A STUDY OF CHEMICAL CARCINOGENESIS .93. SYNTHESIS OF POTENTIAL PHENOLIC METABOLITES OF BENZO[B]FLUORANTHENE [J].

AMIN, S ;

HUIE, K ;

HUSSAIN, N ;

BALANIKAS, G ;

CARMELLA, SG ;

HECHT, SS .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (08) :1206-1211

[3] A STUDY OF CHEMICAL CARCINOGENESIS .57. SYNTHESIS AND MUTAGENICITY OF DIHYDRODIOL METABOLITES OF BENZO[B]FLUORANTHENE [J].

AMIN, S ;

HUSSAIN, N ;

BRIELMANN, H ;

HECHT, SS .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (06) :1091-1095

[4] THE ADDITION OF BENZYNE TO BENZOFURAN - A READY ROUTE TO BENZ[E]ACEPHENANTHRYLENE [J].

ANTHONY, IJ ;

WEGE, D .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (06) :1283-1292

[5] Efficient Synthesis of 9-Aryldihydrophenanthrenes by a Cascade Reaction Involving Arynes and Styrenes [J].

Bhojgude, Sachin Suresh ;

Bhunia, Anup ;

Gonnade, Rajesh G. ;

Biju, Aldcattu T. .

ORGANIC LETTERS, 2014, 16 (03) :676-679

[6] A Practical and General Diels-Alder Reaction of Pentafulvenes with Arynes [J].

Bhojgude, Sachin Suresh ;

Kaicharla, Trinadh ;

Bhunia, Anup ;

Biju, Akkattu T. .

ORGANIC LETTERS, 2012, 14 (16) :4098-4101

[7] Arynes in Transition-Metal-Free Multicomponent Coupling Reactions [J].

Bhojgude, Sachin Suresh ;

Biju, Akkattu T. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (07) :1520-1522

[8] Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes [J].

Bhunia, Anup ;

Yetra, Santhivardhana Reddy ;

Biju, Akkattu T. .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) :3140-3152

[9] Indole-derived arynes and their diels-alder reactivity with Furans [J].

Buszek, Keith R. ;

Luo, Diheng ;

Kondrashov, Mikhail ;

Brown, Nell ;

VanderVelde, David .

ORGANIC LETTERS, 2007, 9 (21) :4135-4137

[10]

Chen Y, 2009, MODERN ARYLATION METHODS, P401, DOI 10.1002/9783527627325.ch12

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