DIRECTED METALATION OF DIARYL SULFONE 2-AMIDES AND 2-O-CARBAMATES - REGIOSPECIFIC GENERAL-ROUTE TO THIOXANTHEN-9-ONE 10,10-DIOXIDES VIA ANIONIC FRIEDEL-CRAFTS AND REMOTE FRIES REARRANGEMENT EQUIVALENTS

被引：29

作者：

BEAULIEU, F ^{[1
]}

SNIECKUS, V ^{[1
]}

机构：

[1] UNIV WATERLOO,GUELPH WATERLOO CTR GRAD WORK CHEM,WATERLOO N2L 3G1,ON,CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 22期

关键词：

D O I：

10.1021/jo00101a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Carboxamido- and 2-O-carbamoyldiaryl sulfones 5, DMG = CONEt(2) and DMG = OCONEt(2), undergo LDA-mediated amide alternate ring migration and cyclization to thioxanthen-9-one 10,10-dioxides 6 and 8, respectively, in a general, synthetically useful reaction.

引用

页码：6508 / 6509

页数：2

共 31 条

[1] REACTIONS OF ORGANOLITHIUM COMPOUNDS WITH SULFONATE ESTERS - NOVEL SULFONE SYNTHESIS [J].

BAARSCHERS, WH .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1976, 54 (19) :3056-3059

[2] STEREOCONTROL AND REGIOCONTROL BY COMPLEX INDUCED PROXIMITY EFFECTS - REACTIONS OF ORGANOLITHIUM COMPOUNDS [J].

BEAK, P ;

MEYERS, AI .

ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (11) :356-363

[3] CYCLIZATION OF DIPHENYL SULFONE-2-CARBOXYLIC A CIDS TO THIAXANTHONE 5,5-DIOXIDES [J].

BENNETT, OF ;

GAUVIN, P .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (12) :4165-&

[4] A SYSTEMATIC INVESTIGATION OF THIOXANTHEN-9-ONES AND ANALOGS AS POTENTIAL ANTITUMOR AGENTS [J].

BLANZ, EJ ;

FRENCH, FA .

JOURNAL OF MEDICINAL CHEMISTRY, 1963, 6 (02) :185-&

[5] METHYL-SUBSTITUTED THIOXANTHONES AND THIOXANTHONE-10,10-DIOXIDES [J].

BRINDLE, ID ;

DOYLE, PP .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (08) :1869-1871

[6] HIGHLY SELECTIVE, KINETICALLY CONTROLLED ENOLATE FORMATION USING LITHIUM DIALKYLAMIDES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE [J].

COREY, EJ ;

GROSS, AW .

TETRAHEDRON LETTERS, 1984, 25 (05) :495-498

[7] MECHANISM OF BASE-CATALYZED DESILYLATIONS OF ARYL-TRIMETHYLSILANES AND HETEROARYLTRIMETHYLSILANES [J].

EFFENBERGER, F ;

SPIEGLER, W .

CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (10) :3872-3899

[8] SULFONYLATION OF ORGANOMETALLIC REAGENTS WITH ARENESULFONYL FLUORIDES - A SIMPLE ONE-STEP SYNTHESIS OF SULFONES [J].

FRYE, LL ;

SULLIVAN, EL ;

CUSACK, KP ;

FUNARO, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :697-701

[9] REMOTE AROMATIC METALATION - AN ANIONIC FRIEDEL-CRAFTS EQUIVALENT FOR THE REGIOSELECTIVE SYNTHESIS OF CONDENSED FLUORENONES FROM BIARYL AND META-TERARYL 2-AMIDES [J].

FU, JM ;

ZHAO, BP ;

SHARP, MJ ;

SNIECKUS, V .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1683-1685

[10] THE METALATION OF SOME SULFUR-CONTAINING ORGANIC COMPOUNDS [J].

GILMAN, H ;

WEBB, FJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (12) :4062-4066

← 1 2 3 4 →