Efficient method for the synthesis of hetarenoindanones based on 3-arylhetarenes and their conversion into hetarenoindenes

被引：48

作者：

Kashulin, IA ^{[1
]}

Nifant'ev, IE ^{[1
]}

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 16期

关键词：

D O I：

10.1021/jo049504w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of hetarenoindanones have been prepared by direct double metalation of the appropriate 3-phenylhetarene with butyllithium in the presence of TMEDA followed by treatment of the resulting dilithium compound with ethyl NiV-dimethylcarbamate. All hetarenoindanones were reduced according to Wolff-Kishner by hydrazine in the presence of KOH to the corresponding hetarenoindenes.

引用

页码：5476 / 5479

页数：4

共 29 条

[1]

BOBERG F, 1983, LIEBIGS ANN CHEM, P1598

[2] THE MECHANISM OF INDOLE FORMATION FROM PHENACYLARYLAMINES .2. THE STABILITY AND REACTIONS OF PHENACYL-NORMAL-ALKYLARYLAMINES [J].

BROWN, F ;

MANN, FG .

JOURNAL OF THE CHEMICAL SOCIETY, 1948, (JUN) :847-858

[3] Synthesis of fluoren-9-ones by the palladium-catalyzed cyclocarbonylation of o-halobiaryls [J].

Campo, MA ;

Larock, RC .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5616-5620

[4] PREPARATION AND REACTIVITY OF 2,2'-DILITHIO-1-PHENYLPYRROLE [J].

CHEESEMAN, GWH ;

GREENBERG, SG .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 166 (02) :139-152

[5]

DALLOCO T, 2002, Patent No. 1226193

[6]

DALLOCO T, 2001, Patent No. 1157046

[7] CYCLODEHYDRATION PROCESSES .1. BENZOFURAN DERIVATIVES FORMED BY CYCLISATION OF OMEGA-ARYLOXYACETOPHENONES [J].

DAVIES, W ;

MIDDLETON, S .

JOURNAL OF THE CHEMICAL SOCIETY, 1958, (FEB) :822-825

[8] Polymerization catalysts with cyclopentadienyl ligands ring-focused to pyrrole and thiophene heterocycles [J].

Ewen, JA ;

Jones, RL ;

Elder, MJ ;

Rheingold, AL ;

Liable-Sands, LM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (41) :10786-10787

[9] Chiral ansa metallocenes with Cp ring-fused to thiophenes and pyrroles: Syntheses, crystal structures, and isotactic polypropylene catalysts [J].

Ewen, JA ;

Elder, MJ ;

Jones, RL ;

Rheingold, AL ;

Liable-Sands, LM ;

Sommer, RD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (20) :4763-4773

[10] N-PHENYLPYRROLE - A KINETIC, THOUGH NOT THERMODYNAMIC PREFERENCE FOR DILITHIATION [J].

FAIGL, F ;

SCHLOSSER, M .

TETRAHEDRON, 1993, 49 (45) :10271-10278

← 1 2 3 →