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

被引：47

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
BROWN, F
MANN, FG
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1948, (JUN): : 847 - 858
[3] Synthesis of fluoren-9-ones by the palladium-catalyzed cyclocarbonylation of o-halobiaryls
Campo, MA
Larock, RC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) : 5616 - 5620
[4] PREPARATION AND REACTIVITY OF 2,2'-DILITHIO-1-PHENYLPYRROLE
CHEESEMAN, GWH
GREENBERG, SG
[J]. 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
DAVIES, W
MIDDLETON, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1958, (FEB): : 822 - 825
[8] Polymerization catalysts with cyclopentadienyl ligands ring-focused to pyrrole and thiophene heterocycles
Ewen, JA
Jones, RL
Elder, MJ
Rheingold, AL
Liable-Sands, LM
[J]. 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
Ewen, JA
Elder, MJ
Jones, RL
Rheingold, AL
Liable-Sands, LM
Sommer, RD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (20) : 4763 - 4773
[10] N-PHENYLPYRROLE - A KINETIC, THOUGH NOT THERMODYNAMIC PREFERENCE FOR DILITHIATION
FAIGL, F
SCHLOSSER, M
[J]. TETRAHEDRON, 1993, 49 (45) : 10271 - 10278

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