Application of organolithium and related reagents in synthesis .18. Synthetic strategies based on aromatic metallation. A conversion of methyl ortho-pyridoylbenzoates into aza-anthra-5,10-quinones

被引：15

作者：

Epsztajn, J

Jozwiak, A

Krysiak, JK

Lucka, D

机构：

[1] Department of Organic Chemistry, Univ. of Łódź, 90-136 Łodz

来源：

TETRAHEDRON | 1996年 / 52卷 / 33期

关键词：

D O I：

10.1016/0040-4020(96)00620-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the aza-anthraquinones (16) and (17) via metallation (LDA / THF) of the pyridine nucleus at the C-3-carbon atom of the methyl ortho-pyridinecarbonyl benzoates (12) and (13), and then the intramolecular cross addition of the generated lithiated species to the carbomethoxy group is described. Copyright (C) 1996 Elsevier Science Ltd

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页码：11025 / 11036

页数：12

相关论文

共 48 条

[1] SYNTHESIS OF BENZ[B]ACRIDINE-6,11,12-TRIONES [J].

ALVAREZ, M ;

AJANA, W ;

LOPEZCALAHORRA, F ;

JOULE, JA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (08) :917-919

[2] FUNGAL METABOLITES .3. QUINONES FROM FUSARIUM SOLANI D2 PURPLE AND STRUCTURE OF (+)-SOLANIOL [J].

ARSENAULT, GP .

TETRAHEDRON, 1968, 24 (13) :4745-+

[3]

ARSENAULT GP, 1965, TETRAHEDRON LETT, V6, P4033

[4] STUDIES IN RELATION TO BIOSYNTHESIS .47. PHOMAZARIN .1. STRUCTURE OF PHOMAZARIN, AN AZA-ANTHRAQUINONE PRODUCED BY PYRENOCHAETA-TERRESTRIS HANSEN [J].

BIRCH, AJ ;

BUTLER, DN ;

EFFENBERGER, R ;

RICKARDS, RW ;

SIMPSON, TJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (03) :807-815

[5]

BOUAMMALI B, 1991, HETEROCYCLES, V32, P915

[6] A REGIOSPECIFIC SYNTHESIS OF 2-AZAANTHRAQUINON-3-ONES VIA A HETERO-DIELS-ALDER REACTION WITH BROMONAPHTHOQUINONES [J].

BOUAMMALI, B ;

PAUTET, F ;

FILLION, H ;

SOUFIAOUI, M .

TETRAHEDRON, 1993, 49 (15) :3125-3130

[7] 1ST SYNTHESIS OF THE BENZO[F]PYRIDO[2',3'/3,4]PYRROLO[2,1-A][2,7]NAPHTHYRIDINE RING-SYSTEM [J].

BRACHER, F .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (01) :157-159

[8]

BRACHER F, 1992, LIEBIGS ANN CHEM, P1205

[9]

CAJORI FA, 1957, J BIOL CHEM, V208, P107

[10] NUCLEOPHILIC ALKENES .3. ADDITION OF 1,1-DIALKOXYETHENES TO 1,4-NAPHTHOQUINONES - 1-2-PROCESS [J].

CAMERON, DW ;

CROSSLEY, MJ ;

FEUTRILL, GI ;

GRIFFITHS, PG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (06) :1335-1352

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