Application of organolithium and related reagents in synthesis.: Part 21.: Synthetic strategies based on ortho-aromatic metallation.: A concise regiospecific synthesis of arylnaphthalanes as precursors of naphthylisoquinoline alkaloids

被引：5

作者：

Epsztajn, J ^{[1
]}

Józwiak, A ^{[1
]}

Szczesniak, AK ^{[1
]}

机构：

[1] Univ Lodz, Dept Organ Chem, PL-90136 Lodz, Poland

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 16期

关键词：

D O I：

10.1039/a803246g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel procedure is described for synthesising regioselectively substituted biaryls such as 12. It involves converting phthalides 4, via cycloaddition of dimethyl acetylenedicarboxylate to 1-arylisobenzofurans 6, into dimethyl 1-arylnaphthalene-2,3-dicarboxylates 8, which upon hydrolytic decarboxylation give lactones 11 and then esters 12.

引用

页码：2563 / 2567

页数：5

共 14 条

[1] Application of organolithium and related reagents in synthesis.: Part 22.: Synthetic strategies based on ortho-aromatic metallation.: A concise regiospecific conversion of benzoic acids into the 4-pyridyl-2H-phthalazin-1-ones.
Brzezinski, JZ
Epsztajn, J
Bakalarz, AD
Lajszczak, A
Malinowski, Z
SYNTHETIC COMMUNICATIONS, 1999, 29 (03) : 457 - 473
[2] Application of organolithium and related reagents in synthesis.: Part 23:: Synthetic strategies based on ortho-aromatic metallation.: Synthesis of 4b-arylisoindolo[2,1-a]quinoline derivatives
Epsztajn, J
Józwiak, A
Koluda, P
Sadokierska, I
Wilkowska, ID
TETRAHEDRON, 2000, 56 (27) : 4837 - 4844
[3] Application of organolithium and related reagents in synthesis .16. Synthetic strategies based on aromatic metallation. A concise regiospecific conversion of chlorobenzoic acids into their benzylated derivatives
Epsztajn, J
Bieniek, A
Kowalska, JA
MONATSHEFTE FUR CHEMIE, 1996, 127 (6-7): : 701 - 715
[4] Application of organolithium and related reagents in synthesis, part 24. Synthetic strategies based on aromatic metallation. A concise regiospecific conversion of benzoic acids into 2-(1-aryl-2-methoxycarbonylethyl)benzoic acids
Epsztajn, J
Bieniek, A
Kowalska, JA
Kulikiewicz, KK
SYNTHESIS-STUTTGART, 2000, (11): : 1603 - 1607
[5] Application of organolithium compounds in organic synthesis .19. Synthetic strategies based on aromatic metallation. A concise regiospecific synthesis of 3-halogenated picolinic and isonicotinic acids.
Epsztajn, J
Plotka, MW
Grabowska, A
SYNTHETIC COMMUNICATIONS, 1997, 27 (06) : 1075 - 1086
[6] Application of Organolithium and Related Reagents in Synthesis. Part XXVIII [1]. Synthesis Strategies Based on Aromatic Metallation: A Conversion of Benzoic Acids into Arylthiomethyl Aromatic Carboxylic Acids
Adam Bieniek
Jan Epsztajn
Mieczysław W. Płotka
Monatshefte für Chemie / Chemical Monthly, 2003, 134 : 533 - 538
[7] 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
Epsztajn, J
Jozwiak, A
Krysiak, JK
Lucka, D
TETRAHEDRON, 1996, 52 (33) : 11025 - 11036
[8] Application of organolithium and related reagents in synthesis. XXVIII. Synthesis strategies based on aromatic metallation: A conversion of benzoic acids into arylthiomethyl aromatic carboxylic acids
Bieniek, A
Epsztajn, J
Plotka, MW
MONATSHEFTE FUR CHEMIE, 2003, 134 (04): : 533 - 538
[9] APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESIS .14. SYNTHETIC STRATEGIES BASED ON AROMATIC METALATION - A CONCISE REGIOSPECIFIC CONVERSION OF BENZOIC-ACIDS INTO THEIR ORTHO-PYRIDOYL DERIVATIVES
EPSZTAJN, J
JOZWIAK, A
KRYSIAK, JA
TETRAHEDRON, 1994, 50 (09) : 2907 - 2916
[10] APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESIS .13. SYNTHETIC STRATEGIES BASED ON AROMATIC METALATION - A CONCISE REGIOSPECIFIC CONVERSION OF BENZOIC-ACIDS INTO 4-HYDROXY-1-ARYLNAPHTHALENES
EPSZTAJN, J
JOZWIAK, A
SZCZESNIAK, AK
TETRAHEDRON, 1993, 49 (04) : 929 - 938

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