Some Cycloaddition Reactions of 5,8-Dimethoxynaphtho[2,3-c]furan-4,9-dione

Matthew Piggott, Dieter Wege

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5 Citations (Scopus)

Abstract

Methylation of 5,8-dihydroxynaphtho[2,3-c]furan-4,9-dione (5) gave, in addition to the title ether (7), the fragmentation products 4-hydroxy-1,5,8-trimethoxy-3-methylnaphthalene-2-carbaldehyde (8) and its methyl ether (9). Addition of benzyne to (7) afforded mainly the expected [4+2] cycloadduct (15) and minor amounts of adduct (16), derived by addition of (7) to (15), and adduct (19), derived by a homo- or 1,3-addition of benzyne to (15), followed by decarbonylation. Adducts of (7) with 1,4-dihydro-1,4-epoxynaphthalene and dimethyl acetylenedicarboxylate also were prepared.
Original languageEnglish
Pages (from-to)819-824
JournalAustralian Journal of Chemistry: an international journal for chemical science
Volume51
Issue numberN/A
DOIs
Publication statusPublished - 1998

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Cycloaddition
Methyl Ethers
Methylation
Ether
furan
benzyne
2-methylnaphthalene
acetylenedicarboxylic acid dimethyl ester

Cite this

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title = "Some Cycloaddition Reactions of 5,8-Dimethoxynaphtho[2,3-c]furan-4,9-dione",
abstract = "Methylation of 5,8-dihydroxynaphtho[2,3-c]furan-4,9-dione (5) gave, in addition to the title ether (7), the fragmentation products 4-hydroxy-1,5,8-trimethoxy-3-methylnaphthalene-2-carbaldehyde (8) and its methyl ether (9). Addition of benzyne to (7) afforded mainly the expected [4+2] cycloadduct (15) and minor amounts of adduct (16), derived by addition of (7) to (15), and adduct (19), derived by a homo- or 1,3-addition of benzyne to (15), followed by decarbonylation. Adducts of (7) with 1,4-dihydro-1,4-epoxynaphthalene and dimethyl acetylenedicarboxylate also were prepared.",
author = "Matthew Piggott and Dieter Wege",
year = "1998",
doi = "10.1071/C98031",
language = "English",
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journal = "Australian Journal of Chemistry:an international journal for chemical science",
issn = "0004-9425",
publisher = "CSIRO Publishing",
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TY - JOUR

T1 - Some Cycloaddition Reactions of 5,8-Dimethoxynaphtho[2,3-c]furan-4,9-dione

AU - Piggott, Matthew

AU - Wege, Dieter

PY - 1998

Y1 - 1998

N2 - Methylation of 5,8-dihydroxynaphtho[2,3-c]furan-4,9-dione (5) gave, in addition to the title ether (7), the fragmentation products 4-hydroxy-1,5,8-trimethoxy-3-methylnaphthalene-2-carbaldehyde (8) and its methyl ether (9). Addition of benzyne to (7) afforded mainly the expected [4+2] cycloadduct (15) and minor amounts of adduct (16), derived by addition of (7) to (15), and adduct (19), derived by a homo- or 1,3-addition of benzyne to (15), followed by decarbonylation. Adducts of (7) with 1,4-dihydro-1,4-epoxynaphthalene and dimethyl acetylenedicarboxylate also were prepared.

AB - Methylation of 5,8-dihydroxynaphtho[2,3-c]furan-4,9-dione (5) gave, in addition to the title ether (7), the fragmentation products 4-hydroxy-1,5,8-trimethoxy-3-methylnaphthalene-2-carbaldehyde (8) and its methyl ether (9). Addition of benzyne to (7) afforded mainly the expected [4+2] cycloadduct (15) and minor amounts of adduct (16), derived by addition of (7) to (15), and adduct (19), derived by a homo- or 1,3-addition of benzyne to (15), followed by decarbonylation. Adducts of (7) with 1,4-dihydro-1,4-epoxynaphthalene and dimethyl acetylenedicarboxylate also were prepared.

U2 - 10.1071/C98031

DO - 10.1071/C98031

M3 - Article

VL - 51

SP - 819

EP - 824

JO - Australian Journal of Chemistry:an international journal for chemical science

JF - Australian Journal of Chemistry:an international journal for chemical science

SN - 0004-9425

IS - N/A

ER -