Competitive intramolecular nucleophilic aromatic substitution: A new route to coumarins

C. Alonso; M. M. Olmstead; M. H. Nantz; M. J. Kurth

Competitive intramolecular nucleophilic aromatic substitution: A new route to coumarins

C. Alonso, M. M. Olmstead, M. H. Nantz, M. J. Kurth

Chemistry

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

4-Hydroxy-3-(2′-pyridyl)coumarins (4) (R = 6-Cl, H, 6-NO₂, 8-NO₂) were prepared in moderate to good yields by the intramolecular nucleophilic aromatic substitution reaction of β-ketoesters (I) in refluxing xylenes; evidence for the reversible formation of benzo[c]quinolizinium III from I (X = 4-Cl), with eventual formation of 4 (R = 6-Cl), is also presented.

Original language	English (US)
Pages (from-to)	639-640
Number of pages	2
Journal	Chemical Communications
Issue number	7
State	Published - Apr 7 2001

ASJC Scopus subject areas

Chemistry(all)

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title = "Competitive intramolecular nucleophilic aromatic substitution: A new route to coumarins",

abstract = "4-Hydroxy-3-(2′-pyridyl)coumarins (4) (R = 6-Cl, H, 6-NO2, 8-NO2) were prepared in moderate to good yields by the intramolecular nucleophilic aromatic substitution reaction of β-ketoesters (I) in refluxing xylenes; evidence for the reversible formation of benzo[c]quinolizinium III from I (X = 4-Cl), with eventual formation of 4 (R = 6-Cl), is also presented.",

author = "C. Alonso and Olmstead, {M. M.} and Nantz, {M. H.} and Kurth, {M. J.}",

year = "2001",

month = apr,

day = "7",

language = "English (US)",

pages = "639--640",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Competitive intramolecular nucleophilic aromatic substitution

T2 - A new route to coumarins

AU - Alonso, C.

AU - Olmstead, M. M.

AU - Nantz, M. H.

AU - Kurth, M. J.

PY - 2001/4/7

Y1 - 2001/4/7

N2 - 4-Hydroxy-3-(2′-pyridyl)coumarins (4) (R = 6-Cl, H, 6-NO2, 8-NO2) were prepared in moderate to good yields by the intramolecular nucleophilic aromatic substitution reaction of β-ketoesters (I) in refluxing xylenes; evidence for the reversible formation of benzo[c]quinolizinium III from I (X = 4-Cl), with eventual formation of 4 (R = 6-Cl), is also presented.

AB - 4-Hydroxy-3-(2′-pyridyl)coumarins (4) (R = 6-Cl, H, 6-NO2, 8-NO2) were prepared in moderate to good yields by the intramolecular nucleophilic aromatic substitution reaction of β-ketoesters (I) in refluxing xylenes; evidence for the reversible formation of benzo[c]quinolizinium III from I (X = 4-Cl), with eventual formation of 4 (R = 6-Cl), is also presented.

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M3 - Article

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EP - 640

JO - Chemical Communications

JF - Chemical Communications

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