Synthesis of the 6- and 7-Hydroxy-5,8-dioxocarbostyrils

George Pettit; Wayne C. Fleming; Kenneth D. Paull

doi:10.1021/jo01267a033

Synthesis of the 6- and 7-Hydroxy-5,8-dioxocarbostyrils

George Pettit, Wayne C. Fleming, Kenneth D. Paull

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Abstract

Utilizing a condensation reaction between amine I and methyl propiolate to obtain pyridone III followed by reaction with potassium t-butoxide and oxygen in dimethyl sulfoxide, a convenient synthesis of 6-hydroxy-5,8-dioxocarbostyril (V) was achieved. Conversion of 8-hydroxycarbostyril via dinitro (XII) and diamino (XIIIa) intermediates provided the isomeric 7-hydroxy-5,8-dioxocarbostyril (XV). The structures assigned to hydroxyquinones V and XV received support from mass spectral and proton magnetic resonance studies.

Original language	English (US)
Pages (from-to)	1089-1092
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	33
Issue number	3
DOIs	https://doi.org/10.1021/jo01267a033
State	Published - Mar 1 1968

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Organic Chemistry

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title = "Synthesis of the 6- and 7-Hydroxy-5,8-dioxocarbostyrils",

abstract = "Utilizing a condensation reaction between amine I and methyl propiolate to obtain pyridone III followed by reaction with potassium t-butoxide and oxygen in dimethyl sulfoxide, a convenient synthesis of 6-hydroxy-5,8-dioxocarbostyril (V) was achieved. Conversion of 8-hydroxycarbostyril via dinitro (XII) and diamino (XIIIa) intermediates provided the isomeric 7-hydroxy-5,8-dioxocarbostyril (XV). The structures assigned to hydroxyquinones V and XV received support from mass spectral and proton magnetic resonance studies.",

author = "George Pettit and Fleming, {Wayne C.} and Paull, {Kenneth D.}",

year = "1968",

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doi = "10.1021/jo01267a033",

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T1 - Synthesis of the 6- and 7-Hydroxy-5,8-dioxocarbostyrils

AU - Pettit, George

AU - Fleming, Wayne C.

AU - Paull, Kenneth D.

PY - 1968/3/1

Y1 - 1968/3/1

N2 - Utilizing a condensation reaction between amine I and methyl propiolate to obtain pyridone III followed by reaction with potassium t-butoxide and oxygen in dimethyl sulfoxide, a convenient synthesis of 6-hydroxy-5,8-dioxocarbostyril (V) was achieved. Conversion of 8-hydroxycarbostyril via dinitro (XII) and diamino (XIIIa) intermediates provided the isomeric 7-hydroxy-5,8-dioxocarbostyril (XV). The structures assigned to hydroxyquinones V and XV received support from mass spectral and proton magnetic resonance studies.

AB - Utilizing a condensation reaction between amine I and methyl propiolate to obtain pyridone III followed by reaction with potassium t-butoxide and oxygen in dimethyl sulfoxide, a convenient synthesis of 6-hydroxy-5,8-dioxocarbostyril (V) was achieved. Conversion of 8-hydroxycarbostyril via dinitro (XII) and diamino (XIIIa) intermediates provided the isomeric 7-hydroxy-5,8-dioxocarbostyril (XV). The structures assigned to hydroxyquinones V and XV received support from mass spectral and proton magnetic resonance studies.

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JO - Journal of Organic Chemistry

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IS - 3

ER -

Synthesis of the 6- and 7-Hydroxy-5,8-dioxocarbostyrils

Abstract

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