Oxocarbons and related compounds, 31. 3-antipyryl-4-hydroxy-cyclobutenedione (antipyryl-semisquaric acid) ad its derivatives

Antipyrylsemisquaric chloride (9) has been prepared with excellent yield from antipyrylsemiquaric acid (8) and oxalic dichloride in the presence of dimethylformamide. Reaction of 9 with N and S nucleophiles afforded antipyrylsemisquaric acid derivatives, such as amides 12a-t, 14a-e, 15, hydrazides 1...

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Published inZeitschrift für Naturforschung. B, A journal of chemical sciences Vol. 63; no. 1; pp. 55 - 64
Main Authors Schmidt, Arthur H., Kohler, Jochen, Pretsch, Ramona, von Freytag-Loringhoven, Sarah, Wiesert, Peter R.
Format Journal Article
LanguageGerman
Published TUBINGEN Verlag Z Naturforsch 01.01.2008
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
semisquaric acid derivatives
DYES
ALKYL
TOXIN
POLYCARBONYL COMPOUNDS
QUADRATIC ACID
SQUARIC ACID
antipyrylsemisquaric chloride
antipyrine
MONILIFORMIN
ALKENYL
PREPARATIVE CHEMISTRY
cyclobutenediones
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Summary:Antipyrylsemisquaric chloride (9) has been prepared with excellent yield from antipyrylsemiquaric acid (8) and oxalic dichloride in the presence of dimethylformamide. Reaction of 9 with N and S nucleophiles afforded antipyrylsemisquaric acid derivatives, such as amides 12a-t, 14a-e, 15, hydrazides 18a-e, and thioesters 21a-i.
ISSN:0932-0776
DOI:10.1515/znb-2008-0108