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Study on the synthesis of novel 5-substituted 2-[2-(pyridyl)ethenyl]-1,3,4-oxadiazoles and their acid-base interactions.

Kudelko A, Jasiak K, Ejsmont K - Monatsh. Chem. (2014)

Bottom Line: A series of novel 5-substituted 2-[2-(pyridyl)ethenyl]-1,3,4-oxadiazoles were efficiently synthesized by cyclocondensation of the appropriate 3-(pyridyl)acrylohydrazides with triethyl orthoesters in the presence of glacial acetic acid.The products were identified by means of spectroscopic methods and their pK A ionization constants were determined.The influence of substituents on the basicity of the pyridine system has been discussed.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, 44100 Gliwice, Poland.

ABSTRACT

Abstract: A series of novel 5-substituted 2-[2-(pyridyl)ethenyl]-1,3,4-oxadiazoles were efficiently synthesized by cyclocondensation of the appropriate 3-(pyridyl)acrylohydrazides with triethyl orthoesters in the presence of glacial acetic acid. The products were identified by means of spectroscopic methods and their pK A ionization constants were determined. The influence of substituents on the basicity of the pyridine system has been discussed.

No MeSH data available.


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Mentions: The resulting acid hydrazides 5a–5c were heated with an excess of triethyl orthoesters (R = Me, Et, Ph; Scheme 3) in glacial acetic acid, yielding a series of 2-[2-(pyridyl)ethenyl]-1,3,4-oxadiazoles 6a–6i substituted at the 5-position with a phenyl or an alkyl group that have not previously been reported in the literature. The commercially available triethyl orthoesters play the dual role of the synthon introducing the methylene carbon atom and high-boiling solvent.


Study on the synthesis of novel 5-substituted 2-[2-(pyridyl)ethenyl]-1,3,4-oxadiazoles and their acid-base interactions.

Kudelko A, Jasiak K, Ejsmont K - Monatsh. Chem. (2014)

© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4495023&req=5

Mentions: The resulting acid hydrazides 5a–5c were heated with an excess of triethyl orthoesters (R = Me, Et, Ph; Scheme 3) in glacial acetic acid, yielding a series of 2-[2-(pyridyl)ethenyl]-1,3,4-oxadiazoles 6a–6i substituted at the 5-position with a phenyl or an alkyl group that have not previously been reported in the literature. The commercially available triethyl orthoesters play the dual role of the synthon introducing the methylene carbon atom and high-boiling solvent.

Bottom Line: A series of novel 5-substituted 2-[2-(pyridyl)ethenyl]-1,3,4-oxadiazoles were efficiently synthesized by cyclocondensation of the appropriate 3-(pyridyl)acrylohydrazides with triethyl orthoesters in the presence of glacial acetic acid.The products were identified by means of spectroscopic methods and their pK A ionization constants were determined.The influence of substituents on the basicity of the pyridine system has been discussed.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, 44100 Gliwice, Poland.

ABSTRACT

Abstract: A series of novel 5-substituted 2-[2-(pyridyl)ethenyl]-1,3,4-oxadiazoles were efficiently synthesized by cyclocondensation of the appropriate 3-(pyridyl)acrylohydrazides with triethyl orthoesters in the presence of glacial acetic acid. The products were identified by means of spectroscopic methods and their pK A ionization constants were determined. The influence of substituents on the basicity of the pyridine system has been discussed.

No MeSH data available.