Synthesis and reactions of pyrazole-4-carbaldehydes

1-, 3-, and 5-Alkylpyrazoles, as well as linearly bridged bis-pyrazoles, were converted into the corresponding 4-formyl derivatives by Vilsmeier-Haak reaction both under standard conditions and under microwave activation in DMF over a period of 10 min. 1,1'-(Hexane-1,6-diyl)bis(3,5-dimethyl-1H-...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2009-07, Vol.45 (7), p.1040-1044
Main Authors: Rudyakova, E. V, Savosik, V. A, Papernaya, L. K, Albanov, A. I, Evstaf'eva, I. T, Levkovskaya, G. G
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:1-, 3-, and 5-Alkylpyrazoles, as well as linearly bridged bis-pyrazoles, were converted into the corresponding 4-formyl derivatives by Vilsmeier-Haak reaction both under standard conditions and under microwave activation in DMF over a period of 10 min. 1,1'-(Hexane-1,6-diyl)bis(3,5-dimethyl-1H-pyrazole) and 1,1'-(benzene-1,4-diyldimethylene)bis(3,5-dimethyl-1H-pyrazole) gave rise to 4-formyl derivatives at both pyrazole rings. 5-Chloro-1,3-dialkyl-1H-pyrazoles failed to undergo formylation according to Vilsmeier-Haak or under microwave activation. 1,1'-Bridged bis-3,5-dimethyl-1H-pyrazoles reacted with 2-sulfanylethanol on heating in the presence of chloro(trimethyl)silane to give the corresponding bridged bis-4-(1,4,6-oxadithiocan-5-yl)-1H-pyrazoles.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428009070100