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1-phenylpyrazolo[4,35,6]pyrano[3,2-c]pyridine-4(1h)-thione1-phenylpyrazolo(4 ,3 5、6)pyrano[3、2 c]pyridine-4 -thione(1 h)
Molbank 2010, M678; doi:10.3390/M678
OPEN ACCESS
molbank
ISSN 1422-8599
/journal/molbank
Short Note
1-Phenylpyrazolo[4,3:5,6]pyrano[3,2-c]pyridine-4(1H)-thione
Valerie Huemer and Wolfgang Holzer *
Department of Drug and Natural Product Synthesis, Faculty of Life Sciences, University of Vienna,
Althanstrasse 14, A-1090 Vienna, Austria
* Author to whom correspondence should be addressed; E-Mail: wolfgang.holzer@univie.ac.at.
Received: 29 March 2010 / Accepted: 23 April 2010 / Published: 26 April 2010
Abstract: The title compound is prepared by treatment of 1-phenylpyrazolo-
[4,3:5,6]pyrano[3,2-c]pyridin-4(1H)-one with Lawesson’s reagent in refluxing toluene.
1 13 15
Detailed spectroscopic data ( H NMR, C NMR, N NMR, MS) are presented.
Keywords: phenylpyrazolo[4,3:5,6]pyrano[3,2-c]pyridine-4(1H)-thiones; Lawesson’s
reagent; thionation; NMR
Recently, we presented a short and generally applicable synthesis of various fused pyrano
[2,3-c]pyrazol-4(1H)-ones of type D [1–7] via reaction of 1-substituted or 1,3-disubstituted
2-pyrazolin-5-ones (A) with o-halo(hetero)arenecarbonyl chlorides B under the conditions described
by Jensen for the C-4 acylation of pyrazolones (calcium hydroxide, dioxane, reflux) [8]. The formed
4-aroylpyrazol-5-ols C can be smoothly cyclized into the target systems D in alkaline or occasionally
acidic [7] medium (Figure 1). Type D compounds can be recogniz
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