Molecules 2010, 15(9), 6106-6126; doi:10.3390/molecules15096106
Article

Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data

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Received: 28 July 2010; in revised form: 27 August 2010 / Accepted: 31 August 2010 / Published: 1 September 2010
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: The synthesis of the title compounds is described. Reaction of 1-substituted 2-pyrazolin-5-ones with 5-chloro-1-phenyl-1H-pyrazole-4-carbonyl chloride or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride, respectively, using calcium hydroxide in refluxing 1,4-dioxane gave the corresponding 4-heteroaroylpyrazol-5-ols, which were cyclized into 1H-pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones by treatment with K2CO3/DMF. The latter were converted into the corresponding thiones upon reaction with Lawesson’s reagent. Detailed NMR spectroscopic investigations (1H, 13C, 15N) of the ring systems and their precursors are presented.
Keywords: pyrazolones; 1H-pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones; cyclization; Lawesson’s reagent; NMR spectroscopy
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MDPI and ACS Style

Datterl, B.; Tröstner, N.; Kucharski, D.; Holzer, W. Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data. Molecules 2010, 15, 6106-6126.

AMA Style

Datterl B, Tröstner N, Kucharski D, Holzer W. Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data. Molecules. 2010; 15(9):6106-6126.

Chicago/Turabian Style

Datterl, Barbara; Tröstner, Nicole; Kucharski, Dorota; Holzer, Wolfgang. 2010. "Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data." Molecules 15, no. 9: 6106-6126.


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