Abstract
The simple reaction of cyclization of hydrazides of vic-acetylenylbenzoic and acetylenylpyrazole carboxylic acid can lead to four different compounds: five-membered N-aminolactams, six-membered N-aminolactams, six-membered diazinones and diazepinones, but only the first three have been described. In this paper we report the unexpected formation of a bis(pyrazolo[4,3-d][1,2] diazepinone, the structure of which has been established by X-ray crystallography.
| Original language | English |
|---|---|
| Pages (from-to) | 4457-4459 |
| Number of pages | 3 |
| Journal | Tetrahedron Letters |
| Volume | 46 |
| Issue number | 26 |
| DOIs | |
| Publication status | Published - 27 Jun 2005 |
| Externally published | Yes |
Keywords
- Cross-coupling
- Hetarylacetylenes
- Heterocyclization
- Pyrazolopyridines
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Vasilevsky, S. F., Mshvidobadze, E. V., Mamatyuk, V. I., Romanenko, G. V., & Elguero, J. (2005). Unexpected results in the heterocyclization of 5-acetylenylpyrazole-4- carboxylic acid hydrazides under the influence of CuCl: Formation of a diazepinone and dehydrodimerization into the corresponding bis(pyrazolo[4,3-d] [1,2]diazepinone). Tetrahedron Letters, 46(26), 4457-4459. https://doi.org/10.1016/j.tetlet.2005.04.127