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Abstract
Reaction of phenylpropynehydrazide with dimethylmalonyl chloride furnished the corresponding 4,4‐dimethyl‐1‐(3‐phenylprop‐2‐ynoyl)pyrazolidine‐3,5‐dione, which upon thermolysis underwent a 6‐endo‐dig cyclization to a pyrazolo[5,1‐b][1,3]oxazine. The corresponding reaction of arylpropynehydrazides with monosubstituted malonyl chlorides furnished pyrazolo[5,1‐b][1,3]oxazine‐7‐ones via intermediates that could not be isolated.
The reaction of arylpropynehydrazides with monosubstituted malonyl chlorides leading to pyrazolo[5,1‐b][1,3]oxazines is reported. This method can also be extended to the synthesis of pyrazolidine‐3,5‐dione, which subsequently can be converted by thermolysis into a pyrazolo[5,1‐b][1,3]oxazine.
<!--Unmatched element: w:blockFixed-->| Authors: | Petina, Olga A.; Yakovlev, Igor P.; Geffken, Detlef | |
| Journal: | European Journal of Organic Chemistry | |
| Year: | 2012 | |
| Pages: | n/a | |
| DOI: | 10.1002/ejoc.201200267 | |
| Publication date: | 03-05-2012 |
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