A concise route to 4-aminomethylpyrazoles and 4-aminomethylisoxazoles from acetylacetone-derived hexahydropyrimidines under mild conditions
-
Abdullah I. Saleh
,
Kayed A. Abu-Safieh
Abstract
Acetylacetone was successfully used as a precursor of 4-aminomethylpyrazoles and 4-aminomethylisoxazoles in a two step process at ambient temperature. In the first step, acetylacetone was transformed to the corresponding hexahydropyrimidines (1,3-diazinanes) via two consecutive one-pot Mannich aminomethylations. Hexahydropyrimidines were then treated with hydrazine, phenylhydrazine, and hydroxylamine, respectively, to obtain the corresponding 4-aminomethylpyrazoles and 4-aminomethylisoxazoles in good yields. The hexahydropyrimidine ring decomposed providing the title compounds and a reasonable mechanism has been proposed.
References
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Articles in the same Issue
- Perovskite ceramics and recent experimental progress in reactor design for chemical looping combustion application
- Total reflection X-ray fluorescence analysis of fly ash from Bulgarian coal-fired power plants
- Ascorbic acid amperometric sensor using a graphene-wrapped hierarchical TiO2 nanocomposite
- Rapid determination of products of phenol hydrogenation in a supercritical water system using headspace gas chromatography
- Swelling of N-vinylcaprolactam–dodecyl methacrylate gel in {heptane + toluene} mixtures
- Extraction of Cu(II) with Acorga M5640 using hollow fibre liquid membrane
- Heat transfer in a jacketed agitated vessel equipped with multistage impellers
- Seasonal variation in alkaloid composition and antiproliferative activity of Stylophorum lasiocarpum (Oliv.) Fedde
- A polyacrylate prepared using polyurethane surfactants: properties of emulsion and film
- Efficient synthesis of glutaric acid from L-glutamic acid via diazoniation/hydrogenation sequence
- New insights into bromination process: effective preparation of Ambroxol
- A concise route to 4-aminomethylpyrazoles and 4-aminomethylisoxazoles from acetylacetone-derived hexahydropyrimidines under mild conditions
- Assessment of non-standard reaction conditions for asymmetric 1,3-dipolar organocatalytic cycloaddition of nitrone with α,β-unsaturated aldehydes
- β-Cyclodextrin as water-solubility enhancer for butylated hydroxytoluene
- Asymmetric polymerisation of substituted phenylacetylene using chiral Rh(2,5-norbornadiene)(L-proline) catalyst
