Annulation of Primary Amines to Piperazines and Diazaspirocycles Utilizing α-Methyl Benzyl Resin
| Autor: | Calum Macleod, Blanca Martinez-Teipel, William M. Barker, Roland E. Dolle |
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| Rok vydání: | 2005 |
| Předmět: |
Mesylates
Aza Compounds Carbamate Annulation Magnetic Resonance Spectroscopy Primary (chemistry) Molecular Structure Chemistry medicine.medical_treatment General Chemistry Cleavage (embryo) Piperazines Resins Synthetic medicine Combinatorial Chemistry Techniques Organic chemistry Spiro Compounds Carbamates Amines Linker |
| Zdroj: | Journal of Combinatorial Chemistry. 8:132-140 |
| ISSN: | 1520-4774 1520-4766 |
| DOI: | 10.1021/cc050106w |
| Popis: | The microwave-assisted solid-phase synthesis of piperazines, 3,9-diazaspiro[5.5]undecanes and 2,9-diazaspiro[5.5]undecanes is reported. The synthesis relies on the direct annulation of primary amines with resin-bound bismesylates 12, 17, and 22. Critical to the success of this chemistry was the development of α-methyl benzyl carbamate resin linker. This resin permits the cleavage of the heterocycles under mildly acidic conditions, free of contaminating linker-derived N-alkylated byproducts. |
| Databáze: | OpenAIRE |
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