Thermolysis of Geminal Diazides: Reagent-Free Synthesis of 3-Hydroxypyridines.
| Autor: | Erhardt H; Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany., Kunz KA; Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany., Kirsch SF; Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany. |
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| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2017 Jan 06; Vol. 19 (1), pp. 178-181. Date of Electronic Publication: 2016 Dec 16. |
| DOI: | 10.1021/acs.orglett.6b03475 |
| Abstrakt: | An operationally simple protocol for the rapid and efficient construction of highly substituted 3-hydroxypyridines is presented. The thermally induced cyclization of easily constructed geminal diazides derived from β-ketoesters having an additional olefin moiety affords the title compounds in yields up to 97% under reagent-free conditions. The new method allows for the synthesis of preparative quantities of material. Additionally, the synthetic utility of the pyridine products for the synthesis of valuable heterocycles is described. |
| Databáze: | MEDLINE |
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