- A Journey through Hemetsberger–Knittel, Leimgruber–Batcho and Bartoli Reactions: Access to Several Hydroxy 5- and 6-Azaindoles
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The preparation of various 5- and 6-azaindoles, heterocyclic structures that are frequently part of molecules in clinical development, and their monohydroxy analogues were described. Different strategies, relying on the de novo pyrrole ring formation, were investigated and, thanks to Hemetsberger–Knittel, Bartoli and Leimgruber–Batcho approaches, 4- and 7-monohydroxy 5- and 6-azaindoles were obtained. The crucial introduction of the oxygen atom was carried out from halogen derivatives, using nucleophilic substitution reactions under basic conditions with or without a copper catalyst. Some preliminary oxidation reactions have shown that it was yet not possible to synthesize the azaquinone indole structure from monohydroxy azaindole, using molecular oxygen in the presence of salcomine as a catalyst.
- Auberger, Ludovic,Barret, Roland,Bouchez, Grégoire,Hallé, Fran?ois,Lomberget, Thierry,Mahiout, Zahia,Radix, Sylvie,Teissonnière, Amélie
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- Nitrogen-containing heterocyclic compound as well as preparation method, pharmaceutical composition and application thereof
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The invention provides a nitrogen-containing heterocyclic compound as well as a preparation method, a pharmaceutical composition and application thereof, and particularly provides a compound as shownin a formula I which is described in the specification,
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Paragraph 0333; 0341-0345
(2020/05/02)
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- The Hemetsberger-Knittel synthesis of substituted 5-, 6-, and 7-azaindoles
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A series of substituted 5-, 6-, and 7-azaindoles were prepared via the Hemetsberger-Knittel reaction. In general, better yields were obtained at higher temperatures and shorter reaction times than required for the formation of the analogous indoles, and in some cases, only decomposition occurred below a minimum temperature. The resulting templates offer up to five sites for subsequent functionalization to allow a wide range of chemical diversity. Georg Thieme Verlag Stuttgart.
- Roy, Patrick J.,Dufresne, Claude,Lachance, Nicolas,Leclerc, Jean-Philippe,Boisvert, Michel,Wang, Zhaoyin,Leblanc, Yves
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p. 2751 - 2757
(2007/10/03)
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