Synthesis of quinoxalines or quinolin-8-amines from N-propargyl aniline derivatives employing tin and indium chlorides
| Autor: | Stefan Aichhorn, Markus Himmelsbach, Wolfgang Schöfberger |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
Aniline Compounds
Dose-Response Relationship Drug Molecular Structure Organic Chemistry Tin Compounds Regioselectivity Indium Biochemistry Chloride Structure-Activity Relationship chemistry.chemical_compound Aniline chemistry Main group element Quinoxalines Quinolines medicine Organic chemistry Organic synthesis Lewis acids and bases Hydroamination Physical and Theoretical Chemistry medicine.drug |
| Zdroj: | Organic & Biomolecular Chemistry. 13:9373-9380 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c5ob01532d |
| Popis: | Pyrazino compounds such as quinoxalines are 1,4-diazines with widespread occurrence in nature. Quinolin-8-amines are isomerically related and valuable scaffolds in organic synthesis. Herein, we present intramolecular main group metal Lewis acid catalyzed formal hydroamination as well as hydroarylation methodology using mono-propargylated aromatic ortho-diamines. The annulations can be conducted utilizing equal aerobic conditions with either stannic chloride or indium(iii) chloride and represent primary examples for main group metal catalyzed 6-exo-dig and 6-endo-dig, respectively, cyclizations in such settings. Both types of reactions can also be utilized in a one-pot manner starting from ortho-nitro N-propargyl anilines using stoichiometric amounts SnCl2·2H2O or In powder. Mechanistic considerations are presented regarding the substituent-depending regioselectivity. |
| Databáze: | OpenAIRE |
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