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ChemInform Abstract: 2-Aminobuta-1,3-dienes as Annulation Reagents for 4-Quinolones and Benzothiopyran-4-ones: An Attractive Route for the Highly Diastereoselective Synthesis of Acridine- and Thioxanthene-Derivatives.

✍ Scribed by U. BEIFUSS; M. TARASCHEWSKI


Publisher
John Wiley and Sons
Year
2010
Weight
39 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis


2-Aminobuta-1,3-dienes as Annulation Reagents for 4-Quinolones and Benzothiopyran-4-ones: An Attractive Route for the Highly Diastereoselective Synthesis of Acridine-and Thioxanthene-Derivatives.

-The enamines (III) serve as nucleophiles for the regioselective 1,2-addition to quinolinium triflates and benzothiopyrylium triflates. No reaction is observed if the quinolinium triflates are reacted with the butadienes (VI). However, the annulation can be achieved if the quinolones (I) are reacted with (VI) in the presence of BF 3 •Et 2 O as a Lewis acid.