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Intermolecular diels-alder reactions of n-acyl-n-alkyl(aryl)-1-amino-1,3-dienes

✍ Scribed by Wolfgang Oppolzer; Lothar Bieber; Eric Francotte


Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
208 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis


Intermolecular Diels-Alder additions of the readily available dienamides 3 to various dienophiles proceeded in a regio-and stereoselective manner, allowing the preparatTon of complex anilides (z), cyclohexenyl amides (2, 8) and bridged heterocycles (13).


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Recent work in this laboratory has shown N-acylamino-1,3-butadienes (4) to be valuable components for intramolecular Diels-Alder reactions. Thus, heating the dienes 4, R2,R3 = 3-or 4-alkenyl, readily provides complex hydrogenated indolines and quinolines 2) as illustrated by the stereocontrolled