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Cycloadditions, XX, Thermally Induced Intramolecular Reactions of 2-Methyl-2,3-butadienamides
Himbert,Gerhard,Schlindwein, Hans-Juergen
, p. 1785 - 1794 (2007/10/02)
The 2-methyl-2,3-butadienamides 4a-m are directly synthesized by the reaction of the corresponding allenic acid chloride 2 with the secondary amines 3.At heating, 4a-j undergo the intramolecular Diels-Alder reaction, by using their ω-standing double bond and the ?-system of the directly bonded phenyl groups or of the "methylenic" bonded arenes of furans.Thereby the tricycles 6a-g (bearing five-membered lactam moieties) and/or the tricycles 7-9 (bearing six-membered lactam moieties) are formed.The influence of the geminal methyl group on the chemoselectivity and on the velocity of the IMDA reactions is investigated.The N-allyl derivatives of 4 (s. 4l and m) form the bicycles 10 by intramolecular -Cycloaddition. Key words: 2-Methyl-2,3-butadienamides, Intramolecular - and -Cycloadditions
