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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 π-system of the directly bonded phenyl groups or of the “methylenic” bonded arenes or furans. Thereby the tricycles 6a—g (bearing five-membered lactam moreties) and/or the tricycles 7-9 (bearing six-membered lactam moreties) are formed. The influence of the geminai methyl group on the chemoselectivity and on the velocity of the IMDA reactions is investigated. The N-allyl derivatives of 4 (s. 41 and m) form the bicycles 10 by intramolecular [2+2]-Cycloaddition.

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Cycloadditionen, XX Thermisch induzierte intramolekulare Reaktionen bei 2-Methyl-2,3-butadienamiden / Cycloadditions, XX Thermally Induced Intramolecular Reactions of 2-Methyl-2,3-butadienamides