By means of an intramolecular Wittig process, 2‐vinylindole ( 2 ) was prepared. The indole 2 functions as a heterocyclic, donor‐activated 1,3‐diene and undergoes [4+2] cycloaddition reactions with dimethyl acetylenedicarboxylate, N ‐phenylmaleimide, and p ‐benzoquinone leading to the novel carbazole dervatives 3 , 4 , 5c , 6 and 7 respectively. The reaction of 2 with acceptor (A)‐Substituted dienophiles ( e.g. ) ACHCH 2 , AC≡(CH) does not yield products that can be isolated.
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Pindur et al. (1988) studied this question.
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