Abstract 2‐Vinylindole (1a) and its donor‐ and acceptor‐substituted (E)‐derivatives 1b–e react highly locoselectively with dimethyl 1,2,4,5‐tetrazine‐3,6‐dicarboxylate (3) to form the novel (indol‐2‐yl)‐1,4‐dihydropyridazines 4a and 7 as well as the heterocyclic annellated pyridazines 4b, 5, and 6. The reactions of the structurally related 3‐vinylindoles 2a–e with 3 also gave rise to new indol‐3‐ylpyridazines 8, 9, and 10. The locoselectivities of these Diels‐Alder reactions were controlled mainly by steric effects.
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Pindur et al. (1989) studied this question.
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