Abstract
Diethyl mesoxalate reacts with 2- and 3-vinylindoles via electrophilic substitution to give new, functionalized and annellated indoles in high regioselectivities. Regio-controlled dimerization processes occur in the reactions of the vinylindoles 5a and 8a. Nitrosobenze reacts with 2- and 3-vinylindoles in a multi-stage sequence including regiospecific tandem hetero-Diels-alder reactions to give the new, 2,3-difunctionalized indoles 11 and 12 which are conformationally stabilized by proton chelation. The heterocumulene chlorosulfonyl isocyanate reacts as a simple electrophile (like diethyl mesoxalate) with 2-vinylindole 5b to give the indole-3-carboxamide 14. In addition, analogous reactions of N -methylindole were also studied and, in most cases, gave comparable reactivity patterns.
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