ChemInform Abstract: Synthesis and Ring Opening of Alkaloid‐Type Compounds with a Novel Indolo[2,3‐c][2]benzazepine Skeleton.

Solovjova, Joana; Martynaitis, Vytas; Mangelinckx, Sven; Hölzer, W.; Kimpe, Norbert De; Šačkus, Algirdas

doi:10.1002/chin.201016166

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2019

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“…Many of these reactions are complicated by competing N -alkylation of the indole. In spite of this issue, a number of acid promoted [45,46,47], base promoted [48,49,50,51,52,53,54], and transition metal catalyzed [55,56,57,58,59,60,61,62,63,64] transformations have been described to access indolenines from 3-substituted indoles.…”

Section: Introductionmentioning

confidence: 99%

Dialkylation of Indoles with Trichloroacetimidates to Access 3,3-Disubstituted Indolenines

et al. 2019

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2-Substituted indoles may be directly transformed to 3,3-dialkyl indolenines with trichloroacetimidate electrophiles and the Lewis acid TMSOTf. These reactions provide rapid access to complex indolenines which are present in a variety of complex natural products and medicinally relevant small molecule structures. This method provides an alternative to the use of transition metal catalysis. The indolenines are readily transformed into spiroindoline systems which are privileged scaffolds in medicinal chemistry.

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