Year: 2018
Type: article
Abstract: We report an approach to the pyrrolo [3,4-b]indole ring system that involves a new synthesis of pyrrolo[3,4b]indol-1(2H)ones, which are known precursors to pyrrolo [3,4-b]indoles.3-Trifluoroacetylindole is prepared from indole and converted into indole carboxamides upon reaction with lithiated amines.Subsequent C-2 bromination followed by a tri-n-butyltin hydride induced 1,5-radical translocation and 5-endo-trig cyclization affords 3,4-dihydropyrrolo [3,4-b]indol-1(2H)-one which upon reduction with DIBAL by the method of Kreher gives pyrrolo [3,4-b]indole.
Source: ARKIVOC
Institution: Dartmouth College
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W2923814435