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Regioselectivity in electrophilic substitution of 5-aminoindoles and 5-aminoindolines: synthesis of pyrrolo[3,2-e]indoles and isomeric pyrrolo[2,3-f]indoles

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
32
Issue
38
Identifiers
DOI: 10.1016/s0040-4039(00)93421-x

Abstract

Abstract An FMO Theory prediction that 5-aminoindoles, 5, should react with electrophiles preferentially at C 4 rather than at C 6 whereas N 1-acyl-5-aminoindolines, 6, should react preferentially at C 6 rather than C 4 is borne out experimentally by the synthesis of a pyrrolo[3,2-e]indole from 5 and pyrrolo[2,3-f]indoles from 6.

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