Premium
Reaction of 2,2′‐bis( N ‐methylindolyl) with dimethyl acetylenedicarboxylate and thermally‐ and photochemically‐induced cyclizations of the product
Author(s) -
Pindur U.,
Kim Y. S.,
Schollmeyer D.
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320439
Subject(s) - dimethyl acetylenedicarboxylate , chemistry , benzylamine , derivative (finance) , carbazole , medicinal chemistry , amine gas treating , catalysis , isoquinoline , product (mathematics) , organic chemistry , cycloaddition , financial economics , economics , geometry , mathematics
Abstract 2,2′‐Bis( N ‐methylindolyl) 1 reacts with dimethyl acetylenedicarboxylate to furnish the 3‐dimethyl maleoyl‐substituted 2,2′‐bisindolyl 2 . Compound 2 cyclizes under aluminum trichloride catalysis according to a polar process to give a cyclopenta[2,1‐ b :3,4‐ b ′]diindole derivative 4 . Reaction of compound 4 with benzyl‐amine yields the spiro derivative 5 . Photochemically‐induced 1,6‐electrocyclization of compound 2 gives rise to the indolo[2,3‐ a ]carbazole 6 directly, which is readily transformed to the pyrrolo‐annelated carbazole 7 by treatment with benzylamine.