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First Electrophilic Substitutions of 3‐Substituted Indoles with Diethoxycarbenium Tetrafluoroborate: Functionalized Indole Derivatives
Author(s) -
Pindur Ulf,
Flo Camran
Publication year - 1990
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19903230205
Subject(s) - tetrafluoroborate , indole test , chemistry , electrophile , electrophilic substitution , tris , medicinal chemistry , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , ionic liquid , biochemistry
The indoles 2a‐2c react with diethoxycarbenium tetrafluoroborate ( 1 ) to furnish the indolecarbaldehydes 3a‐3d . In the thermodynamically controlled reaction of 3‐methylindole ( 2a ) with 1 the tris(indolyl)methane 4 and diskatole ( 5 ), are formed in addition. The limitations of these reactions are discussed and evidence is presented for a C‐3‐ ipso ‐attack and a Wagner‐Meerwein rearrangement, respectively, leading to the formation of 3b or 3d .