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Decarboxylative Coupling Reaction of 2‐(1 H ‐Indol‐3‐yl)acetic Acids with Indole, Azaindole, Benzimidazole and Indazole Derivatives
Author(s) -
Pillaiyar Thanigaimalai,
Uzair Muhammad,
Ullah Saif,
Schnakenburg Gregor,
Müller Christa E.
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900688
Subject(s) - chemistry , indazole , benzimidazole , indole test , nitrogen atom , acetic acid , decarboxylation , medicinal chemistry , acetic anhydride , stereochemistry , coupling reaction , combinatorial chemistry , organic chemistry , catalysis , ring (chemistry)
3,3′‐Diindolylmethanes (DIMs) are an important class of indole alkaloids that exhibit anti‐inflammatory and anti‐cancer effects. Herein, we report on a new, mild and efficient copper(II)‐promoted decarboxylative coupling reaction of 2‐(1 H ‐indol‐3‐yl)acetic acid derivatives ( 1 a – h ) with a variety of (substituted) indoles ( 2 a – t ) yielding (un)symmetrically substituted DIMs ( 3 a – z , 3 aa – ai ). Reaction of 2‐(1 H ‐indol‐3‐yl)acetic acid ( 1 a ) with 7‐azaindole led to the 3,3′‐connected DIM analog 5 d , while 4‐, 5‐, and 6‐azaindoles and benzimidazole reacted at the N 1‐nitrogen atom. Reaction of 1 a with 1 H ‐indazoles led to a mixture of 1‐ and 2‐substituted indazole derivatives. The new method allows large‐scale synthesis of biologically active DIMs.