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Efficient palladium‐catalyzed C‐S cross‐coupling reaction of benzo‐2,1,3‐thiadiazole at C‐5‐position: A potential class of AChE inhibitors
Author(s) -
Santos Beatriz F.,
Pereira Caroline F.,
Pinz Mikaela P.,
Oliveira Aline R.,
Brand George,
Katla Ramesh,
Wilhelm Ethel A.,
Luchese Cristiane,
Domingues Nelson L.C.
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5650
Subject(s) - chemistry , catalysis , palladium , thiadiazoles , coupling reaction , acetylcholinesterase , stereochemistry , combinatorial chemistry , thiol , surface modification , medicinal chemistry , enzyme , organic chemistry
Functionalization of 2,1,3‐benzothiadiazole (BTD) with thiols at C‐5 position remains low explored. Moreover, the arylthiol‐substitutions at this position are also unexplored and can not be found by a S N 2 or S N 1 reaction. In this sense, herein we present a new palladium‐catalyzed methodology for a wide variety of unpublished 5‐arylsulfanyl‐benzo‐2,1,3‐thiadiazole derivatives synthesis with moderate to high yields using a low catalytic loading of Pd( L ‐Pro) 2 as low‐coast, and efficient catalyst in low reaction time. Besides, we concluded that the pKa of thiol species has an important role in this catalysis, mainly in the CMD like catalytic cyclo process, which strongly interferes in the reaction yields. Furthermore, arylsulfanyl‐benzo‐2,1,3‐thiadiazoles derivatives have been assessed ( in vitro ) as potential acetylcholinesterase inhibitors.