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Synthesis 2008(13): 2089-2099
DOI: 10.1055/s-2008-1067105
DOI: 10.1055/s-2008-1067105
PAPER
© Georg Thieme Verlag Stuttgart · New York
One-Pot Synthesis Using the Supported Reagent System Na2CO3/SiO2-PPA/SiO2: Synthesis of Benzo[b]thiophenes and Naphthothiophenes
Weitere Informationen
Received
19 March 2008
Publikationsdatum:
21. Mai 2008 (online)
Publikationsverlauf
Publikationsdatum:
21. Mai 2008 (online)
Abstract
A simple and efficient method has been developed for the synthesis of benzo[b]thiophenes and naphtho[2,1-b]thiophenes from arenethiols and α-halo ketones using Na2CO3/SiO2-PPA/SiO2. Reaction of α-halo ketones with arenethiols is promoted by Na2CO3/SiO2 to afford α-sulfanyl ketones, which cyclize in the presence of PPA/SiO2 to give the corresponding thiophene-fused arenes in one-pot. The reaction using α-bromo acetals instead of α-halo ketones also gave the corresponding naphtho[2,1-b]thiophenes via a three-step reaction in one-pot.
Key words
one-pot synthesis - benzothiophenes - naphthothiophenes - supported reagents - acid-base coexistence reaction
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