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Chemistry of aminophenols. Part 3: First synthesis of nitrobenzo[b]furans via a coupling–cyclization approach

✍ Scribed by Wei-Min Dai; Kwong Wah Lai


Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
186 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


The first synthesis of 4-, 5-, and 6-nitrobenzo[b]furans has been achieved via the Sonogashira cross-coupling reaction of 2-iodonitrophenol acetates prepared from commercially available and inexpensive 2-aminonitrophenols. The obtained 2alkynylnitrophenol acetates were subjected to a KO t Bu-promoted cyclization at room temperature to form nitrobenzo[b]furans. Examples of the synthesis of other substituted benzo[b]furans and the one-pot coupling-cyclization are given.


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