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Base‐Catalyzed Formation of Isoxazoles from Dialkyl Acetylenedicarboxylates and 2‐Nitroacetophenones
Author(s) -
SadeghSamiei Sepehr,
Yavari Issa,
Skoulika Stavroula
Publication year - 2015
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400388
Subject(s) - chemistry , isoxazole , cycloaddition , pyridine , ring (chemistry) , catalysis , medicinal chemistry , sequence (biology) , aryl , base (topology) , combinatorial chemistry , organic chemistry , mathematical analysis , mathematics , biochemistry , alkyl
The reaction of dialkyl acetylenedicarboxylates with 1‐aryl‐2‐nitroethanones in the presence of pyridine leads to dialkyl 5‐aryloyl‐isoxazole‐3,4‐dicarboxylates through a novel mechanism, which involves a [2+2] cycloaddition/ring opening/cyclization sequence.