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Synthesis of 1,1,1-trihalo-4-methoxy-4-[2-heteroaryl]-3-buten-2-ones, the corresponding butan-1,3-dione and azole derivatives

✍ Scribed by Alex F.C Flores; Sergio Brondani; Nilo Zanatta; Adriano Rosa; Marcos A.P Martins

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 162 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02137-8

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✦ Synopsis

The synthesis of 1,1,1-trihalo-4-methoxy-4-[2-thienyl]-3-buten-2-ones, 1,1,1-trihalo-4-methoxy-4-[2-furyl]-3-buten-2-ones and the respective trihalomethyl 1,3-butanone derivatives by trihaloacylation of dimethoxy acetals derived from 2-acetylthiophene and 2-acetylfuran are reported. This is a convenient method to obtain fluorinated and chlorinated 1,3-dielectrophiles from 2-acetylthiophene and 2-acetylfuran. The fluorinated 1,3-dielectrophiles were used to synthesize five new 2-thienyl-and 2-furylazoles. The structure of all products were assigned by 1 HH-and 13 C NMR and mass spectrometry.

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