Pyrroles from ketoximes and acetylene. 35. Synthesis of 2-(4-alkylthiophenyl)pyrroles and their 1-vinyl derivatives

✍ Scribed by I. A. Aliev; B. R. Gasanov; N. N. Golovanova; A. I. Mikhaleva

• Publisher: Springer US
• Year: 1987
• Tongue: English
• Weight: 199 KB
• Volume: 23
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00479365

✦ Synopsis

UDC 547.322'572.1'479.07 2-(4-Alkylthiophenyl)-and 2-(4-phenylthiophenyl)pyrroles and their 1-vinyl derivatives were synthesized by the reaction of 4-alkylthio-and 4-phenylthioacetophenone oximes with vinyl chloride in a KOH-DMSO system at 120 and 130~ and at atmospheric pressure.

As we know, several antibiotics belongto the class of arylpyrroles [2-5], and therefore these compounds are becoming more interesting. We therefore developed a method for the synthesis of sulfur-containing 2-(4-alkylthiophenyl)-, 2-(4-phenylthiophenyl)-pyrroles (I-VII) and their 1-vinyl derivatives (VIII-XIII), which may be suitable compounds in a search for biologically active compounds (Tables 1 and2). The method is based on a new variant of the Trofimov reaction [6,7], starting from 4-alkylthio-and 4-phenylthioacetophenone oximes and vinyl chloride, using the superbasic KOH-DMSO catalytic system, taking into account the experience of the preceding investigations described in [8][9][10][11].