Synthesis and characterization of novel heterosubstituted pyrroles, thiophenes, and furans

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KANIŞKAN N., ELMALI D., ÜNAL CİVCİR P.

ARKIVOC, vol.2008, pp.17-29, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 2008
  • Publication Date: 2008
  • Doi Number: 10.3998/ark.5550190.0009.c03
  • Journal Name: ARKIVOC
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.17-29
  • Keywords: Stetter reaction, Paal-Knorr reaction, imidazole, thiazole, quinoline, pyrrole, thiophene, furan, ACTIVATED DOUBLE-BONDS, EXTENDED HETEROCYCLIC-SYSTEMS, CONDUCTING POLYMERS, ALDEHYDES, PYRIDINE, DERIVATIVES, PROTOPHANES, CONVENIENT, ARYLATION, GAMMA
  • Anadolu University Affiliated: Yes

Abstract

Sixteen new compounds, including novel five-membered heterocyclic systems (pyrrole, thiophene, or furan) linked to imidazole, thiazole, or quinoline rings are reported. The intermediate 1,4-diketones were synthesized via the Stetter reaction in the presence of thiazolium salt as a catalyst. Cyclization reactions of the 1,4-dicarbonyl compounds with polyphosphoric acid, ammonium acetate or Lawesson's reagent by the Paal-Knorr synthesis, afforded unknown 2,5-disubstituted furan, pyrrole, or thiophene compounds in moderate yields, respectively. The structures of the synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR, and elemental analysis.