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

被引：12

作者：

Kaniskan, Nevin ^{[2
]}

Elmali, Dilek ^{[2
]}

Civcir, Pervin U. ^{[1
]}

机构：

[1] Ankara Univ, Fac Hlth Sci, TR-06100 Ankara, Turkey

[2] Anadolu Univ, Fac Sci, Dept Chem, Eskisehir, Turkey

来源：

ARKIVOC | 2008年

关键词：

Stetter reaction; Paal-Knorr reaction; imidazole; thiazole; quinoline; pyrrole; thiophene; furan;

D O I：

10.3998/ark.5550190.0009.c03

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：17 / 29

页数：13

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[1] 1H chemical shifts in NMR.: Part 18.: Ring currents and π-electron effects in hetero-aromatics [J].