Several pi-excessive heteropolyaromatic compounds, which contain furan and thiophen ring and are possible antifungal agents, have been synthesized in good yields according to two general methods. The first method has been used to prepare compounds possessing thiophens linked by their 2- and 5-positions, such as the ter-aryls , and . Two precursors of these compounds have been obtained either by the Glaser reaction, or using a novel Pd-mediated reaction. The second method,which consists of the Ni-or Pd-catalyzed heteroarylation of heteroarene halides via cross-coupling with heteroaryl Grignard reagents or zinc halides,has been used to prepare the bi-aryls , which contain two heteroaromatic units, and the ter-aryl . Compound has been also prepared starting from 2-(2-thienyl) furan () by selective lithiation, followed by bromination. The 13C NMR signals of and have been assigned on the basis of the literature data and by relaxation measurements. Relaxation data have been also used to obtain qualitative informations on the conformational equilibria of the bi-aryls , and the ter-aryls .

Synthesis and carbon-13 NMR characterization of some pi -excessive heteropolyaromatic compounds

CARPITA, ADRIANO;ROSSI, RENZO;
1985

Abstract

Several pi-excessive heteropolyaromatic compounds, which contain furan and thiophen ring and are possible antifungal agents, have been synthesized in good yields according to two general methods. The first method has been used to prepare compounds possessing thiophens linked by their 2- and 5-positions, such as the ter-aryls , and . Two precursors of these compounds have been obtained either by the Glaser reaction, or using a novel Pd-mediated reaction. The second method,which consists of the Ni-or Pd-catalyzed heteroarylation of heteroarene halides via cross-coupling with heteroaryl Grignard reagents or zinc halides,has been used to prepare the bi-aryls , which contain two heteroaromatic units, and the ter-aryl . Compound has been also prepared starting from 2-(2-thienyl) furan () by selective lithiation, followed by bromination. The 13C NMR signals of and have been assigned on the basis of the literature data and by relaxation measurements. Relaxation data have been also used to obtain qualitative informations on the conformational equilibria of the bi-aryls , and the ter-aryls .
Carpita, Adriano; Rossi, Renzo; Veracini, C. A.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/6416
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