Journal of Heterocyclic Chemistry p. 835 - 841 (1998)
Update date:2022-07-29
Topics:
Lee, Chang Kiu
Yu, Ji Sook
Kim, Sun Hee
2-Heteroaryl 2-heteroaromatic carboxylates were prepared by reactions of 2-heteroaromatic carbonyl chlorides and 2(5H)-furanone, 2(5H)-thiophenone, and 1-methyl-2(5H)-pyrrolone in triethylamine. The 1H nmr spectra of the esters showed that the electronic effect of both heteroaromatic rings did not cause any sizable shift from each other except for 1-methyl-2-pyrrolyl 1-methyl-2-pyrrolecarboxylate (5c). Attempts to cyclize the esters to heteroaryl-fused pyran-2-ones were unsuccessful. The results may be explained by the most stable conformation of the esters in which two heteroatoms are anti along the C-O bond of the ester group.
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