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1 Polish Journal of Chemistry

1 2000

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Furo[2,3-b]pyrrole Derivatives : Syntheses and Reactions in the Furan and Pyrrole Ring

Sleziak R., Krutosikova A., Cyrański M., Krygowski T.

Polish Journal of Chemistry

2000

Vol. 74, nr 2

207-217

6-Substitued furo[2,3-b] pyrrole-5-carboxylic acids 2b-d as well as their 2-formyl-substitued derivatives 4a-d have been prepared by alkaline hydrolysis of the corresponding esters 1b-d and 3a-d, respectively. A different behaviour of methyl 6H-furo[2,3-b]pyrrole-5-carboxylate 1a in comparison with the 4Hfuro[3,2-b] pyrrole isomer has been discussed in a framework of different acidity of proton of NH group. The hypothesis has been supported by ab initio B3LYP/6-311+G**DTF calculations. The 2-formylated derivatives 3b-d were used for synthesis the propenoid acids 5b-d, the corresponding acid azides 6b-d, new disubstitued ureas 9 or 10, 2-cyano-derivatives 11a-d, which were transfored into the corresponding amidines 12 and substitued arylureas 13 as well as to 5'-tetrazolyl derivative 14. Further methyl 2-triphenylmethyl-6Hfuro[2,3-b]pyrrole-5-carboxylate 15 and its Michael addition product 16 were prepared.