Molecules 1997, 2(4), 69-79; doi:10.3390/20400069

Synthesis and Reactions of Furo[2,3-b]pyrroles

1,* email, 2, 1 and 3
Received: 27 December 1996; Accepted: 24 January 1997 / Published: 20 April 1997
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: Methyl 6H-furo[2,3-b]pyrrole-5-carboxylate (2a) was prepared by thermolysis of the corresponding methyl 2-azido-3-(3-furyl)propenoate (1). 6-Methyl (2b) and 6-benzyl (2c) derivatives were obtained using phase-transfer catalysis conditions (PTC). The formylation of 2a-2c gave 2-formylated compounds (3a-3c). Compounds 4b, 4c were prepared by reactions of corresponding esters 2b, 2c with hydrazine in refluxing ethanol. By reaction of 3a-3c with hydroxylammonium chloride in acetic anhydride in the presence of pyridine, methyl 2-cyano-6-R1-furo[2,3-b]pyrrole-5-carboxylates (5a-5c) were obtained. The reaction of these compounds with sodium azide and ammonium chloride in dimethylformamide led to methyl 2-(5'-tetrazolyl)-6-R1-furo[2,3-b]pyrrole-5-carboxylates (6a-6c). A series of 5-methoxycarbonyl-6-R1-furo[2,3-b]pyrrole-2-carbaldehyde N,N-dimethylhydrazones (7a-7c) was prepared from methyl 2-formyl-6-R1-furo[2,3-b]pyrrole-5-carboxylates (3a-3c) and unsym-dimethylhydrazine. The correlation of the 13C and 15N chemical shifts with the data of the calculated (AM1) net atomic charges is discussed.
Keywords: Methyl furo[2; 3-b]pyrrole-5-carboxylates; methyl 2-formylfuro[2; 3-b]pyrrole-5-carboxylates; methyl 2-cyanofuro[2; 3-b]pyrrole-5-carboxylates; methyl 2-(5'-tetrazolyl)furo[2; 3-b]pyrrole-5-carboxylates; 5- methoxycarbonylfuro[2; 3-b]pyrrole-2-carbaldehydes N; N-dimethylhydrazones
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MDPI and ACS Style

Krutosiková, A.; Ramsden, C.A.; Dandárová, M.; Lycka, A. Synthesis and Reactions of Furo[2,3-b]pyrroles. Molecules 1997, 2, 69-79.

AMA Style

Krutosiková A, Ramsden CA, Dandárová M, Lycka A. Synthesis and Reactions of Furo[2,3-b]pyrroles. Molecules. 1997; 2(4):69-79.

Chicago/Turabian Style

Krutosiková, A.; Ramsden, C. A.; Dandárová, M.; Lycka, A. 1997. "Synthesis and Reactions of Furo[2,3-b]pyrroles." Molecules 2, no. 4: 69-79.

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