Collect. Czech. Chem. Commun. 1997, 62, 1468-1480

Thieno[3,2-b]benzofuran - Synthesis and Reactions

Petr Váchal, Pavel Pihera and Jiří Svoboda

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic


Thieno[3,2-b]benzofuran was synthesized starting from benzo[b]furan-3(2H)-one or benzo[b]furan-2-carbaldehyde. Electrophilic substitution reactions such as bromination, formylation, acetylation or nitration, take place in position 2. An electron donating group in position 2 directs further electrophilic substitution into positions 3 and 6, whereas compounds with an electron acceptor in position 2 are substituted exclusively in position 6. Metallation with butyllithium took place in position 2. The 1H and 13C NMR signals of the title compound were fully assigned.

Keywords: Fused heterocycles; Thieno[3,2-b]benzofuran; Benzothieno[3,2-b]furan; Electrophilic substitution; Metallation.