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BY-NC-ND 3.0 license Open Access Published by De Gruyter June 2, 2014

Reactions of Benzofurans, V Formylation and Bromination of 2,3-Diphenylbenzofuran

  • O. H. Hishmat and A. H. Abd-El-Rahman

VILSMEIER-HAACK: formylation of 2,3-diphenylbenzofuran (la) gave the 5,6-diformyl derivative (lb). Huang-Minlon reduction of lb yielded the 5,6-dimethyl derivative (1c). Oxidation of 1c followed by hydrolysis the 2-hydroxy-4,5-dimethylbenzophenone (2b) was obtained.

Condensation of lb with primary amines gave the corresponding Schiff bases (3 a-j).

1a on bromination gave 5-bromo-2,3-diphenylbenzofuran (1 d), which on hydrolysis via oxidation yielded 2-hydroxy-5-bromobenzophenone (2 d). 1d was also obtained by condensation of benzoin and p-bromophenol in presence of sulphuric acid.

Conrad-Limpach reaction of 5-methoxy-6-amino-2,3-diphenylbenzofuran (1e) and ethyl acetoacetate gave 2,3-diphenyl-7-methyl-5-methoxy-9-hydroxy[2,3-f]furoquinoline via the azomethine (4).

Received: 1976-2-11
Published Online: 2014-6-2
Published in Print: 1976-8-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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