A continuation of studies patterning synthetic types after morphine alkaloids has now made possible the introduction of substituents into the critical 1-, 4-, 6- and 9-positions. The present report is concerned with methoxy and hydroxy groups in the 4- and 6-positions, and suitably substituted amino groups in the 1-position. A typical compound is 1-(α-aminoethyl )-4-methoxydibenzofuran hydrochloride (m. p., 268-269°), prepared from the oxime of l-acetyl-4-methoxydibcnzofuran by conventional reactions. So far success has not attended several attempts to bridge the 1- and 9-positions. Where cyclization does take place it goes homonuclearly and not heteronuclearly. It is possible that di-cyclization may proceed easier by first bridging the 1- and 9-positions, and then effecting an oxygen-bridge.
Proceedings of the Iowa Academy of Science
© Copyright 1939 by the Iowa Academy of Science, Inc.
Cook, Thomas H. and Gilman, Henry
"Morphine Alkaloids and Synthetic Dibenzofuran Derivatives,"
Proceedings of the Iowa Academy of Science: Vol. 46:
, Article 48.
Available at: https://scholarworks.uni.edu/pias/vol46/iss1/48