Reaction of Benzocyclobutenoxides with Nitriles: Synthesis of Hypecumine and Other 3-Substituted Isoquinolines

DOI: 10.1016/0040-4039(94)88462-5

Source and publish data:

Tetrahedron Letters p. 9191 - 9194 (1994)

Update date:2022-08-11

Topics:

Authors:

Fitzgerald, John J.

Michael, Forrest E.

Olofson, R. A.

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Article abstract of DOI:10.1016/0040-4039(94)88462-5

Treatment of benzocyclobuten-2-ols with MeLi affords o-tolualdehyde anions which in the presence of nitriles cyclize to 3-substituted isoquinolines.Examples include the synthesis of the alkaloid hypecumine from the precursors, 14 and 19 (1:1), in 50percen

Full text of DOI:10.1016/0040-4039(94)88462-5

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