Rearrangement of acyloxy furans and thiophenes prepared from but

Details Rearrangement of acyloxy furans and thiophenes prepared from but Rearrangement of acyloxy furans and thiophenes prepared from but

1979-02-21

1980-07-22

Siegel, Alan

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

2603478, C07D33316, C07D30712

Patent

active

042140927

ABSTRACT:
A method of preparing acyloxy furans and thiophenes from butenolides comprising reacting a pre-selected butenolide with an acylating agent in the presence of a base to provide an acyloxy furan intermediate, which in turn undergoes rearrangement in the presence of Lewis Acids by cleavage of a carbon-oxygen bond, and addition of the cleaved moiety to the furan ring forming a carbon-carbon bond on the ring. The result is a heretofore unknown group of lactone type compounds which are biologically active, in and of themselves, and in addition offer use as versatile synthesis intermediates to achieve, by conventional synthesis methods heretofore unavailable compounds.

REFERENCES:
Olah "Friedel-Crafts & Related Reactions" vol. 1 (1963), pp. 100,101.
Weininger "Contemporary Organic Chemistry" (1972), pp. 404,405.

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