Patent US4214092A successfully refreshed from Google Patents.
US4214092A
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Rearrangement of acyloxy furans and thiophenes prepared from butenolides
Assignee: Iowa State University Research Foundation Inc
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Filing: 1979-02-21
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Granted: 1980-07-22
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Expires: 1999-02-21
Abstract
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.
Inventors
- 👤 George A. Kraus
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 12:50
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/30; C07D333/32; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/58
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
158 words
A method of preparing rearranged acyloxy furans and thiophenes from butenolides, comprising: reacting a butenolide of the formula: ##STR12## wherein R, R' and R" are selected from the group consisting of hydrogen and non-functionally substituted alkyls, alkenyls, alkynyls and aryls, and W is selected from the group consisting of oxygen and sulfur with an acid and halide acylating agent of the formula: ##STR13## wherein R"' is selected from the same group as R, R' and R" and X is a halide said reaction being conducted in an inert atmosphere and in the presence of a strong organic base and a suitable organic solvent for said base to provide an acylated furan ring containing intermediate; separating said intermediate from other reaction materials; and thereafter reacting said acylated furan ring containing intermediate, in the presence of at least a catalytically effective amount of a lewis acid in an anhydrous solvent to provide a rearranged acyloxy furan or thiophene analog thereof.
Claim 2
Independent Claim
158 words
A method of preparing rearranged acyloxy furans and thiophenes from butenolides, comprising: reacting a butenolide of the formula: ##STR12## wherein R, R' and R" are selected from the group consisting of hydrogen and non-functionally substituted alkyls, alkenyls, alkynyls and aryls, and W is selected from the group consisting of oxygen and sulfur with an acid and halide acylating agent of the formula: ##STR13## wherein R"' is selected from the same group as R, R' and R" and X is a halide said reaction being conducted in an inert atmosphere and in the presence of a strong organic base and a suitable organic solvent for said base to provide an acylated furan ring containing intermediate; separating said intermediate from other reaction materials; and thereafter reacting said acylated furan ring containing intermediate, in the presence of at least a catalytically effective amount of a lewis acid in an anhydrous solvent to provide a rearranged acyloxy furan or thiophene analog thereof.
Claim 3
Dependent Claim
18 words
The process of claim 1 wherein R, R', R" and R"' are C 1 to C 12 substituents.
Claim 4
Dependent Claim
13 words
The process of claim 1 wherein said acid halide is an acid chloride.
Claim 5
Dependent Claim
9 words
The process of claim 1 wherein W is oxygen.
Claim 6
Dependent Claim
15 words
The process of claim 1 wherein said strong organic base is a dialkyl amide base.
Claim 7
Dependent Claim
14 words
The process of claim 1 wherein the process is conducted in an inert solvent.
Claim 8
Dependent Claim
29 words
The process of claim 1 wherein said Lewis acids are selected from the group consisting of boron trifluoride, stannic chloride, aluminum chloride, titanium tetrachloride, zinc chloride and boron trichloride.
Claim 9
Dependent Claim
34 words
The process of claim 1 wherein the amount of said Lewis acid is from about 10% of an equal molar quantity of said acylated furan ring containing intermediate up to an equal molar amount.
Claim 10
Dependent Claim
14 words
The process of claim 1 wherein said anhydrous solvent is a chloro carbon solvent.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-07-22 | 1984-01-21 | 1984-07-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-07-22 | 1988-01-21 | 1988-07-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-07-22 | 1992-01-21 | 1992-07-22 | $7700.00 | Window Closed / Lapsed |