GB947127A - 1-benzoxacycloalkanes and methods of preparation - Google Patents
1-benzoxacycloalkanes and methods of preparationInfo
- Publication number
- GB947127A GB947127A GB2193162A GB2193162A GB947127A GB 947127 A GB947127 A GB 947127A GB 2193162 A GB2193162 A GB 2193162A GB 2193162 A GB2193162 A GB 2193162A GB 947127 A GB947127 A GB 947127A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- phenyl
- alkali metal
- benzofuranone
- reflux temperature
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0947127/C2/1> in which Ph is phenyl, n is 1,2 or 3, and R is a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms. Compounds in which R is alkyl are prepared by reacting equimolecular proportions of an alkali metal 3-phenyl-2-benzofuranone and a dihaloalkane of formula X-(CH2)n-X, in which X is chlorine or bromine, in an inert organic solvent at 0 DEG C. to the reflux temperature to obtain the intermediate 3-haloalkyl-3-phenyl-2-benzofuranone which is then reacted with an equivalent amount of alkali metal alkoxide at room temperature to the reflux temperature. For compounds in which R is methyl or ethyl the reaction may take place in one step by refluxing one molecular proportion of each of 3-phenyl-2-benzofuranone and a dihalomethane or dihaloethane with two molecular proportions of an alkali metal alkoxide. Compounds in which R is hydrogen are prepared by reacting a compound selected from <FORM:0947127/C2/2> and <FORM:0947127/C2/3> in which R1 is an alkyl group having from 1 to 4 carbon atoms, with an alkali metal hydroxide in the presence of alcohol or water as solvent, at from about 23 DEG C. to the reflux temperature and then acidifying to precipitate the product. Numerous examples of compounds produced are given. The acid compounds may be further converted to the chloride and reacted with 6-aminopenicillanic acid or an amino alcohol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11560661A | 1961-06-08 | 1961-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB947127A true GB947127A (en) | 1964-01-22 |
Family
ID=22362395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2193162A Expired GB947127A (en) | 1961-06-08 | 1962-06-06 | 1-benzoxacycloalkanes and methods of preparation |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE618528A (en) |
| ES (1) | ES278067A1 (en) |
| GB (1) | GB947127A (en) |
| SE (1) | SE302135B (en) |
-
1962
- 1962-06-05 BE BE618528A patent/BE618528A/en unknown
- 1962-06-06 GB GB2193162A patent/GB947127A/en not_active Expired
- 1962-06-07 ES ES278067A patent/ES278067A1/en not_active Expired
- 1962-06-08 SE SE646562A patent/SE302135B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE618528A (en) | 1962-12-14 |
| SE302135B (en) | 1968-07-08 |
| ES278067A1 (en) | 1963-03-16 |
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