GB953623A - Hydrazones of alpha-bromo-p-methoxy-cinnamaldehyde - Google Patents
Hydrazones of alpha-bromo-p-methoxy-cinnamaldehydeInfo
- Publication number
- GB953623A GB953623A GB1080562A GB1080562A GB953623A GB 953623 A GB953623 A GB 953623A GB 1080562 A GB1080562 A GB 1080562A GB 1080562 A GB1080562 A GB 1080562A GB 953623 A GB953623 A GB 953623A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxy
- amino
- cinnamaldehyde
- oxazolidone
- bromo
- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/28—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention comprises compounds of the formula: <FORM:0953623/C2/1> (wherein R is hydrogen and R1 is amino, or R and R1 together represent a divalent radical of the structure -CH2-CO-NH-, -CH2-CH2-O- <FORM:0953623/C2/2> or <FORM:0953623/C2/3> R comprising the terminal CH2 group of said divalent radical) and their preparation by condensing a -bromo-p-methoxy-cinnamaldehyde with semicarbazide, 1-amino-hydantoin, 3-amino-2-oxazolidone, 5-(o-methoxy-phenoxymethyl)-3-amino-2-oxazolidone or 5-morpholinomethyl-3-amino-2-oxazolidone or an acid-addition salt thereof. The a -bromo-p-methoxy-cinnamaldehyde may in turn be prepared by reacting p-methoxy-benzaldehyde with a vinyl alkyl ether in presence of a Lewis acid, treating the resulting intermediate of the probable structure: <FORM:0953623/C2/4> (wherein Q is the p-methoxyphenyl radical and Q1 is an alkyl radical with a strong acid to give p-methoxy-cinnamaldehyde and brominating this; or by reacting an acetal of p-methoxy-benzaldehyde with a vinyl alkyl ether in presence of a Lewis acid, treating the resulting intermediate of the probable structure: <FORM:0953623/C2/5> with a strong acid and optionally with water to give p-methoxy-cinnamaldehyde and brominating this. Examples are provided, and comparison is made between the bacteriostatic activity of the compounds of the invention and that of compounds of the formula: <FORM:0953623/C2/6> obtained by condensing p-methoxy-benzaldehyde with the appropriate hydrazine. Those obtained from 5-(o-methoxy-phenoxymethyl)-3-amino-2-oxazolidone, 5-morpholinomethyl-3-amino-2-oxazolidone and 1-amino-hydantoin are stated to be new. The bacteriostatic hydrazones of the invention may be combined with carriers in pharmaceutical compositions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH351461 | 1961-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB953623A true GB953623A (en) | 1964-03-25 |
Family
ID=4257617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1080562A Expired GB953623A (en) | 1961-03-24 | 1962-03-21 | Hydrazones of alpha-bromo-p-methoxy-cinnamaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB953623A (en) |
-
1962
- 1962-03-21 GB GB1080562A patent/GB953623A/en not_active Expired
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