GB1300928A - 0-aza-9-oxafluorenes - Google Patents
0-aza-9-oxafluorenesInfo
- Publication number
- GB1300928A GB1300928A GB23840/69A GB2384069A GB1300928A GB 1300928 A GB1300928 A GB 1300928A GB 23840/69 A GB23840/69 A GB 23840/69A GB 2384069 A GB2384069 A GB 2384069A GB 1300928 A GB1300928 A GB 1300928A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aza
- reaction
- unsubstituted
- phenoxy
- pyridine
- 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
- 238000006243 chemical reaction Methods 0.000 abstract 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- BLUQJCZJRDOPGV-UHFFFAOYSA-N [1]benzofuro[2,3-b]pyridine Chemical class C1=CC=C2C3=CC=CC=C3OC2=N1 BLUQJCZJRDOPGV-UHFFFAOYSA-N 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 3
- CJLLDPUOAPQJJD-UHFFFAOYSA-N 2-phenoxypyridine-3-diazonium Chemical class O(C1=CC=CC=C1)C1=NC=CC=C1[N+]#N CJLLDPUOAPQJJD-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 230000000269 nucleophilic effect Effects 0.000 abstract 2
- 239000012434 nucleophilic reagent Substances 0.000 abstract 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 2
- 238000006303 photolysis reaction Methods 0.000 abstract 2
- 230000015843 photosynthesis, light reaction Effects 0.000 abstract 2
- IAIQTNQPVZZDCR-UHFFFAOYSA-N 1-oxido-[1]benzofuro[2,3-b]pyridin-1-ium Chemical class O1C2=CC=CC=C2C2=C1[N+]([O-])=CC=C2 IAIQTNQPVZZDCR-UHFFFAOYSA-N 0.000 abstract 1
- DLQNTMJEYRCKPO-UHFFFAOYSA-N 2-(2-chlorophenoxy)pyridine Chemical compound ClC1=CC=CC=C1OC1=CC=CC=N1 DLQNTMJEYRCKPO-UHFFFAOYSA-N 0.000 abstract 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 abstract 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 abstract 1
- GITFEFNVRNPOHX-UHFFFAOYSA-N 2-phenoxypyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=CC=C1 GITFEFNVRNPOHX-UHFFFAOYSA-N 0.000 abstract 1
- SUUZDNBBAQOFQR-UHFFFAOYSA-N 3-nitro-2-phenoxypyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1OC1=CC=CC=C1 SUUZDNBBAQOFQR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- 238000007336 electrophilic substitution reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004966 inorganic peroxy acids Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000004967 organic peroxy acids Chemical class 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1300928 1-Aza-9-oxafluorenes GLAXO LABORATORIES Ltd 30 April 1970 [9 May 1969] 23840/69 Heading C2C [Also in Division A5] Novel 1-aza-9-oxafluorenes are prepared (a) by cyclization of a 2-phenoxy-pyridine-3- diazonium salt (which is unsubstituted in an o-position of the phenoxy group) using a catalyst or by photolysis; (b) by photolysis of a 2-(2<SP>1</SP>-halophenoxy)-pyridine or a 2-phenoxypyridine-2<SP>1</SP>-diazonium salt (which is unsubstituted in the 3-position of the pyridine ring); (c) when a nucleophilic residue is present at the 2- and/or 4-position, by reaction of a 2- and/or 4-halo-1-aza-9-oxafluorene with a nucleophilic reagent; (d) when a nucleophilic residue is present at the 2-position, by reaction of a 2- unsubstituted 1-OR<SP>3</SP>-1-aza-9-oxafluorene quaternary salt, wherein R<SP>3</SP> is an aliphatic or araliphatic group, with a nucleophilic reagent; (e) when an oxygen atom is attached to the ring nitrogen atom, by reaction of a 1-aza-9-oxafluorene with an organic or inorganic peracid; (f) when a 6-substituent is present, by direct electrophilic substitution of the corresponding 6-unsubstituted compound; (g) when the starting material for process (d) above is required, by reaction of the corresponding N-oxide with an aliphatic or araliphatic reactive ester; and (h) when a 4-halo substituent is present, by reaction of a 4-unsubstituted 1-aza-9-oxafluorene-1- oxide with a phosphorus oxyhalide. 2 - Phenoxy - pyridine - 3 - diazonium salts (which are unsubstituted in an o-position of the phenoxy group) are prepared by condensation of a phenol having a free o-position with a 2- halo-3-nitropyridine, reduction of the resulting 2-phenoxy-3-nitropyridine and diazotization of the 2 - phenoxy - 3 - aminopyridine so obtained. 2-(o-Chlorophenoxy)-pyridine is prepared by reaction of o-chlorophenol with 2-chloropyridine in the presence of potassium hydroxide.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23840/69A GB1300928A (en) | 1969-05-09 | 1969-05-09 | 0-aza-9-oxafluorenes |
| IE528/70A IE34188B1 (en) | 1969-05-09 | 1970-04-27 | 1-aza-9-oxafluorenes |
| ZA702941*A ZA702941B (en) | 1969-05-09 | 1970-04-30 | Novel heterocyclic compounds having anti-viral activity |
| CH635673A CH541575A (en) | 1969-05-09 | 1970-05-05 | Process for the preparation of new 1-aza-9-oxafluorenes |
| CH671870A CH557375A (en) | 1969-05-09 | 1970-05-05 | PROCESS FOR THE PREPARATION OF NEW 1-AZA-9-OXAFLUORENES AND THEIR USE. |
| DE19702022024 DE2022024A1 (en) | 1969-05-09 | 1970-05-05 | 1-Aza-9-oxafluorenes and processes for their preparation |
| FR7016604A FR2051509B1 (en) | 1969-05-09 | 1970-05-06 | |
| AT412370A AT303717B (en) | 1969-05-09 | 1970-05-06 | Process for the preparation of new 1-aza-9-oxafluorenes and their salts |
| NL7006739A NL7006739A (en) | 1969-05-09 | 1970-05-08 | |
| BE750128D BE750128A (en) | 1969-05-09 | 1970-05-08 | 1-AZA-9-OXAFLUORENES, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATIONS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23840/69A GB1300928A (en) | 1969-05-09 | 1969-05-09 | 0-aza-9-oxafluorenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1300928A true GB1300928A (en) | 1972-12-29 |
Family
ID=10202160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23840/69A Expired GB1300928A (en) | 1969-05-09 | 1969-05-09 | 0-aza-9-oxafluorenes |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT303717B (en) |
| BE (1) | BE750128A (en) |
| CH (2) | CH557375A (en) |
| DE (1) | DE2022024A1 (en) |
| FR (1) | FR2051509B1 (en) |
| GB (1) | GB1300928A (en) |
| IE (1) | IE34188B1 (en) |
| NL (1) | NL7006739A (en) |
| ZA (1) | ZA702941B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018135362A (en) * | 2012-09-20 | 2018-08-30 | ユー・ディー・シー アイルランド リミテッド | Azadibenzofurans for electronic applications |
-
1969
- 1969-05-09 GB GB23840/69A patent/GB1300928A/en not_active Expired
-
1970
- 1970-04-27 IE IE528/70A patent/IE34188B1/en unknown
- 1970-04-30 ZA ZA702941*A patent/ZA702941B/en unknown
- 1970-05-05 CH CH671870A patent/CH557375A/en not_active IP Right Cessation
- 1970-05-05 DE DE19702022024 patent/DE2022024A1/en active Pending
- 1970-05-05 CH CH635673A patent/CH541575A/en not_active IP Right Cessation
- 1970-05-06 AT AT412370A patent/AT303717B/en not_active IP Right Cessation
- 1970-05-06 FR FR7016604A patent/FR2051509B1/fr not_active Expired
- 1970-05-08 NL NL7006739A patent/NL7006739A/xx unknown
- 1970-05-08 BE BE750128D patent/BE750128A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018135362A (en) * | 2012-09-20 | 2018-08-30 | ユー・ディー・シー アイルランド リミテッド | Azadibenzofurans for electronic applications |
| US10249827B2 (en) | 2012-09-20 | 2019-04-02 | Udc Ireland Limited | Azadibenzofurans for electronic applications |
Also Published As
| Publication number | Publication date |
|---|---|
| CH557375A (en) | 1974-12-31 |
| AT303717B (en) | 1972-12-11 |
| ZA702941B (en) | 1971-01-27 |
| NL7006739A (en) | 1970-11-11 |
| FR2051509B1 (en) | 1974-03-22 |
| FR2051509A1 (en) | 1971-04-09 |
| CH541575A (en) | 1973-10-31 |
| IE34188B1 (en) | 1975-03-05 |
| IE34188L (en) | 1970-11-09 |
| BE750128A (en) | 1970-11-09 |
| DE2022024A1 (en) | 1970-11-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |