IE34188B1 - 1-aza-9-oxafluorenes - Google Patents

1-aza-9-oxafluorenes

Info

Publication number
IE34188B1
IE34188B1 IE528/70A IE52870A IE34188B1 IE 34188 B1 IE34188 B1 IE 34188B1 IE 528/70 A IE528/70 A IE 528/70A IE 52870 A IE52870 A IE 52870A IE 34188 B1 IE34188 B1 IE 34188B1
Authority
IE
Ireland
Prior art keywords
aza
reaction
unsubstituted
phenoxy
pyridine
Prior art date
Application number
IE528/70A
Other versions
IE34188L (en
Original Assignee
Glaxo Lab Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Glaxo Lab Ltd filed Critical Glaxo Lab Ltd
Publication of IE34188L publication Critical patent/IE34188L/en
Publication of IE34188B1 publication Critical patent/IE34188B1/en

Links

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. [GB1300928A]
IE528/70A 1969-05-09 1970-04-27 1-aza-9-oxafluorenes IE34188B1 (en)

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 (2)

Publication Number Publication Date
IE34188L IE34188L (en) 1970-11-09
IE34188B1 true IE34188B1 (en) 1975-03-05

Family

ID=10202160

Family Applications (1)

Application Number Title Priority Date Filing Date
IE528/70A IE34188B1 (en) 1969-05-09 1970-04-27 1-aza-9-oxafluorenes

Country Status (9)

Country Link
AT (1) AT303717B (en)
BE (1) BE750128A (en)
CH (2) CH541575A (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)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10249827B2 (en) * 2012-09-20 2019-04-02 Udc Ireland Limited Azadibenzofurans for electronic applications

Also Published As

Publication number Publication date
FR2051509A1 (en) 1971-04-09
IE34188L (en) 1970-11-09
CH557375A (en) 1974-12-31
GB1300928A (en) 1972-12-29
FR2051509B1 (en) 1974-03-22
AT303717B (en) 1972-12-11
BE750128A (en) 1970-11-09
CH541575A (en) 1973-10-31
NL7006739A (en) 1970-11-11
ZA702941B (en) 1971-01-27
DE2022024A1 (en) 1970-11-19

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