GB1091618A - Process for the preparation of phenazine derivatives - Google Patents

Process for the preparation of phenazine derivatives

Info

Publication number
GB1091618A
GB1091618A GB3837766A GB3837766A GB1091618A GB 1091618 A GB1091618 A GB 1091618A GB 3837766 A GB3837766 A GB 3837766A GB 3837766 A GB3837766 A GB 3837766A GB 1091618 A GB1091618 A GB 1091618A
Authority
GB
United Kingdom
Prior art keywords
base
oleum
phenazine
suitably
employing
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
Application number
GB3837766A
Inventor
Barrington Cross
Peter John Williams
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to GB3837766A priority Critical patent/GB1091618A/en
Publication of GB1091618A publication Critical patent/GB1091618A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
    • C07D241/52—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/46—Phenazines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Phenazine derivatives of the formula <FORM:1091618/C2/1> and their N-oxides, wherein R represents a halogen atom, or an alkyl, aryl, aralkyl, alkaryl, alkoxy, thioalkyl, alkysulphonyl, arylsulphonyl, hydroxy, cyano, amino, substituted amino or nitro group and m and n each represent 0, 1, 2, 3 or 4, the groups R being the same or different when m + n are greater than 1, are obtained by cyclizing a 2-nitrodiphenylamine of the formula <FORM:1091618/C2/2> by treatment with a base in an organic solvent or with oleum, and optionally converting the product, if an N-oxide, into the corresponding free phenazine base. When effecting the cyclization by employing a base, which may be inorganic, e.g. calcium oxide or an alkali metal hydroxide, or organic, e.g. potassium t-butoxide, the reaction is suitably effected by refluxing a mixture of the diphenylamine and the base in an organic solvent having a boiling point of 130 DEG C. or above, e.g. xylene, cumene, tetralin, naphthalene, chlorobenzene, o-dichlorobenzene or decalin. The reaction employing oleum may suitably be effected at room temperature employing a molar ratio of sulphur trioxide in the oleum to the diphenylamine of at least 5 : 1 and the N-oxide product may be converted to the free phenazine base by heating (suitably at 180 DEG C.) or by reduction with a metallic reducing agent.
GB3837766A 1966-08-26 1966-08-26 Process for the preparation of phenazine derivatives Expired GB1091618A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3837766A GB1091618A (en) 1966-08-26 1966-08-26 Process for the preparation of phenazine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3837766A GB1091618A (en) 1966-08-26 1966-08-26 Process for the preparation of phenazine derivatives

Publications (1)

Publication Number Publication Date
GB1091618A true GB1091618A (en) 1967-11-22

Family

ID=10403085

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3837766A Expired GB1091618A (en) 1966-08-26 1966-08-26 Process for the preparation of phenazine derivatives

Country Status (1)

Country Link
GB (1) GB1091618A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3937707A (en) * 1972-05-01 1976-02-10 Hoffmann-La Roche Inc. 6-substituted 1-phenazinol 5,10-dioxide derivatives
US4055421A (en) * 1974-12-12 1977-10-25 Ricoh Co., Ltd. Sensitizer for photoconductive sensitive material
US4137413A (en) * 1974-12-12 1979-01-30 Ricoh Company, Ltd. 1,3,7-Trinitrophenazine-5-oxide

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3937707A (en) * 1972-05-01 1976-02-10 Hoffmann-La Roche Inc. 6-substituted 1-phenazinol 5,10-dioxide derivatives
US4055421A (en) * 1974-12-12 1977-10-25 Ricoh Co., Ltd. Sensitizer for photoconductive sensitive material
US4137413A (en) * 1974-12-12 1979-01-30 Ricoh Company, Ltd. 1,3,7-Trinitrophenazine-5-oxide

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