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GB796951A - A new method for the synthesis of phenanthridines - Google Patents

A new method for the synthesis of phenanthridines

Info

Publication number
GB796951A
GB796951A GB3620353A GB3620353A GB796951A GB 796951 A GB796951 A GB 796951A GB 3620353 A GB3620353 A GB 3620353A GB 3620353 A GB3620353 A GB 3620353A GB 796951 A GB796951 A GB 796951A
Authority
GB
United Kingdom
Prior art keywords
chloride
diphenyl
aluminium
phenanthridine
give
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
GB3620353A
Inventor
Wallace Frank Short
Charles Alan Bartram
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.)
Boots Pure Drug Co Ltd
Original Assignee
Boots Pure Drug Co 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 Boots Pure Drug Co Ltd filed Critical Boots Pure Drug Co Ltd
Priority to GB3620353A priority Critical patent/GB796951A/en
Publication of GB796951A publication Critical patent/GB796951A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/10—Aza-phenanthrenes
    • C07D221/12—Phenanthridines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

Phenanthridines of the formula <FORM:0796951/IV (b)/1> and diazapyrenes of the formula <FORM:0796951/IV (b)/2> in which R is aryl, and the nuclei X and Y may be unsubstituted or may carry as substituents one or more groups which are inert under the conditions of the reaction, are made by reacting a 2-aminodiphenyl derivative of the formula <FORM:0796951/IV (b)/3> with stannic chloride, phosphorus pentachloride, zinc chloride, aluminium chloride, the eutectic mixture of aluminium and sodium chlorides, or with phosphorus oxychloride, provided that the last-named is used in conjunction with a nitroaromatic solvent. Solvents specified are nitrobenzene, tetrachlorethane, polychlorinated benzene. In examples: (1) 2-benzylideneaminodiphenyl is heated in various solvents with stannic chloride, zinc chloride, an aluminium chloride-sodium chloride mixture or aluminium chloride alone, or with phosphorus oxychloride and nitrobenzene to give 9-phenylphenanthridine, (2) 2 - benzylideneamino - 4,41 - dinitrodiphenyl is heated with phosphorus pentachloride to give 2,7-dinitro-9-phenyl-phenanthridine, (3) 2-(o - chlorbenzylideneamino)-diphenyl, 2 - (p - methoxybenzylideneamino)-diphenyl, 2,41 - dibenzylideneaminodiphenyl, and 2,21 - dibenzylideneaminodiphenyl are each heated with stannic chloride to give 9-(o-chlorphenyl) - phenanthridine, 9 - (p - methoxyphenyl) - phenanthridine, 7 - amino - 9 - phenylphenanthridine, and 2,7 - diphenyl - 1,6 - diazopyrene. The above-mentioned benzylideneamino diphenyl derivatives are obtained by reaction of the corresponding benzaldehyde and aminodiphenyl derivatives.
GB3620353A 1953-12-30 1953-12-30 A new method for the synthesis of phenanthridines Expired GB796951A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3620353A GB796951A (en) 1953-12-30 1953-12-30 A new method for the synthesis of phenanthridines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3620353A GB796951A (en) 1953-12-30 1953-12-30 A new method for the synthesis of phenanthridines

Publications (1)

Publication Number Publication Date
GB796951A true GB796951A (en) 1958-06-25

Family

ID=10385921

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3620353A Expired GB796951A (en) 1953-12-30 1953-12-30 A new method for the synthesis of phenanthridines

Country Status (1)

Country Link
GB (1) GB796951A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010094736A1 (en) * 2009-02-19 2010-08-26 Basf Se Method for producing 2-aminobiphenylene
US8637707B2 (en) 2008-07-03 2014-01-28 Basf Se Method for producing aminobiphenylene

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8637707B2 (en) 2008-07-03 2014-01-28 Basf Se Method for producing aminobiphenylene
WO2010094736A1 (en) * 2009-02-19 2010-08-26 Basf Se Method for producing 2-aminobiphenylene
CN102325747A (en) * 2009-02-19 2012-01-18 巴斯夫欧洲公司 Method for producing 2-aminobiphenylene
US8492558B2 (en) 2009-02-19 2013-07-23 Basf Se Method for producing 2-aminobiphenylene
CN102325747B (en) * 2009-02-19 2015-01-07 巴斯夫欧洲公司 Method for producing 2-aminobiphenylene

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