PL404606A1 - Method for the preparation of 1,3,5-triarylbenzene and truxene derivatives - Google Patents

Method for the preparation of 1,3,5-triarylbenzene and truxene derivatives

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Publication number
PL404606A1
PL404606A1 PL404606A PL40460613A PL404606A1 PL 404606 A1 PL404606 A1 PL 404606A1 PL 404606 A PL404606 A PL 404606A PL 40460613 A PL40460613 A PL 40460613A PL 404606 A1 PL404606 A1 PL 404606A1
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PL
Poland
Prior art keywords
group
derivatives
triarylbenzene
general formula
preparation
Prior art date
Application number
PL404606A
Other languages
Polish (pl)
Other versions
PL220792B1 (en
Inventor
Marek Pietraszkiewicz
Michał R. Maciejczyk
Krzysztof P. Górski
Original Assignee
Instytut Chemii Fizycznej Polskiej Akademii Nauk
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.)
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Publication date
Application filed by Instytut Chemii Fizycznej Polskiej Akademii Nauk filed Critical Instytut Chemii Fizycznej Polskiej Akademii Nauk
Priority to PL404606A priority Critical patent/PL220792B1/en
Priority to GB1412023.2A priority patent/GB2520791B/en
Publication of PL404606A1 publication Critical patent/PL404606A1/en
Publication of PL220792B1 publication Critical patent/PL220792B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/36—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing five carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
    • C07C1/2072—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds by condensation
    • C07C1/2074—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds by condensation of only one compound
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/12—Polycyclic non-condensed hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/225—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/29—Saturated compounds containing keto groups bound to rings
    • C07C49/313—Saturated compounds containing keto groups bound to rings polycyclic
    • C07C49/323—Saturated compounds containing keto groups bound to rings polycyclic having keto groups bound to condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
    • C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/025—Sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/50—Pyrenes; Hydrogenated pyrenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Przedmiotem wynalazku jest sposób wytwarzania pochodnych 1,3,5-triarylobenzenu i truksenu, z użyciem aromatycznych ketonów, charakteryzujący się tym, że aromatyczny keton poddaje się reakcji kondensacji aldolowej z użyciem estru alkilowego kwasu ortokrzemowego o ogólnym wzorze Si(OAlkil)4, w którym alkil oznacza grupę CnHn+1, gdzie n = 1 - 10 oraz nieorganicznego lub organicznego kwasu niekarboksylowego jako czynnika kondensującego, w aprotycznym rozpuszczalniku organicznym, z wytworzeniem pochodnych 1,3,5-triarylobenzenu o ogólnym wzorze (1), w którym Ar oznacza fenyl (także podstawiony grupą R), pirenyl, fluorantenyl, trifenylenyl oraz R oznacza wodór, grupę alkilową, chlor, brom, jod lub grupę nitrową, albo z wytworzeniem pochodnych truksenu o ogólnym wzorze (2), w którym R oznacza wodór, grupę alkilową, chlor, brom, jod lub grupę nitrową, stanowiących zmostkowane grupą CH2 pochodne 1,3,5-triarylobenzenów.The subject of the invention is a process for the preparation of 1,3,5-triarylbenzene and truxene derivatives, using aromatic ketones, characterized in that the aromatic ketone is subjected to an aldol condensation reaction using an orthosilicic acid alkyl ester of the general formula Si (OAlkyl) 4, in which alkyl means a CnHn + 1 group, where n = 1-10 and inorganic or organic non-carboxylic acid as a condensing agent, in an aprotic organic solvent, to give 1,3,5-triarylbenzene derivatives of the general formula (1) in which Ar is phenyl (also substituted with an R group), pyrene, fluoranthenyl, triphenylene and R is hydrogen, an alkyl group, chlorine, bromine, iodine or nitro group, or to provide truxene derivatives of the general formula (2) in which R is hydrogen, an alkyl group, chlorine, bromine, iodine or nitro, which are bridged by the CH2 group and are derivatives of 1,3,5-triarylbenzenes.

PL404606A 2013-07-09 2013-07-09 Method for the production of 1,3,5-triarylbenzene and truxene derivatives PL220792B1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PL404606A PL220792B1 (en) 2013-07-09 2013-07-09 Method for the production of 1,3,5-triarylbenzene and truxene derivatives
GB1412023.2A GB2520791B (en) 2013-07-09 2014-07-07 Method of producing derivatives of 1,3,5-triarylbenzene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL404606A PL220792B1 (en) 2013-07-09 2013-07-09 Method for the production of 1,3,5-triarylbenzene and truxene derivatives

Publications (2)

Publication Number Publication Date
PL404606A1 true PL404606A1 (en) 2015-01-19
PL220792B1 PL220792B1 (en) 2016-01-29

Family

ID=51410704

Family Applications (1)

Application Number Title Priority Date Filing Date
PL404606A PL220792B1 (en) 2013-07-09 2013-07-09 Method for the production of 1,3,5-triarylbenzene and truxene derivatives

Country Status (2)

Country Link
GB (1) GB2520791B (en)
PL (1) PL220792B1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106674082A (en) * 2016-12-29 2017-05-17 齐鲁工业大学 Preparation method of star-shaped carbazole
CN116573983B (en) * 2023-05-04 2026-04-07 巢湖学院 A 1,3,5-triarylbenzene compound and its preparation method

Also Published As

Publication number Publication date
GB201412023D0 (en) 2014-08-20
PL220792B1 (en) 2016-01-29
GB2520791A (en) 2015-06-03
GB2520791B (en) 2020-05-13

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