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GB1189514A - New Cyclic Ketones - Google Patents

New Cyclic Ketones

Info

Publication number
GB1189514A
GB1189514A GB33740/67A GB3374067A GB1189514A GB 1189514 A GB1189514 A GB 1189514A GB 33740/67 A GB33740/67 A GB 33740/67A GB 3374067 A GB3374067 A GB 3374067A GB 1189514 A GB1189514 A GB 1189514A
Authority
GB
United Kingdom
Prior art keywords
radical
cycloalkyl
alkyl
ketones
aralkyl
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
GB33740/67A
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.)
Sandoz AG
Original Assignee
Sandoz AG
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 Sandoz AG filed Critical Sandoz AG
Publication of GB1189514A publication Critical patent/GB1189514A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone
    • 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
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)

Abstract

1,189,514. Ketones. SANDOZ Ltd. 21 July, 1967 [22 July, 1966], No. 33740/67. Heading C2C. [Also in Division C3] The invention comprises novel ketones of the general formula wherein R 1 is C1, Br, CN, R 3 , -OR 3 , -O-aryl, -CO-OR 3 , -O-COR 3 , -CO-alkyl, w-halogenoalkyl-CO-, -CO-aralkyl, -CO- cycloalkyl, -SO 3 H, or an optionally substituted carboxylic acid amide or sulphonic acid amide radical, R 2 is a carbocyclic or heterocyclic aromatic radical which may contain one or more substituents selected from Cl, Br, alkyl, cycloalkyl, -OR 3 , -COO-R 3 and -CO-N(R 3 )R 4 , X is -O-, -S-, -N(R 3 )-, -C(R 3 )(R 4 )-, -CH=CN- or -C(OR 3 ) = C(OR 4 )-, R 3 is H, alkyl, alkenyl, aralkyl, or cycloalkyl, R 4 is H, alkyl, aralkyl or cycloalkyl and each of n or m is 1 or 2, wherein at least one -OR 3 radical must be present. The compounds of Formula I, except wherein R 3 is alkenyl and R 1 is -SO 3 H or w-halogenoalkyl-CO- are prepared by reacting a compound of the general formula wherein R 5 =R 1 and -COOR 4 , -O-CO-R 4 but not -COOR 3 or -O-CO-R 3 , with a compound of the formula V-R 2 , wherein U and V represent H and a -CO- halogen radical or vice versa, and at least one of the starting materials contains an -OR 3 radical. The reaction is performed by Friedel-Crafts method, preferably using AlCl 3 . Examples include the preparation of hydroxy benzoyldibenzofurans, -carbazoles, -fluorenes and -phenanthreries e.g. dibenzofuran is reacted with 2-methoxybenzoyl chloride to yield 3- (21-hydroxybenzoyl)-dibenzofuran. Ketones having increased solubility in organic solvents are obtained by introducing halogen atoms into the molecule as in Example 39 where 3 - (2<SP>1 </SP>- hydroxy - 3<SP>1 </SP>- methylbenzoyl) - 9 - ethylcarbazole is treated with SO 2 Cl 2 to givethe 6-chloroderivative. The methoxy-, methyl- and chloro-substituted benzoic acid halides, used in the preparation, especially the acid chlorides are obtained from the corresponding carboxylic acids e.g. with SOCl 2 or a phosphorus chloride.
GB33740/67A 1966-07-22 1967-07-21 New Cyclic Ketones Expired GB1189514A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1062966A CH491848A (en) 1966-07-22 1966-07-22 Process for the preparation of new aryl ketones

Publications (1)

Publication Number Publication Date
GB1189514A true GB1189514A (en) 1970-04-29

Family

ID=4365207

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33740/67A Expired GB1189514A (en) 1966-07-22 1967-07-21 New Cyclic Ketones

Country Status (5)

Country Link
BE (1) BE701017A (en)
CH (1) CH491848A (en)
DE (1) DE1695743A1 (en)
GB (1) GB1189514A (en)
NL (1) NL6709076A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102924710A (en) * 2012-10-23 2013-02-13 中国科学院长春应用化学研究所 Polyaryletherketone resin with carbazole ring in main chain and preparation method thereof
CN102924366A (en) * 2012-10-23 2013-02-13 中国科学院长春应用化学研究所 Carbazole ketone intermediate containing multi-functional group structure and preparation method for carbazole ketone intermediate
WO2018049976A1 (en) * 2016-09-13 2018-03-22 常州强力先端电子材料有限公司 Fluorene photoinitiator, preparation method therefor, photocurable composition having same, and use of same in photocuring field
CN109265418A (en) * 2018-09-19 2019-01-25 华南理工大学 A kind of room temperature phosphorimetry material based on dibenzofurans and its preparation method and application containing carbonyl
US11054743B2 (en) 2015-12-15 2021-07-06 Changzhou Tronly Advanced Electronic Materials Co., Ltd. Fluorene polyfunctional photoinitiator and preparation and use thereof, and photosensitive resin composition containing fluorene photoinitiator and use thereof
US11118065B2 (en) 2017-02-17 2021-09-14 Changzhou Tronly Advanced Electronic Materials Co., Ltd. Fluorenylaminoketone photoinitiator, preparation method thereof, and UV photocurable composition containing same

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102924710A (en) * 2012-10-23 2013-02-13 中国科学院长春应用化学研究所 Polyaryletherketone resin with carbazole ring in main chain and preparation method thereof
CN102924366A (en) * 2012-10-23 2013-02-13 中国科学院长春应用化学研究所 Carbazole ketone intermediate containing multi-functional group structure and preparation method for carbazole ketone intermediate
US11054743B2 (en) 2015-12-15 2021-07-06 Changzhou Tronly Advanced Electronic Materials Co., Ltd. Fluorene polyfunctional photoinitiator and preparation and use thereof, and photosensitive resin composition containing fluorene photoinitiator and use thereof
WO2018049976A1 (en) * 2016-09-13 2018-03-22 常州强力先端电子材料有限公司 Fluorene photoinitiator, preparation method therefor, photocurable composition having same, and use of same in photocuring field
EP3514135A4 (en) * 2016-09-13 2020-04-29 Changzhou Tronly Advanced Electronic Materials Co., Ltd. Fluorene photoinitiator, preparation method therefor, photocurable composition having same, and use of same in photocuring field
US10976660B2 (en) 2016-09-13 2021-04-13 Changzhou Tronly Advanced Electronic Materials Co , Ltd. Fluorene photoinitiator, preparation method therefor, photocurable composition having same, and use of same in photocuring field
US11118065B2 (en) 2017-02-17 2021-09-14 Changzhou Tronly Advanced Electronic Materials Co., Ltd. Fluorenylaminoketone photoinitiator, preparation method thereof, and UV photocurable composition containing same
CN109265418A (en) * 2018-09-19 2019-01-25 华南理工大学 A kind of room temperature phosphorimetry material based on dibenzofurans and its preparation method and application containing carbonyl
CN109265418B (en) * 2018-09-19 2023-02-14 华南理工大学 Carbonyl-containing dibenzofuran-based room temperature phosphorescent material and preparation method and application thereof

Also Published As

Publication number Publication date
BE701017A (en) 1968-01-08
NL6709076A (en) 1968-01-23
DE1695743A1 (en) 1971-04-22
CH491848A (en) 1970-06-15

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Legal Events

Date Code Title Description
429A Application made for amendment of specification (sect. 29/1949)
429H Application (made) for amendment of specification now open to opposition (sect. 29/1949)
429D Case decided by the comptroller ** specification amended (sect. 29/1949)
SPA Amended specification published
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees