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GB1434714A - 3-amino-prop-1-enes methods for their preparation - Google Patents

3-amino-prop-1-enes methods for their preparation

Info

Publication number
GB1434714A
GB1434714A GB1516973A GB6031571A GB1434714A GB 1434714 A GB1434714 A GB 1434714A GB 1516973 A GB1516973 A GB 1516973A GB 6031571 A GB6031571 A GB 6031571A GB 1434714 A GB1434714 A GB 1434714A
Authority
GB
United Kingdom
Prior art keywords
group
hydrogen
prepared
biphenyl
alkyl
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
GB1516973A
Inventor
Paul A Barrett
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation 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
Priority to BE793469D priority Critical patent/BE793469A/en
Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB1516973A priority patent/GB1434714A/en
Priority to AR245898A priority patent/AR205875A1/en
Priority to US05/314,845 priority patent/US3932663A/en
Priority to NL7217642A priority patent/NL7217642A/xx
Priority to CH1896272A priority patent/CH598191A5/xx
Priority to ES410122A priority patent/ES410122A1/en
Priority to CS729021A priority patent/CS188158B2/en
Priority to FI3668/72A priority patent/FI58490C/en
Priority to SE7217048A priority patent/SE395142B/en
Priority to IL41200A priority patent/IL41200A/en
Priority to ZA729157A priority patent/ZA729157B/en
Priority to JP48004159A priority patent/JPS5750774B2/ja
Priority to FR7246606A priority patent/FR2166122B1/fr
Priority to DK650972A priority patent/DK143897C/en
Priority to DE2263817A priority patent/DE2263817A1/en
Priority to HUWE475A priority patent/HU166958B/hu
Priority to CA160,202A priority patent/CA1009255A/en
Priority to AR250872A priority patent/AR206205A1/en
Priority to ES419165A priority patent/ES419165A1/en
Priority to AR256434A priority patent/AR205550A1/en
Priority to US05/617,294 priority patent/US4079081A/en
Priority to SE7601707A priority patent/SE410311B/en
Priority to CS762115A priority patent/CS188195B2/en
Publication of GB1434714A publication Critical patent/GB1434714A/en
Priority to CA258,457A priority patent/CA1040647A/en
Priority to CS767402A priority patent/CS188197B2/en
Priority to CS767403A priority patent/CS188198B2/en
Priority to CS767404A priority patent/CS188199B2/en
Priority to CH1050877A priority patent/CH609326A5/xx
Priority to CH1050977A priority patent/CH598192A5/xx
Priority to CH1050577A priority patent/CH599105A5/xx
Priority to CH1050677A priority patent/CH609325A5/xx
Priority to DK191779A priority patent/DK191779A/en
Priority to FI794000A priority patent/FI794000A7/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/535—Organo-phosphoranes
    • C07F9/5352—Phosphoranes containing the structure P=C-
    • 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
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • 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
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C07C49/788—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with keto groups bound to a condensed ring system
    • 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
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
    • 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
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1434714 1,1 - Diaryl - 3 - amino - prop - 1- enes WELLCOME FOUNDATION Ltd 29 March 1973 [29 Dec 1971 23 Oct 1972 29 Dec 1972] 60315/71 48748/72 and 15169/73 Heading C2C Novel compounds (I) and their salts in which each of R<SP>1</SP> and R<SP>2</SP> is an optionally substituted biphenylyl, fluorenyl or phenyl group with the proviso that both R<SP>1</SP> and R<SP>2</SP> do not represent a substituted biphenylyl or substituted or unsubstituted phenyl group and that when one of R<SP>1</SP> and R<SP>2</SP> is a substituted biphenyl group the other is an optionally substituted phenyl group and R<SP>3</SP> and R<SP>4</SP> are hydrogen, C 1-4 alkyl or benzyl are prepared from a compound (V) R<SP>1</SP>R<SP>2</SP>C(Q)-CH(G)M by (1) (i) when Q and G represent a bond and (a) M is CN, CYNR<SP>3</SP>R<SP>4</SP> (where Y is O or S) CH 2 A (where A is NR<SP>3</SP>COR<SP>9</SP> or NR<SP>3</SP>COOR where R is C 1-4 alkyl and R<SP>9</SP> is hydrogen or C 1-3 alkyl) by selective reduction so that the R<SP>1</SP>R<SP>2</SP>C=C moiety is unreduced (b) M is CH 2 Z (in which Z is a leaving group preferably bromo or tosyloxy) by reaction with an amine HNR 3 R 4 (c) M is CH 2 NR 3 R 4 (in which one or both R 3 and R 4 are hydrogen) by mono- or dialkylation or (2) M is CH 2 NR<SP>3</SP>B (in which B is a protecting group) by removing the group B or (ii) when Q is a nucleophilic group preferably hydroxy, G is hydrogen and M is CH 2 NR 3 R 4 by eliminating a molecule of GQ from a molecule of compound (V), (2) reacting a phosphorane VI R<SP>6</SP>R<SP>7</SP>R<SP>8</SP>P=CH 2 -CH 2 NR<SP>3</SP>R<SP>4</SP> in which R 6 , R 7 , R 8 are alkyl or phenyl groups with a ketone R 1 R 2 CO or (3) a combination of method (1)(i)(c) with any other method defined above. In compounds I prepared R 1 is preferably a 4-biphenyl group and R 2 a phenyl group both optionally substituted by halogen or nitro groups or R 1 and R 2 are both 4-biphenyl groups; R 1 may also be 2-fluorenyl or 2-biphenyl; R 3 and R 4 are hydrogen and/or methyl. When R 1 and R 2 are different the cis and trans isomers may be isolated. Compounds (XX) in which R 10 is nitro, halogen or phenyl and R 11 is hydrogen or halogen are prepared by Friedal Crafts reaction between the appropriate biphenyl and a benzoyl chloride or between an appropriate benzene derivative and a biphenylyl carbonyl chloride and 2-p-chlorobenzoylfluorene is prepared by a Friedal-Crafts reaction between fluorene and p-chlorobenzoyl chloride. 3,3-Bis- (4 - biphenylyl) - prop - 2 - enyl tosylate is prepared by esterification of the corresponding alcohol. Compounds I are active against Trypansoma cruzi and form with a carrier a pharmaceutical composition which may be administered orally or parenterally.
GB1516973A 1971-12-29 1971-12-29 3-amino-prop-1-enes methods for their preparation Expired GB1434714A (en)

Priority Applications (34)

Application Number Priority Date Filing Date Title
BE793469D BE793469A (en) 1971-12-29 TRYPANOCIDAL COMPOUNDS
GB1516973A GB1434714A (en) 1971-12-29 1971-12-29 3-amino-prop-1-enes methods for their preparation
AR245898A AR205875A1 (en) 1971-12-29 1972-01-01 METHOD TO PREPARE SUBSTITUTED 3-AMINOPROP-1-ENSO AND COMPOUNDS TO CARRY IT OUT
US05/314,845 US3932663A (en) 1971-12-29 1972-12-13 Certain 3-amino-prop-1-enes for treating Trypanosoma cruzi infections
NL7217642A NL7217642A (en) 1971-12-29 1972-12-27
CS729021A CS188158B2 (en) 1971-12-29 1972-12-28 Method of producing substituted 3-aminoprop-1-enes
ES410122A ES410122A1 (en) 1971-12-29 1972-12-28 Certain 3-amino-prop-1-enes for treating Trypanosoma cruzi infections
CH1896272A CH598191A5 (en) 1971-12-29 1972-12-28
FI3668/72A FI58490C (en) 1971-12-29 1972-12-28 FOERFARANDE FOER FRAMSTAELLNING AV NYA TERAPEUTISKT ANVAENDBARA SUBSTITUERADE 2-AMINO-PROP-1-ENER-OCH DERAS CIS- OCH TRANS-ISOMERER OCH DERAS SYRAADDITIONSSALTER
SE7217048A SE395142B (en) 1971-12-29 1972-12-28 WAY TO PRODUCE A SUBSTITUTED 3-AMINO-PROP-1-EN
IL41200A IL41200A (en) 1971-12-29 1972-12-28 Substituted 3-amino-prop-1-enes,their preparation and pharmaceutical compositions containing them
ZA729157A ZA729157B (en) 1971-12-29 1972-12-28 3-amino-prop-1-enes
JP48004159A JPS5750774B2 (en) 1971-12-29 1972-12-28
FR7246606A FR2166122B1 (en) 1971-12-29 1972-12-28
DK650972A DK143897C (en) 1971-12-29 1972-12-28 ANALOGY PROCEDURE FOR PREPARING SUBSTITUTED 3-AMINO-PROP-1 UNES
DE2263817A DE2263817A1 (en) 1971-12-29 1972-12-28 ORGANIC COMPOUNDS
CA160,202A CA1009255A (en) 1971-12-29 1972-12-29 3-amino-prop-1-enes and the preparation thereof
HUWE475A HU166958B (en) 1971-12-29 1972-12-29
AR250872A AR206205A1 (en) 1971-12-29 1973-01-01 A METHOD TO PREPARE SUBSTITUTE AND INTERMEDIARY 3-AMINO-PROP-1-ENSO TO CARRY OUT
ES419165A ES419165A1 (en) 1971-12-29 1973-09-28 Certain 3-amino-prop-1-enes for treating Trypanosoma cruzi infections
AR256434A AR205550A1 (en) 1971-12-29 1974-01-01 METHOD FOR PREPARING 3 - AMINO - PROP - 1 - SUBSTITUTED ENSO AND COMPOUNDS TO CARRY IT OUT
US05/617,294 US4079081A (en) 1971-12-29 1975-09-29 1,1-Diaryl-3-amino-prop-1-enes
SE7601707A SE410311B (en) 1971-12-29 1976-02-16 OUTPUT FOR THE PRODUCTION OF SUBSTITUTED 3-AMINO-PROP-1 ENES
CS762115A CS188195B2 (en) 1971-12-29 1976-04-01 Method of producing substituted 3-aminoprop-1-enes
CA258,457A CA1040647A (en) 1971-12-29 1976-08-05 Intermediates for novel 3-amino-prop-1-enes
CS767402A CS188197B2 (en) 1971-12-29 1976-11-17 Method of producing substituted 3-aminoprop-1-enes
CS767403A CS188198B2 (en) 1971-12-29 1976-11-17 Method of producing substituted 3-aminoprop-1-enes
CS767404A CS188199B2 (en) 1971-12-29 1976-12-28 Method of producing substituted 3-aminoprop-1-enes
CH1050877A CH609326A5 (en) 1971-12-29 1977-08-29
CH1050977A CH598192A5 (en) 1971-12-29 1977-08-29
CH1050577A CH599105A5 (en) 1971-12-29 1977-08-29
CH1050677A CH609325A5 (en) 1971-12-29 1977-08-29
DK191779A DK191779A (en) 1971-12-29 1979-05-09 CHEMICAL COMPOUNDS FOR USE AS INTERMEDIATE & R
FI794000A FI794000A7 (en) 1971-12-29 1979-12-20 New, substituted intermediates used in the preparation of 3-amino-prop-1-enes.

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB1516973A GB1434714A (en) 1971-12-29 1971-12-29 3-amino-prop-1-enes methods for their preparation
GB4874872 1972-10-23
GB1516973 1972-12-29

Publications (1)

Publication Number Publication Date
GB1434714A true GB1434714A (en) 1976-05-05

Family

ID=27257227

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1516973A Expired GB1434714A (en) 1971-12-29 1971-12-29 3-amino-prop-1-enes methods for their preparation

Country Status (1)

Country Link
GB (1) GB1434714A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0262919A3 (en) * 1986-09-30 1988-07-20 Raychem Limited Preparation of aryl carbonyl compounds
WO1994005618A1 (en) * 1992-08-31 1994-03-17 Eastman Kodak Company Process for the production of diiodoketones
CN115368244A (en) * 2021-05-17 2022-11-22 北京鼎材科技有限公司 The synthetic method of 2-aryl-2-(4-aminophenyl) propane

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0262919A3 (en) * 1986-09-30 1988-07-20 Raychem Limited Preparation of aryl carbonyl compounds
US4898983A (en) * 1986-09-30 1990-02-06 Raychem Limited Preparation of aryl carbonyl compounds
WO1994005618A1 (en) * 1992-08-31 1994-03-17 Eastman Kodak Company Process for the production of diiodoketones
CN115368244A (en) * 2021-05-17 2022-11-22 北京鼎材科技有限公司 The synthetic method of 2-aryl-2-(4-aminophenyl) propane

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee