GB2569412A8 - Preparation of bimanes and chlorination of pyrazolinones - Google Patents

Preparation of bimanes and chlorination of pyrazolinones Download PDF

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Publication number
GB2569412A8
GB2569412A8 GB1808695.9A GB201808695A GB2569412A8 GB 2569412 A8 GB2569412 A8 GB 2569412A8 GB 201808695 A GB201808695 A GB 201808695A GB 2569412 A8 GB2569412 A8 GB 2569412A8
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GB
United Kingdom
Prior art keywords
pyrazolinone
bimanes
chlorinating
group
chloropyrazolinone
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.)
Granted
Application number
GB1808695.9A
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GB2569412A (en
GB201808695D0 (en
GB2569412B (en
Inventor
Neogi Ishita
Jyoti Partha
Grynszpan Falvio
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Individual
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Individual
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Publication of GB201808695D0 publication Critical patent/GB201808695D0/en
Publication of GB2569412A publication Critical patent/GB2569412A/en
Publication of GB2569412A8 publication Critical patent/GB2569412A8/en
Application granted granted Critical
Publication of GB2569412B publication Critical patent/GB2569412B/en
Expired - Fee Related legal-status Critical Current
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B39/00—Halogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

A method of chlorinating a pyrazolinone in the 4 position, comprising: (a) providing a pyrazolinone having a structure I: (b) contacting the pyrazolinone with a solid chlorination agent for a period of time, said contacting in the absence of a solvent; thereby chlorinating said pyrazolinone in the 4 position, yielding a 4-chloropyrazolinone having a structure II: wherein R1 and R2 are independently any suitable substituent is provided. R1 and R2 may be independently selected from the group consisting of: hydrogen, branched alkyl groups; straight alkyl groups; alkene groups, alkyne group and nitrile. The solid chlorinating agent may be selected from the group trichloroisocyanuric acid (TCCA), tert-butyl hypochlorite and N-chlorosuccinimide (NCS). A method of preparing bimanes (1,5-diazabicyclo[3.3.0]octadienediones) from said 4-chloropyrazolinone is described. A method of brominating said bimanes to form mono-bromo bimane (compound 6, figure 6) is also described.
GB1808695.9A 2017-06-04 2018-05-29 Chlorination of pyrazolinones Expired - Fee Related GB2569412B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201762514847P 2017-06-04 2017-06-04
US201762597448P 2017-12-12 2017-12-12

Publications (4)

Publication Number Publication Date
GB201808695D0 GB201808695D0 (en) 2018-07-11
GB2569412A GB2569412A (en) 2019-06-19
GB2569412A8 true GB2569412A8 (en) 2019-07-10
GB2569412B GB2569412B (en) 2020-04-01

Family

ID=62812422

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1808695.9A Expired - Fee Related GB2569412B (en) 2017-06-04 2018-05-29 Chlorination of pyrazolinones

Country Status (1)

Country Link
GB (1) GB2569412B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111992246B (en) * 2020-07-31 2022-12-20 江苏盈天环保科技有限公司 Supported photocatalyst containing syn- (Me, me) Bimane structure

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1980000565A1 (en) * 1978-09-05 1980-04-03 E Kosower 1,5-diazabicyclo(3.3.0)octadienedione derivatives,preparation and use thereof as fluorescent labelling agents
JP2998707B2 (en) * 1997-07-09 2000-01-11 日本電気株式会社 Organic electroluminescence device

Also Published As

Publication number Publication date
GB2569412A (en) 2019-06-19
GB201808695D0 (en) 2018-07-11
GB2569412B (en) 2020-04-01

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

Effective date: 20220529