GB1333464A - Production of 3,3 disubstituted azetidinones 2 - Google Patents

Production of 3,3 disubstituted azetidinones 2

Info

Publication number
GB1333464A
GB1333464A GB2386471A GB2386471A GB1333464A GB 1333464 A GB1333464 A GB 1333464A GB 2386471 A GB2386471 A GB 2386471A GB 2386471 A GB2386471 A GB 2386471A GB 1333464 A GB1333464 A GB 1333464A
Authority
GB
United Kingdom
Prior art keywords
radical
denotes
alternatively
cycloaliphatic
aliphatic
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
GB2386471A
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik 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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB1333464A publication Critical patent/GB1333464A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams

Landscapes

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

Abstract

1333464 Azetidinones BADISCHE ANILIN- & SODA-FABRIK AG 19 April 1971 [14 March 1970] 23864/71 Heading C2C 3,3 - Disubstituted azetidinones-(2) having the general formula where R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP> and R<SP>4</SP> may be identical or different and each denotes an aliphatic, cycloaliphatic, araliphatic or heterocyclic radical; R<SP>3</SP> and/or R<SP>4</SP> may alternatively denote a hydrogen atom; R<SP>1</SP> and R<SP>2</SP> together with the adjacent carbon atom or R<SP>1</SP> and R<SP>3</SP> together with the two adjacent carbon atoms may alternatively form a cycloaliphatic or heterocyclic ring; R<SP>1</SP>, R<SP>2</SP> and/or R<SP>4</SP> may alternatively denote an aromatic radical; R<SP>4</SP> may alternatively denote alkylsulphonyl, arylsulphonyl, any of the radicals -NR<SP>5</SP>R<SP>6</SP>, -CONR<SP>5</SP>R<SP>6</SP> and -COOR<SP>5</SP> (where the individual radicals R<SP>5</SP> and R<SP>6</SP> may be identical or different and each denotes a hydrogen atom, an aliphatic, cycloaliphatic, araliphatic or aromatic radical, R<SP>6</SP> together with the adjacent nitrogen atom and the radical R<SP>5</SP> adjacent thereto may alternatively form a heterocyclic ring, or R<SP>6</SP> may alternatively denote a sulphonic acid group or an arylsulphonyl radical), the radical or the radical (where R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> have the above meanings, n denotes 1 or an integer greater than 1, and R<SP>7</SP> denotes an aliphatic, cycloaliphatic or aromatic radical), is prepared by dehydrohalogenation of a #-halocarboxamide having the general formula where R<SP>8</SP> has the same meaning as R<SP>4</SP> or denotes the radical or the radical where X is halogen in the presence of a tertiary amine whose pK B value is less than 8. The #- halocarboxamide may be prepared in situ. without isolation from a halocarboxylic halide with R<SP>10</SP>NH 2 where R<SP>10</SP> is as for R<SP>8</SP> or is -NH 2 or -R<SP>7</SP>(NH 2 ) n in the presence of a teriary amine having a pK B value less than 8. 1,5 - Diaza - 2,6 - dioxo - 3,3,7,7 - tetramethyl - bicyclo[3,3,0]octane is a by-product when N,N<SP>1</SP>-bis-bromopivaloyl hydrazide is treated with Et 3 N (Example 21).
GB2386471A 1970-03-14 1971-04-19 Production of 3,3 disubstituted azetidinones 2 Expired GB1333464A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19702012216 DE2012216A1 (en) 1970-03-14 1970-03-14 Process for the preparation of 3,3-disubstituted beta-lactams

Publications (1)

Publication Number Publication Date
GB1333464A true GB1333464A (en) 1973-10-10

Family

ID=5765113

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2386471A Expired GB1333464A (en) 1970-03-14 1971-04-19 Production of 3,3 disubstituted azetidinones 2

Country Status (5)

Country Link
BE (1) BE764161A (en)
CH (1) CH546235A (en)
DE (1) DE2012216A1 (en)
FR (1) FR2084563A5 (en)
GB (1) GB1333464A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5705456A (en) * 1995-12-01 1998-01-06 Zeneca Limited Herbicides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5705456A (en) * 1995-12-01 1998-01-06 Zeneca Limited Herbicides

Also Published As

Publication number Publication date
DE2012216A1 (en) 1971-09-23
CH546235A (en) 1974-02-28
FR2084563A5 (en) 1971-12-17
BE764161A (en) 1971-09-13

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Legal Events

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