GB1427541A - Cyclopenteno-b-furan derivatives - Google Patents

Cyclopenteno-b-furan derivatives

Info

Publication number
GB1427541A
GB1427541A GB203273*[A GB203273A GB1427541A GB 1427541 A GB1427541 A GB 1427541A GB 203273 A GB203273 A GB 203273A GB 1427541 A GB1427541 A GB 1427541A
Authority
GB
United Kingdom
Prior art keywords
cyclopenta
alkyl
formula
furan
hexahydro
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
GB203273*[A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB203273*[A priority Critical patent/GB1427541A/en
Priority to ZA740023A priority patent/ZA7423B/en
Priority to NL7400399A priority patent/NL7400399A/xx
Priority to FR7401116A priority patent/FR2213938B1/fr
Priority to CH53074A priority patent/CH584707A5/xx
Priority to DE2401763A priority patent/DE2401763A1/en
Priority to JP49007768A priority patent/JPS49101369A/ja
Publication of GB1427541A publication Critical patent/GB1427541A/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
    • C07D307/93—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 condensed with a ring other than six-membered
    • C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1427541 Cyclopenta[b]furanones IMPERIAL CHEMICAL INDUSTRIES Ltd 21 Dec 1973 [15 Jan 1973] 2032/73 Heading C2C Novel cyclopenta[b]furanones of the Formula I and absolute stereochemistry wherein R<SP>1</SP> is C 4-10 alkyl, C 4-10 alkenyl, a radical of the formula -A<SP>1</SP>-OR<SP>2</SP>, wherein A<SP>1</SP> is C 1-9 alkylene, and R<SP>2</SP> is C 1-9 alkyl or C 5-7 cycloalkyl, provided A<SP>1</SP> and R<SP>2</SP> together contain not more than 10 C atoms; a radical of the formula -A<SP>2</SP>R<SP>3</SP>, wherein A<SP>2</SP> is a direct bond or C 1-3 alkylene, and R<SP>3</SP> is aryl optionally substituted by halogen, NO 2 , C 1-3 alkyl, C 1-3 haloalkyl, C 1-3 alkoxy or di(C 1-3 alkyl)-amino; a radical of the formula -A<SP>3</SP>.A<SP>4</SP>.R<SP>4</SP>, wherein A<SP>3</SP> is C 1-3 alkylene optionally substituted by 1 or 2 C 1-3 alkyl radicals, A<SP>4</SP> is O, S, SO or C 1-4 alkylimino, and R<SP>4</SP> is aryl, benzyl or furfuryl optionally substituted by OH, NO 2 , phenyl, halogen, C 1-4 alkyl, C 2-4 alkenyl, C 1-4 haloalkyl, C 1-4 alkoxy, C 2-4 alkenyloxy, C 1-4 acylamino or di- (1-3 alkyl)amino; or a radical of the formula -A<SP>3</SP>.A<SP>5</SP>.R<SP>5</SP>, wherein A<SP>5</SP> is O, S, SO, SO 2 , NH, C 1-4 alkylimino or a direct bond, or A<SP>3</SP> and A<SP>5</SP> together are a direct bond, and R<SP>5</SP> is an aromatic heterocyclic radical of one or two 5- or 6- membered rings, containing in one ring only, 1 or 2 non-adjacent hetero-atoms, and optionally bearing 1 to 3 alkyl radicals or halogen atoms as substituents, are prepared by oxidizing optically active hydroxy-enols of the Formula II obtained by hydrolysing the corresponding 5α- (p-phenylbenzoyloxy) - 4# - (3 - R<SP>1</SP> - 3 - hydroxytrans - 1 - propenyl) - 3,3a#.4.5.6,6a# - hexahydro - 2H - cyclopenta[b]furan - 2 - ones, which are prepared by reducing the corresponding 5x - (p - phenylbenzoyloxy) - 4# - (3 - R<SP>1</SP> - 3- oxo - trans - 1 - propenyl) - 3,3a#,4.5.6,6a#- hexahydro - 2H - cyclopenta[b]furan - 2 - ones, resulting from the reaction of phosphonates of the formula (CH 3 O) 2 PO.CH 2 COR<SP>1</SP> in the presence of strong bases with 5α-(p-phenylbenzoyloxy) - 3,3a#,4.5.6,6a# - hexahydro - 2H - cyclopenta[b]furan - 4# - carbaldehyde, obtained hydrolysing 5α - (p - phenylbenzoyloxy) - 3,3a#,- 4.5.6,6a# - hexahydro - 4# - dimethoxymethyl- 2H - cyclopenta[b]furan - 2 - one, which is prepared by deiodinating 5α-(p-phenylbenzoyloxy)- 6 - iodo - 3,3a#,4.5.6,6a,# - hexahydro - 4#- dimethoxymethyl - 2H - cyclopenta[b]furan - 2- one, obtained by acylating 5α-hydroxy-6-iodo- 3,3a#,4.5.6,6a# - hexahydro - 4# - dimethoxymethyl - 2H - cyclopenta[b]furan-2-one, resulting from the Bayer-Villiger oxidation and rearrangement with potassium tri-iodide of (-)-7- dimethoxymethylbicyclo[2,2,1]hept- 5 - en - 2 - one, which is prepared by oxidizing (-)-7-dimethoxymethylbicyclo[2,2,1]hept- 5 - en - 2 - endo - ol, resulting from the hydrolysis of the corresponding optically active hemi-phthalate, obtained by resolution of the amphetamine salt and hydrolysis of the resolved salt. (Œ) - 7 - Dimethoxymethylbicyclo[2,2,1]- hept - 5 - en - 2 - endo - ol is obtained by reducing (Œ) - 7 - dimethoxymethylbicyclo- [2,2,1]hept-5-en-2-one.
GB203273*[A 1973-01-15 1973-01-15 Cyclopenteno-b-furan derivatives Expired GB1427541A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
GB203273*[A GB1427541A (en) 1973-01-15 1973-01-15 Cyclopenteno-b-furan derivatives
ZA740023A ZA7423B (en) 1973-01-15 1974-01-02 Chemical intermediates
NL7400399A NL7400399A (en) 1973-01-15 1974-01-11
FR7401116A FR2213938B1 (en) 1973-01-15 1974-01-14
CH53074A CH584707A5 (en) 1973-01-15 1974-01-15
DE2401763A DE2401763A1 (en) 1973-01-15 1974-01-15 OPTICALLY ACTIVE HYDROXYENONE
JP49007768A JPS49101369A (en) 1973-01-15 1974-01-16

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB203273*[A GB1427541A (en) 1973-01-15 1973-01-15 Cyclopenteno-b-furan derivatives

Publications (1)

Publication Number Publication Date
GB1427541A true GB1427541A (en) 1976-03-10

Family

ID=9732416

Family Applications (1)

Application Number Title Priority Date Filing Date
GB203273*[A Expired GB1427541A (en) 1973-01-15 1973-01-15 Cyclopenteno-b-furan derivatives

Country Status (7)

Country Link
JP (1) JPS49101369A (en)
CH (1) CH584707A5 (en)
DE (1) DE2401763A1 (en)
FR (1) FR2213938B1 (en)
GB (1) GB1427541A (en)
NL (1) NL7400399A (en)
ZA (1) ZA7423B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1502610A (en) * 1974-12-12 1978-03-01 Ici Ltd Process for the preparation of prostaglandin intermediate

Also Published As

Publication number Publication date
FR2213938B1 (en) 1977-06-10
CH584707A5 (en) 1977-02-15
FR2213938A1 (en) 1974-08-09
DE2401763A1 (en) 1974-07-18
NL7400399A (en) 1974-07-17
JPS49101369A (en) 1974-09-25
ZA7423B (en) 1974-11-27

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Legal Events

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