FR2434151A1 - PROCESS FOR PRODUCING PYRROLIDINE-2-ONES FROM 3-PYRROLINE-2-ONES AND PROCESS FOR PRODUCING 3-PYRROLINE-2-ONES NECESSARY FOR THIS PURPOSE - Google Patents
PROCESS FOR PRODUCING PYRROLIDINE-2-ONES FROM 3-PYRROLINE-2-ONES AND PROCESS FOR PRODUCING 3-PYRROLINE-2-ONES NECESSARY FOR THIS PURPOSEInfo
- Publication number
- FR2434151A1 FR2434151A1 FR7914907A FR7914907A FR2434151A1 FR 2434151 A1 FR2434151 A1 FR 2434151A1 FR 7914907 A FR7914907 A FR 7914907A FR 7914907 A FR7914907 A FR 7914907A FR 2434151 A1 FR2434151 A1 FR 2434151A1
- Authority
- FR
- France
- Prior art keywords
- ones
- pyrroline
- producing
- pyrrolidine
- necessary
- 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
Links
- CDCHBOQVXIGZHA-UHFFFAOYSA-N 1,2-dihydropyrrol-5-one Chemical class O=C1NCC=C1 CDCHBOQVXIGZHA-UHFFFAOYSA-N 0.000 abstract 1
- 230000004071 biological effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 1
- 150000003180 prostaglandins Chemical class 0.000 abstract 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical class O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
-
- 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
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Abstract
L'invention concerne la synthèse de composés hétérocycliques doués d'une activité biologique. On soumet des N-aroylméthylacétamides à une cyclisation sous N2 en milieu basique pour obtenir des 3-pyrroline-2-ones qu'une hydrogénation catalytique transforme en les pyrrolidine-2-ones correspondantes. Les composés ainsi obtenus agissent sur le système nerveux central ou ont une action analogue à celle des prostaglandines.The invention relates to the synthesis of heterocyclic compounds endowed with biological activity. N-aroylmethylacetamides are subjected to cyclization under N2 in a basic medium to obtain 3-pyrrolin-2-ones which catalytic hydrogenation transforms into the corresponding pyrrolidine-2-ones. The compounds thus obtained act on the central nervous system or have an action analogous to that of prostaglandins.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US91468278A | 1978-06-12 | 1978-06-12 | |
US1249679A | 1979-02-15 | 1979-02-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2434151A1 true FR2434151A1 (en) | 1980-03-21 |
FR2434151B3 FR2434151B3 (en) | 1982-04-30 |
Family
ID=26683628
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7914907A Granted FR2434151A1 (en) | 1978-06-12 | 1979-06-11 | PROCESS FOR PRODUCING PYRROLIDINE-2-ONES FROM 3-PYRROLINE-2-ONES AND PROCESS FOR PRODUCING 3-PYRROLINE-2-ONES NECESSARY FOR THIS PURPOSE |
Country Status (19)
Country | Link |
---|---|
AR (1) | AR222997A1 (en) |
AT (1) | ATA386679A (en) |
AU (1) | AU529479B2 (en) |
CA (1) | CA1108628A (en) |
CH (1) | CH650772A5 (en) |
DE (3) | DE2954236C2 (en) |
DK (1) | DK157847C (en) |
ES (1) | ES481315A1 (en) |
FI (1) | FI70209C (en) |
FR (1) | FR2434151A1 (en) |
GB (1) | GB2028307B (en) |
GR (1) | GR68438B (en) |
IL (1) | IL57266A (en) |
IT (1) | IT1116891B (en) |
NL (1) | NL7904584A (en) |
NO (1) | NO791943L (en) |
NZ (1) | NZ190705A (en) |
PT (1) | PT69716A (en) |
SE (1) | SE431644B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4943640A (en) * | 1983-10-14 | 1990-07-24 | The Dow Chemical Company | Preparation of 5-(1-alkyl-carbonyloxy)alkylpyrrolidin-2-one |
WO1990007499A1 (en) * | 1988-12-27 | 1990-07-12 | Ici Americas Inc. | Process for the preparation of 3-carboalkoxypyrrolidones |
US5021587A (en) * | 1990-01-24 | 1991-06-04 | Petrolite Corporation | Synthesis of N,3,4-trisubstituted-3-azoline-2-ones |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3272842A (en) * | 1965-06-25 | 1966-09-13 | Lilly Co Eli | Novel pyrrolinones |
GB1350582A (en) * | 1970-07-24 | 1974-04-18 | Ucb Sa | Cerivatives of 2-pyrrolidinone |
DE2413935A1 (en) | 1974-03-20 | 1975-10-16 | Schering Ag | 4- (POLYALCOXY-PHENYL) -2-PYRROLIDONE |
-
1979
- 1979-05-14 IL IL57266A patent/IL57266A/en unknown
- 1979-05-15 GR GR59088A patent/GR68438B/el unknown
- 1979-05-17 AR AR276559A patent/AR222997A1/en active
- 1979-05-28 AT AT793866A patent/ATA386679A/en not_active Application Discontinuation
- 1979-06-01 PT PT69716A patent/PT69716A/en unknown
- 1979-06-01 AU AU47670/79A patent/AU529479B2/en not_active Ceased
- 1979-06-06 ES ES481315A patent/ES481315A1/en not_active Expired
- 1979-06-08 CA CA329,322A patent/CA1108628A/en not_active Expired
- 1979-06-09 DE DE2954236A patent/DE2954236C2/de not_active Expired
- 1979-06-09 DE DE2954237A patent/DE2954237C2/de not_active Expired
- 1979-06-09 DE DE19792923553 patent/DE2923553A1/en active Granted
- 1979-06-11 GB GB7920275A patent/GB2028307B/en not_active Expired
- 1979-06-11 DK DK241779A patent/DK157847C/en not_active IP Right Cessation
- 1979-06-11 FR FR7914907A patent/FR2434151A1/en active Granted
- 1979-06-11 NO NO791943A patent/NO791943L/en unknown
- 1979-06-11 IT IT49373/79A patent/IT1116891B/en active
- 1979-06-11 SE SE7905079A patent/SE431644B/en not_active IP Right Cessation
- 1979-06-12 FI FI791866A patent/FI70209C/en not_active IP Right Cessation
- 1979-06-12 CH CH5496/79A patent/CH650772A5/en not_active IP Right Cessation
- 1979-06-12 NZ NZ190705A patent/NZ190705A/en unknown
- 1979-06-12 NL NL7904584A patent/NL7904584A/en not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
FR2434151B3 (en) | 1982-04-30 |
CA1108628A (en) | 1981-09-08 |
ATA386679A (en) | 1983-12-15 |
FI791866A (en) | 1979-12-13 |
IL57266A (en) | 1982-12-31 |
AR222997A1 (en) | 1981-07-15 |
DK241779A (en) | 1979-12-13 |
CH650772A5 (en) | 1985-08-15 |
AU529479B2 (en) | 1983-06-09 |
GB2028307B (en) | 1983-01-19 |
NZ190705A (en) | 1981-10-19 |
SE7905079L (en) | 1979-12-13 |
DK157847B (en) | 1990-02-26 |
NO791943L (en) | 1979-12-13 |
IT7949373A0 (en) | 1979-06-11 |
NL7904584A (en) | 1979-12-14 |
DE2923553C2 (en) | 1988-06-01 |
PT69716A (en) | 1979-07-01 |
FI70209B (en) | 1986-02-28 |
SE431644B (en) | 1984-02-20 |
DK157847C (en) | 1990-09-17 |
DE2954236C2 (en) | 1988-10-06 |
GR68438B (en) | 1981-12-30 |
IT1116891B (en) | 1986-02-10 |
ES481315A1 (en) | 1980-08-16 |
IL57266A0 (en) | 1979-09-30 |
DE2954237C2 (en) | 1989-09-21 |
FI70209C (en) | 1986-09-15 |
AU4767079A (en) | 1979-12-20 |
GB2028307A (en) | 1980-03-05 |
DE2923553A1 (en) | 1979-12-20 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |