GB1180876A - Process for the Preparation of 1-Substituted 3-Imino-Pyrazolidines - Google Patents

Process for the Preparation of 1-Substituted 3-Imino-Pyrazolidines

Info

Publication number
GB1180876A
GB1180876A GB3903368A GB3903368A GB1180876A GB 1180876 A GB1180876 A GB 1180876A GB 3903368 A GB3903368 A GB 3903368A GB 3903368 A GB3903368 A GB 3903368A GB 1180876 A GB1180876 A GB 1180876A
Authority
GB
United Kingdom
Prior art keywords
imino
pyrazolidine
pyrazolidines
substituted
acid
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
GB3903368A
Inventor
Helmut Dorn
Albrecht Otto
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.)
Akademie der Wissenschaften der DDR
Original Assignee
Akademie der Wissenschaften der DDR
Deutsche Akademie der Wissenschaften zu Berlin
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 Akademie der Wissenschaften der DDR, Deutsche Akademie der Wissenschaften zu Berlin filed Critical Akademie der Wissenschaften der DDR
Priority to GB3903368A priority Critical patent/GB1180876A/en
Publication of GB1180876A publication Critical patent/GB1180876A/en
Expired legal-status Critical Current

Links

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

1,180,876. 3 - Imino - pyrazolidine; pyrazolidinones. DEUTSCHE AKADEMIE DER WISSENSCHAFTEN ZU BERLIN. 15 Aug., 1968, No. 39033/68. Heading C2C. 3-Imino-pyrazolidines of the formula wherein R and R<SP>1</SP> represent hydrogen or alkyl, polyhydroxyalkyl, #-carboxyalkyl, #-alkoxycarbonyl-alkyl, phenyl, substituted phenyl or heterocyclic radicals, or R and R<SP>1</SP> together form a cycloalkyl ring and R<SP>11</SP> is hydrogen or an alkyl radical, or the acid addition salts thereof, are prepared by hydrogenating a 1 : 1 molar mixture of a pyrazolidine of the formula or an acid addition salt thereof, and a carbonyl compound R.CO.R<SP>1</SP> in a solvent at 0-40‹ C. in the presence of a metallic hydrogenation catalyst until 1 mol. of hydrogen has been taken up. When the starting pyrazolidine is the free base, the reaction is preferably effected in the presence of 1-2 mols. of an acid, per mol. pyrazolidine. The starting pyrazolidines may be prepared by reacting aqueous hydrazine with the required α,#-unsaturated nitrile to obtain the corresponding #-hydrazinopropionitrile which cyclizes under acidic conditions to the 3-imino-pyrazolidine. The 1-substituted- 3-imino pyrazolidines obtained by the hydrogenation process may be hydrolysed by heating with an acid, e.g. H 2 SO 4 , to the corresponding 1-substituted pyrazolidin-3-ones. Examples describe the preparation of 1-iso-propyl-, 1- cyclohexyl-, 1-desoxy-D-mannite-, 1-benzyl- and 1 - # - phenylethyl - 3 - imino - pyrazolidines, and the corresponding pyrazolidinones, from acetone, cyclohexanone, D-mannose, benzaldehyde and phenylacetaldehyde.
GB3903368A 1968-08-15 1968-08-15 Process for the Preparation of 1-Substituted 3-Imino-Pyrazolidines Expired GB1180876A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3903368A GB1180876A (en) 1968-08-15 1968-08-15 Process for the Preparation of 1-Substituted 3-Imino-Pyrazolidines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3903368A GB1180876A (en) 1968-08-15 1968-08-15 Process for the Preparation of 1-Substituted 3-Imino-Pyrazolidines

Publications (1)

Publication Number Publication Date
GB1180876A true GB1180876A (en) 1970-02-11

Family

ID=10407198

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3903368A Expired GB1180876A (en) 1968-08-15 1968-08-15 Process for the Preparation of 1-Substituted 3-Imino-Pyrazolidines

Country Status (1)

Country Link
GB (1) GB1180876A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5883251A (en) * 1995-04-20 1999-03-16 G. D. Searle & Co. Azepine derivatives useful as nitric oxide synthase inhibitors
US5958958A (en) * 1997-07-22 1999-09-28 G.D. Searle & Co. 1,2,4-oxa diazolino and 1,24-oxa diazolidion heterocycles as useful nitric oxide synthase inhibitors
US6344473B1 (en) 2000-08-07 2002-02-05 G.D. Searle & Co. Imidazoles useful as nitric oxide synthase inhibitors
US6489323B1 (en) 1998-06-10 2002-12-03 G.D. Searle & Co. Heterobicyclic and tricyclic nitric oxide synthase inhibitors

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5883251A (en) * 1995-04-20 1999-03-16 G. D. Searle & Co. Azepine derivatives useful as nitric oxide synthase inhibitors
US5958958A (en) * 1997-07-22 1999-09-28 G.D. Searle & Co. 1,2,4-oxa diazolino and 1,24-oxa diazolidion heterocycles as useful nitric oxide synthase inhibitors
US5981556A (en) * 1997-07-22 1999-11-09 G.D. Searle & Co. 1,3-diazolino and 1,3-diazolidino heterocycles as useful nitric oxide synthase inhibitors
US6136829A (en) * 1997-07-22 2000-10-24 G.D. Searle & Co. Oxathiadiazole derivatives usful as iNOS inhibitors
US6489323B1 (en) 1998-06-10 2002-12-03 G.D. Searle & Co. Heterobicyclic and tricyclic nitric oxide synthase inhibitors
US6344473B1 (en) 2000-08-07 2002-02-05 G.D. Searle & Co. Imidazoles useful as nitric oxide synthase inhibitors

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