http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1459210-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_5af2e603d5fc3208f7f60a3e5efe4af6 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D221-16 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D221-20 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D221-16 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D221-20 |
| filingDate | 1973-12-18-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1976-12-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1459210-A |
| titleOfInvention | Method for the synthesis of plus-minus-glaziovine |
| abstract | 1459210 Glaziovine SIPHAR SA 18 Dec 1973 [22 Dec 1972] 58662/73 Heading C2C (Œ)-Glaziovine of Formula (I) is prepared according to the following reaction scheme wherein R is a hydrogen atom or an alkyl group having from one to four carbon atoms, R 1 is an alkyl group having from one to four carbon atoms, R 2 is a hydrogen atom or an aliphatic or aromatic acyl group, e.g. the acetyl or benzoyl group, characterized by comprising the steps of subjecting the 6,7-dimethoxy-2-methyl- 1,2,3,4 - tetrahydroisoquinolinyl - 1 - acetic acid of Formula (13) or an ester thereof to cyclization and selective demethylation of the 7-methoxy group by heating in polyphosphoric acid to obtain the tricyclo hydroxyketone of formula (12), bringing the compound (12) to react with a phosphorus ylide of Formula (14) according to the Wittig reaction in a solution in dimethylsulphoxide at 20-25‹ C. and for 5-12 hours, by addition of a solution of ylide (14) as obtained from triphenylmethoxymethylphosphonium chloride and sodium methylsulphinylmethide in an amount of 2À5-5 mol of ylide per mol of hydroxyketone to obtain an enol-ether of Formula (15), converting the enol-ether, by acidic hydrolysis, into the aldehyde of Formula (16), condensing the aldehydc (16) with methyl vinyl ketone in the presence of a basic catalyst selected from alkali metal hydroxides and alcoholates; quaternary ammonium hydroxides; and strong organic tertiary bases according to the Robinson ring-formation reaction to obtain the novel (Œ)-dihydroglaziovine of Formula (17), (R 2 =H); brominating an O-acyl-derative of (Œ)-dihydroglaziovine of Formula (17) (R 2 = aliphatic or aromatic acyl) with bromine or N-bromosuccinimide in the presence of 5-10 mols of a strong mineral acid per mole of compound to be brominated in an inert solvent to give the corresponding bromo derivative of Formula (18) and subjecting the latter to dehydrohalogenation and saponification to obtain (Œ)-glaziovine of Formula (1). (Œ)Glaziovine has tranquillizing and antianxiety activity. |
| priorityDate | 1972-12-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 43.