http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1394374-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_6919d7172c27ca1f9a337af1ca2e3f42 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D215-20 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D455-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D471-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D215-08 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D215-20 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D215-08 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D471-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D455-04 |
| filingDate | 1972-05-17-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1975-05-14-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1394374-A |
| titleOfInvention | Pyrrolo-quinoline and pyrido-quinoline derivatives |
| abstract | 1394374 Pyrrolo[3,2,1-i, j]-quinolines; benzo- [i, j]-quinolizines PFIZER Ltd 15 May 1973 [17 May 1972] 31376/74 Divided out of 1394373 Heading C2C Novel compounds have the Formulµ I and II wherein R is a C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkanoyl, benzoyl, hydroxy, C 1-4 alkanoyloxy or cyano group or represents one or two halogen atoms; R<SP>1</SP> and R<SP>2</SP> each independently represents hydrogen or one or more halogen, C 1-4 alkyl, phenyl, oxo or thioxo (thione) substituents; and the dotted lines represent an optional bond in each ring, with the proviso that R is other than a single chlorine atom in the 9-position in Formula II. Also claimed per se are (i) the non-phytotoxic acid addition salts of compounds of formulµ I and II and (ii) the compounds, lilolidine-2-thione, lilolidine-4-thione and julolidine-3-thione. The present pyrrolo-[3,2,1-i, j]-quinolines and pyrido-[3,2,1-i, j]-quinolines (i.e. benzo[i, j]- quinolizines) are prepared by (a) reacting an appropriately substituted indole or quinoline with a chloro-substituted acid chloride in the presence of a base to form a compound of formula which is then cyclized in the presence of AlCl 3 ; (2) reacting an appropriately substituted quinoline with acrylonitrile or a #-halopropionitrile to form a compound of formula which is hydrolysed and then cyclized in the presence of a dehydrating agent (e.g. P 2 O 5 ); (3) reacting an aniline derivative with 2 moles of acrylonitrile or a #-halopropionitrile to from a compound of formula which is then hydrolysed and cyclized as in (2); (4) reacting an appropriately substituted indole or quinoline with a keto ester, (R<SP>5</SP> = C 1-4 alkyl or phenyl, R<SP>6</SP> = H or C 1-4 alkyl) to form a compound of formula which is then cyclized in the presence of a dehydrating agent (e.g. CH 2 SO 4 or polyphosphoric acid); (5) reacting an appropriately substituted indole or quinoline with a malonic acid ester, CR<SP>7</SP>R<SP>8</SP>(CO 2 C 2 H 5 ) 2 (R<SP>7</SP> and R<SP>8</SP> are each H, C 1-4 alkyl or phenyl) to form a compound of formula and (6) conversion of existing substituents in compounds of Formulµ I and II to desired substituents, e.g. oxo to hydrogen by LiAlH 4 , oxo to thioxo by P 2 S 5 , saturation of unsaturated groups and/or replacement of halogen atoms by hydrogen atoms using catalytic hydrogenation, R = H to R = halogen, alkyl, alkanoyl or benzoyl by nuclear aromatic substitutions, halogen to cyano by cuprous cyanide, a gemdihalo group to an oxo group by hydrolysis, hydroxyl to alkanoyloxy by esterification and hydroxyl to halogen by phosphorus halides or thionyl halides. The examples describe the preparation of many specific compounds of the invention which are used in plant protection. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-0139584-A2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4251659-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-102285983-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-0139584-A3 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-102285983-B http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4218448-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4833255-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/FR-2414046-A2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4886887-A |
| priorityDate | 1972-05-17-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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