GB1394374A - Pyrrolo-quinoline and pyrido-quinoline derivatives - Google Patents

Pyrrolo-quinoline and pyrido-quinoline derivatives

Info

Publication number
GB1394374A
GB1394374A GB3137674A GB3137674A GB1394374A GB 1394374 A GB1394374 A GB 1394374A GB 3137674 A GB3137674 A GB 3137674A GB 3137674 A GB3137674 A GB 3137674A GB 1394374 A GB1394374 A GB 1394374A
Authority
GB
United Kingdom
Prior art keywords
alkyl
formula
quinoline
halogen
reacting
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
GB3137674A
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.)
Pfizer Ltd
Original Assignee
Pfizer 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 Pfizer Ltd filed Critical Pfizer Ltd
Priority to GB3137674A priority Critical patent/GB1394374A/en
Publication of GB1394374A publication Critical patent/GB1394374A/en
Priority to MY7700082A priority patent/MY7700082A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine

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.
GB3137674A 1972-05-17 1972-05-17 Pyrrolo-quinoline and pyrido-quinoline derivatives Expired GB1394374A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB3137674A GB1394374A (en) 1972-05-17 1972-05-17 Pyrrolo-quinoline and pyrido-quinoline derivatives
MY7700082A MY7700082A (en) 1972-05-17 1977-12-31 Pyrrolo-quinoline and pyrido-quinoline derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3137674A GB1394374A (en) 1972-05-17 1972-05-17 Pyrrolo-quinoline and pyrido-quinoline derivatives

Publications (1)

Publication Number Publication Date
GB1394374A true GB1394374A (en) 1975-05-14

Family

ID=10322179

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3137674A Expired GB1394374A (en) 1972-05-17 1972-05-17 Pyrrolo-quinoline and pyrido-quinoline derivatives

Country Status (2)

Country Link
GB (1) GB1394374A (en)
MY (1) MY7700082A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2414046A2 (en) * 1977-12-22 1979-08-03 Du Pont Antihypertensive pyrrolo (3,2,1-i,j)-quinoline-4-one derivs. - are 8-hydroxy-fluoroalkyl-1,2-di:hydro-4H cpds. which act by peripheral vasodilation
US4218448A (en) * 1976-06-24 1980-08-19 E. I. Du Pont De Nemours And Company Antihypertensive polyfluorohydroxyisopropyl bicyclic and tricyclic carbostyrils
US4251659A (en) 1977-12-22 1981-02-17 E. I. Du Pont De Nemours And Company Polyfluorohydroxyisopropyl-heterocyclic compounds
EP0139584A2 (en) * 1983-10-17 1985-05-02 Synthelabo Imidazoline derivatives, their preparation and therapeutical use
US4833255A (en) * 1984-05-16 1989-05-23 Ciba-Geigy Corporation Process for the preparation of indoline
US4886887A (en) * 1985-11-08 1989-12-12 Ciba-Geigy Corporation Process for the preparation of indolines
CN102285983A (en) * 2010-06-21 2011-12-21 中国水产科学研究院东海水产研究所 Method for modifying flumequine into 7-hydroxyflumequine

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4218448A (en) * 1976-06-24 1980-08-19 E. I. Du Pont De Nemours And Company Antihypertensive polyfluorohydroxyisopropyl bicyclic and tricyclic carbostyrils
FR2414046A2 (en) * 1977-12-22 1979-08-03 Du Pont Antihypertensive pyrrolo (3,2,1-i,j)-quinoline-4-one derivs. - are 8-hydroxy-fluoroalkyl-1,2-di:hydro-4H cpds. which act by peripheral vasodilation
US4251659A (en) 1977-12-22 1981-02-17 E. I. Du Pont De Nemours And Company Polyfluorohydroxyisopropyl-heterocyclic compounds
EP0139584A2 (en) * 1983-10-17 1985-05-02 Synthelabo Imidazoline derivatives, their preparation and therapeutical use
EP0139584A3 (en) * 1983-10-17 1986-02-19 Synthelabo Imidazoline derivatives, their preparation and therapeutical use
US4833255A (en) * 1984-05-16 1989-05-23 Ciba-Geigy Corporation Process for the preparation of indoline
US4886887A (en) * 1985-11-08 1989-12-12 Ciba-Geigy Corporation Process for the preparation of indolines
CN102285983A (en) * 2010-06-21 2011-12-21 中国水产科学研究院东海水产研究所 Method for modifying flumequine into 7-hydroxyflumequine
CN102285983B (en) * 2010-06-21 2013-05-08 中国水产科学研究院东海水产研究所 Method for modifying flumequine into 7-hydroxyflumequine

Also Published As

Publication number Publication date
MY7700082A (en) 1977-12-31

Similar Documents

Publication Publication Date Title
GB1489280A (en) Indazole derivatives
ES430104A1 (en) Cephalosporin compounds
GB1301224A (en)
GB1382782A (en) Alkylarylketones processes for their preparation and compositions incorporating them
GB1394374A (en) Pyrrolo-quinoline and pyrido-quinoline derivatives
GB1215066A (en) Acrylamides and their use as fungicides
ES8206509A1 (en) Reactive derivatives of 3-oxa-bicyclo(4.3.0)-non-1-ene-9-one, process for their preparation and their use.
ES406081A1 (en) 4-(M-benzoylphenyl)butyric acid derivatives
ES293991A1 (en) Intermediates for and synthesis of vitamin b and related compounds
DE3372095D1 (en) Novel phenylpiperazine derivatives and process for producing the same
GB1508734A (en) 1,3-dithiolan-2-ylidene malonate derivatives and process for the preparation thereof and usage thereof
GB1495305A (en) 3-phenyl-4-oxo-4h-benzopyran derivatives
SE7613990L (en) ORATIC ACID DERIVATIVES TO PREPARE NEW 7-AMINO-T IAZOLYL-ACETAMIDO-CEPHALOSP
GB999092A (en) Method for making benzo(a)-quinolizine derivatives
GB1186495A (en) 0-[3-(4-Fluorobenzoyl) Proplyl]-4-Substituted Piperazines, their Acid Addition Salts and their method of preparation
SE7415015L (en) METHODS OF PRODUCING NEW 2-PHENYLHYDRAZINO-THIAZOLINES OR -TIAZINES
GB1390304A (en) 1,2,3,4-tetrahydro-9h-pyrido-3,4b indole derivatives and their use as intermediates in the synthesis of eburnamonine
GB1461667A (en) Amphetamine derivatives
GB1357212A (en) Benzothiophene derivatives and process for preparing the same
GB993156A (en) Quinolizine derivatives
US4226984A (en) 2-Decarboxy-2-aminomethyl-trans-4,5-didehydro-PGI1 compounds
GB1371896A (en) Hydroxyaryl amino acids
GB2012762A (en) 5,6-dihydro prostacyclin derivatives
GB1324687A (en) 3-amino-delta2-pyrazoline derivatives and process for the preparation thereof
GB1301366A (en)

Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years

Effective date: 19930514