GB855115A - Improvements in or relating to ª‰-aminoalkylthianaphthene and ª‰-aminoalkylbenzofuran derivatives - Google Patents

Improvements in or relating to ª‰-aminoalkylthianaphthene and ª‰-aminoalkylbenzofuran derivatives

Info

Publication number
GB855115A
GB855115A GB18397/59A GB1839759A GB855115A GB 855115 A GB855115 A GB 855115A GB 18397/59 A GB18397/59 A GB 18397/59A GB 1839759 A GB1839759 A GB 1839759A GB 855115 A GB855115 A GB 855115A
Authority
GB
United Kingdom
Prior art keywords
thianaphthene
substituted
compounds
alkyl
followed
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
GB18397/59A
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.)
Smith Kline and French Laboratories Ltd
Original Assignee
Smith Kline and French Laboratories 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 Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Publication of GB855115A publication Critical patent/GB855115A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention comprises compounds of the general formula: <FORM:0855115/IV(b)/1> (wherein Y is S, O, or SO2, R1 is hydrogen, hydroxy, fluorine, chlorine, bromine, nitro, trifluoromethyl, lower alkyl or lower alkoxy, in position 5 or 6, R2 is lower alkyl and Z is amino, mono lower alkylamino, di-lower alkylamino, cyclopentylamino, cyclohexylamino, N-piperidino or N-pyrrolidino) and their non-toxic acid addition salts and methods for their preparation. The general method involves condensation of a 2- or 3-halomethyl-R1-substituted benzofuran or thianaphthene with a diethyl a -alkyl malonate, hydrolysis of the resulting diethyl a -alkyl-a -thianaphthyl (or benzofuryl) methyl malonate, decarboxylation to the corresponding propionic acid derivative, conversion via the acid chloride and azide to the corresponding isocyanate followed (a) by heating with concentrated H Cl to yield the b -aminoalkyl thianaphthene or benzofuran, or (b) by reduction with lithium aluminium hydride to yield the analogous b -methylaminoalkyl compounds. The amino compounds are alkylated if desired by conventional methods. The S-dioxides are obtained by treatment with excess hydrogen peroxide, protecting primary amino groups by acetylation prior to oxidation. Detailed examples are given. The 3-halomethylthianaphthene intermediates are prepared from R1 substituted thiophenols by condensation with chloroacetone, cyclization and halogenation of the resulting 3-methyl-R1-substituted thianaphthene. The corresponding 2-halomethyl compounds are formed from the R1-substituted thianaphthene by treatment with butyl lithium and then formaldehyde followed by reaction of the 2-hydroxymethylthianaphthene with a halogenating agent. The 3-halomethylbenzofuran intermediates are prepared by bromination of 3-methylbenzofuran followed by debromination of the 2-bromo-3-bromomethylbenzofuran at position 2 preferably at a later stage of the synthesis. The analogous 2-halomethylbenzofurans are formed by reduction of a coumarilic acid and then halogenation of the 2-hydroxymethylbenzofurans so obtained.
GB18397/59A 1958-07-11 1959-05-29 Improvements in or relating to ª‰-aminoalkylthianaphthene and ª‰-aminoalkylbenzofuran derivatives Expired GB855115A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US855115XA 1958-07-11 1958-07-11

Publications (1)

Publication Number Publication Date
GB855115A true GB855115A (en) 1960-11-30

Family

ID=22192095

Family Applications (1)

Application Number Title Priority Date Filing Date
GB18397/59A Expired GB855115A (en) 1958-07-11 1959-05-29 Improvements in or relating to ª‰-aminoalkylthianaphthene and ª‰-aminoalkylbenzofuran derivatives

Country Status (1)

Country Link
GB (1) GB855115A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1181715B (en) * 1961-11-03 1964-11-19 Byk Gulden Lomberg Chem Fab Process for the preparation of 3- (ª ‰ -amino-ethyl) -5-methoxy-coumarone hydrochloride
DE1203276B (en) * 1961-11-03 1965-10-21 Byk Gulden Lomberg Chem Fab Process for the preparation of N-substituted 3- (beta-aminoaethyl) -coumarones
FR2092731A1 (en) * 1970-06-12 1972-01-28 Innothera Lab Sa
WO1999007667A1 (en) * 1997-08-07 1999-02-18 Fujimoto Brothers Co., Ltd. Novel ethylamine derivatives

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1181715B (en) * 1961-11-03 1964-11-19 Byk Gulden Lomberg Chem Fab Process for the preparation of 3- (ª ‰ -amino-ethyl) -5-methoxy-coumarone hydrochloride
DE1203276B (en) * 1961-11-03 1965-10-21 Byk Gulden Lomberg Chem Fab Process for the preparation of N-substituted 3- (beta-aminoaethyl) -coumarones
FR2092731A1 (en) * 1970-06-12 1972-01-28 Innothera Lab Sa
WO1999007667A1 (en) * 1997-08-07 1999-02-18 Fujimoto Brothers Co., Ltd. Novel ethylamine derivatives

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