GB1491863A - 2,5-or 2,6-disubstituted benzoxazoles - Google Patents

2,5-or 2,6-disubstituted benzoxazoles

Info

Publication number
GB1491863A
GB1491863A GB49260/73A GB4926073A GB1491863A GB 1491863 A GB1491863 A GB 1491863A GB 49260/73 A GB49260/73 A GB 49260/73A GB 4926073 A GB4926073 A GB 4926073A GB 1491863 A GB1491863 A GB 1491863A
Authority
GB
United Kingdom
Prior art keywords
group
convert
alkyl
reacting
hydrogen
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
GB49260/73A
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.)
Lilly Industries Ltd
Original Assignee
Lilly Industries 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 Lilly Industries Ltd filed Critical Lilly Industries Ltd
Priority to GB49260/73A priority Critical patent/GB1491863A/en
Priority to AR256198A priority patent/AR207232A1/en
Priority to ZA00746341A priority patent/ZA746341B/en
Priority to IL45837A priority patent/IL45837A/en
Priority to CS747094A priority patent/CS188927B2/en
Priority to AU74546/74A priority patent/AU486943B2/en
Priority to BG7428005A priority patent/BG26197A3/xx
Priority to AT849374A priority patent/AT341519B/en
Priority to RO7480290A priority patent/RO72841A/en
Priority to CH1414374A priority patent/CH605863A5/xx
Priority to NL7413788A priority patent/NL7413788A/en
Priority to DE19742450042 priority patent/DE2450042A1/en
Priority to DK552774A priority patent/DK552774A/da
Priority to IE2168/74A priority patent/IE40080B1/en
Priority to HULI265A priority patent/HU170452B/hu
Priority to BE6044793A priority patent/BE821350A/en
Priority to FR7435407A priority patent/FR2248039B1/fr
Priority to CA212,029A priority patent/CA1038393A/en
Priority to SU7402074061A priority patent/SU577992A3/en
Priority to DD181873A priority patent/DD114609A5/xx
Priority to ES431299A priority patent/ES431299A1/en
Priority to PL1974175042A priority patent/PL94057B1/pl
Priority to SE7413352A priority patent/SE7413352L/xx
Priority to JP49122355A priority patent/JPS5070362A/ja
Priority to AR259897A priority patent/AR207369A1/en
Priority to US05/655,668 priority patent/US4025637A/en
Publication of GB1491863A publication Critical patent/GB1491863A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2

Abstract

1491863 Benzoxazoles LILLY INDUSTRIES Ltd 22 Oct 1974 [23 Oct 1973] 49260/73 Heading C2C [Also in Division A5] Novel benzoxazoles of the general formula wherein the -CR<SP>1</SP>R<SP>2</SP>R<SP>3</SP> group is in the 5- or 6- position of the benzoxazole nucleus, R<SP>1</SP> is a hydrogen or halogen atom or a C 1-6 alkyl group, R<SP>2</SP> is a hydrogen or halogen atom or a C 1-6 alkyl, hydroxy, C 1-6 alkoxy, C 2-7 acyloxy or NR<SP>11</SP>R<SP>12</SP> group, in which R<SP>11</SP> is a hydrogen atom or C 1-6 alkyl group and R<SP>12</SP> is a hydrogen atom or C 1-6 alkyl or C 2-7 acyl group, R<SP>3</SP> is a carboxy group or a salt, ester, amide or hydroxamic acid derivative thereof or a 5-tetrazolyl or 4-R<SP>13</SP>- 4-R<SP>14</SP>-2-oxazolinyl group, in which each of R<SP>13</SP> and R<SP>14</SP> is a hydrogen atom or C 1-6 alkyl or C 1-6 hydroxyalkyl group, R<SP>4</SP> is a phenyl group optionally substituted by at least one C 1-6 alkylsulphonyl, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 haloalkyl, C 2-7 acyl, nitro, amino, hydroxy or halogen radical or in two adjacent positions by a methylene- or ethylene-dioxy group and A is CH 2 , CO or CHOR, in which R is a hydrogen atom or C 1-6 alkyl or C 2-7 acyl group, are prepared by cyclizing an o-aminophenol of the general formula wherein Z is R<SP>3</SP>, a hydrogen or halogen atom or a nitrile group, in the presence of a cyolizing agent of the formula R<SP>4</SP>-A-COOH, (R<SP>4</SP>-A-CO) 2 O, R<SP>4</SP>-A-COCl, R<SP>4</SP>-A-CONH 2 , R<SP>4</SP>-A-CONHNH 2 , R<SP>4</SP>-A-CN or R<SP>4</SP>-A-CHO and, where necessary, converting Z to R<SP>3</SP> by halogenating to convert hydrogen to halogen, by reacting with an alkali metal cyanide to convert halogen to a nitrile group, by hydrolysing to convert a nitrile group to a carbamoyl group, by hydrolysing to convert a nitrile or carbamoyl group to a carboxy group, by reacting with an alcohol under acidic conditions to convert a nitrile group to an esterified carboxy group, and optionally reacting an esterified carboxy group with hydroxylamine to convert the esterified carboxy group to a hydroxamic acid derivative, by reacting with ammonium azide to convert a nitrile group to a 5-tetrazolyl group, or optionally by reacting with an amino alcohol of formula H 2 N-CR<SP>13</SP>R<SP>14</SP>-CH 2 OH to convert a carboxy group to a 4-R<SP>13</SP>-4-R<SP>14</SP>-2-oxazolinyl group. The corresponding nitriles (R<SP>3</SP> is a cyano group) are prepared in the same way. 2,6-Dichlorophenylacetyl chloride is prepared by treating the corresponding free acid with thionyl chloride. 2-(3-Phenylacetamido-4-hydroxy phenyl) propionitrile is prepared by reacting 2-(3-amino-4-hydroxyphenyl) propionitrile with phenylacetyl chloride.
GB49260/73A 1973-10-22 1973-10-23 2,5-or 2,6-disubstituted benzoxazoles Expired GB1491863A (en)

Priority Applications (26)

Application Number Priority Date Filing Date Title
GB49260/73A GB1491863A (en) 1973-10-23 1973-10-23 2,5-or 2,6-disubstituted benzoxazoles
AR256198A AR207232A1 (en) 1973-10-23 1974-01-01 PROCEDURE TO PREPARE A BENZOXAZOLIC DERIVATIVE
ZA00746341A ZA746341B (en) 1973-10-23 1974-10-04 2,5 and 2,6 disubstituted benzoxazoles
IL45837A IL45837A (en) 1973-10-23 1974-10-11 Alpha-(2-substituted-5(or 6)-benzoxazolyl)alkanoic acid derivatives their preparation and pharmaceutical compositions containing them
CS747094A CS188927B2 (en) 1973-10-23 1974-10-16 Method of producing derivatives of 2-benzyl benzoxale
AU74546/74A AU486943B2 (en) 1973-10-23 1974-10-21 2, 5 or 2, 6-disubstituted benzoxazoles
BG7428005A BG26197A3 (en) 1973-10-23 1974-10-21
AT849374A AT341519B (en) 1973-10-23 1974-10-22 METHOD FOR PRODUCING NEW BENZOXAZOLE DERIVATIVES
RO7480290A RO72841A (en) 1973-10-23 1974-10-22 PROCEDURE FOR PREPARING BENZOXAZOL DERIVATIVES
CH1414374A CH605863A5 (en) 1973-10-23 1974-10-22
NL7413788A NL7413788A (en) 1973-10-23 1974-10-22 PROCESS FOR THE PREPARATION OF BIOLOGICALLY ACTIVE BENZOXAZOLES, PROCESS FOR THE PREPARATION OF A PREPARED MEDICINAL PRODUCT AND SUCH MEDICINAL PRODUCT.
DE19742450042 DE2450042A1 (en) 1973-10-23 1974-10-22 NEW BENZOXAZOLE DERIVATIVES AND THE PROCESS FOR THEIR PRODUCTION
DK552774A DK552774A (en) 1973-10-23 1974-10-22
IE2168/74A IE40080B1 (en) 1973-10-23 1974-10-22 2,5- or 2,6-disubstituted benzoxazoles
HULI265A HU170452B (en) 1973-10-23 1974-10-22
BE6044793A BE821350A (en) 1973-10-23 1974-10-22 DERIVATIVES OF BENZOXAZOLE SUBSTITUTION 2
FR7435407A FR2248039B1 (en) 1973-10-23 1974-10-22
CA212,029A CA1038393A (en) 1973-10-23 1974-10-22 2,5 or 2,6 disubstituted benzoxazoles
SU7402074061A SU577992A3 (en) 1973-10-23 1974-10-22 Method of preparing benzoxazole derivatives
DD181873A DD114609A5 (en) 1973-10-23 1974-10-23
ES431299A ES431299A1 (en) 1973-10-22 1974-10-23 A procedure for preparing a benzoxazole derivative. (Machine-translation by Google Translate, not legally binding)
PL1974175042A PL94057B1 (en) 1973-10-23 1974-10-23
SE7413352A SE7413352L (en) 1973-10-23 1974-10-23
JP49122355A JPS5070362A (en) 1973-10-23 1974-10-23
AR259897A AR207369A1 (en) 1973-10-23 1975-01-01 AN INTERMEDIATE PRODUCT WHICH IS A BENZOXASOL DERIVATIVE USEFUL FOR THE PREPARATION OF BENZOXAZOLES
US05/655,668 US4025637A (en) 1973-10-23 1976-02-04 2,5 OR 2,6 Disubstituted benzoxazoles

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB49260/73A GB1491863A (en) 1973-10-23 1973-10-23 2,5-or 2,6-disubstituted benzoxazoles

Publications (1)

Publication Number Publication Date
GB1491863A true GB1491863A (en) 1977-11-16

Family

ID=10451725

Family Applications (1)

Application Number Title Priority Date Filing Date
GB49260/73A Expired GB1491863A (en) 1973-10-22 1973-10-23 2,5-or 2,6-disubstituted benzoxazoles

Country Status (22)

Country Link
JP (1) JPS5070362A (en)
AR (2) AR207232A1 (en)
AT (1) AT341519B (en)
BE (1) BE821350A (en)
BG (1) BG26197A3 (en)
CA (1) CA1038393A (en)
CH (1) CH605863A5 (en)
CS (1) CS188927B2 (en)
DD (1) DD114609A5 (en)
DE (1) DE2450042A1 (en)
DK (1) DK552774A (en)
FR (1) FR2248039B1 (en)
GB (1) GB1491863A (en)
HU (1) HU170452B (en)
IE (1) IE40080B1 (en)
IL (1) IL45837A (en)
NL (1) NL7413788A (en)
PL (1) PL94057B1 (en)
RO (1) RO72841A (en)
SE (1) SE7413352L (en)
SU (1) SU577992A3 (en)
ZA (1) ZA746341B (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1435721A (en) * 1972-05-18 1976-05-12 Lilly Industries Ltd Benzoxazole derivatives
US3888864A (en) 1973-06-29 1975-06-10 Hoffmann La Roche Amino lower alkyl ether derivatives of opium alkaloids
IT1099589B (en) * 1978-08-04 1985-09-18 Ravizza Spa PROCESS FOR THE PREPARATION OF PROPIONIC BENZOXAZOLYL ACID DERIVATIVES
IT1157295B (en) * 1982-07-19 1987-02-11 Ravizza Spa PROCESS PERFECTED FOR THE PREPARATION OF DERIVATIVES OF BENZOXAZOLYL PROPIONIC ACID
JPH03173874A (en) * 1989-09-29 1991-07-29 Mitsubishi Kasei Corp New heterocyclic compound
DE102006021878A1 (en) * 2006-05-11 2007-11-15 Sanofi-Aventis Phenylamino-benzoxazole substituted carboxylic acids, process for their preparation and their use as medicaments

Also Published As

Publication number Publication date
CA1038393A (en) 1978-09-12
IL45837A0 (en) 1974-12-31
RO72841A (en) 1982-05-10
CS188927B2 (en) 1979-03-30
ATA849374A (en) 1977-06-15
HU170452B (en) 1977-06-28
FR2248039B1 (en) 1978-07-28
JPS5070362A (en) 1975-06-11
DD114609A5 (en) 1975-08-12
SE7413352L (en) 1975-04-24
IE40080B1 (en) 1979-03-14
DE2450042A1 (en) 1975-04-24
AR207232A1 (en) 1976-09-22
AU7454674A (en) 1976-04-29
NL7413788A (en) 1975-04-25
DK552774A (en) 1975-06-16
PL94057B1 (en) 1977-07-30
BE821350A (en) 1975-04-22
FR2248039A1 (en) 1975-05-16
AR207369A1 (en) 1976-09-30
AT341519B (en) 1978-02-10
SU577992A3 (en) 1977-10-25
ZA746341B (en) 1976-06-30
CH605863A5 (en) 1978-10-13
IE40080L (en) 1975-04-23
IL45837A (en) 1978-03-10
BG26197A3 (en) 1979-02-15

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee