IE40080L - 2,5- or 2,6- substituted benzoxazoles. - Google Patents
2,5- or 2,6- substituted benzoxazoles.Info
- Publication number
- IE40080L IE40080L IE742168A IE216874A IE40080L IE 40080 L IE40080 L IE 40080L IE 742168 A IE742168 A IE 742168A IE 216874 A IE216874 A IE 216874A IE 40080 L IE40080 L IE 40080L
- Authority
- IE
- Ireland
- Prior art keywords
- group
- convert
- alkyl
- reacting
- hydrogen
- Prior art date
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
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.
[GB1491863A]
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 (2)
| Publication Number | Publication Date |
|---|---|
| IE40080L true IE40080L (en) | 1975-04-23 |
| IE40080B1 IE40080B1 (en) | 1979-03-14 |
Family
ID=10451725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2168/74A IE40080B1 (en) | 1973-10-23 | 1974-10-22 | 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)
| 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 |
-
1973
- 1973-10-23 GB GB49260/73A patent/GB1491863A/en not_active Expired
-
1974
- 1974-01-01 AR AR256198A patent/AR207232A1/en active
- 1974-10-04 ZA ZA00746341A patent/ZA746341B/en unknown
- 1974-10-11 IL IL45837A patent/IL45837A/en unknown
- 1974-10-16 CS CS747094A patent/CS188927B2/en unknown
- 1974-10-21 BG BG7428005A patent/BG26197A3/xx unknown
- 1974-10-22 CH CH1414374A patent/CH605863A5/xx not_active IP Right Cessation
- 1974-10-22 DK DK552774A patent/DK552774A/da unknown
- 1974-10-22 IE IE2168/74A patent/IE40080B1/en unknown
- 1974-10-22 CA CA212,029A patent/CA1038393A/en not_active Expired
- 1974-10-22 FR FR7435407A patent/FR2248039B1/fr not_active Expired
- 1974-10-22 NL NL7413788A patent/NL7413788A/en not_active Application Discontinuation
- 1974-10-22 AT AT849374A patent/AT341519B/en not_active IP Right Cessation
- 1974-10-22 HU HULI265A patent/HU170452B/hu unknown
- 1974-10-22 DE DE19742450042 patent/DE2450042A1/en not_active Withdrawn
- 1974-10-22 BE BE6044793A patent/BE821350A/en unknown
- 1974-10-22 RO RO7480290A patent/RO72841A/en unknown
- 1974-10-22 SU SU7402074061A patent/SU577992A3/en active
- 1974-10-23 PL PL1974175042A patent/PL94057B1/pl unknown
- 1974-10-23 JP JP49122355A patent/JPS5070362A/ja active Pending
- 1974-10-23 DD DD181873A patent/DD114609A5/xx unknown
- 1974-10-23 SE SE7413352A patent/SE7413352L/xx unknown
-
1975
- 1975-01-01 AR AR259897A patent/AR207369A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| IE40080B1 (en) | 1979-03-14 |
| RO72841A (en) | 1982-05-10 |
| AU7454674A (en) | 1976-04-29 |
| CA1038393A (en) | 1978-09-12 |
| AR207232A1 (en) | 1976-09-22 |
| FR2248039A1 (en) | 1975-05-16 |
| NL7413788A (en) | 1975-04-25 |
| IL45837A (en) | 1978-03-10 |
| AT341519B (en) | 1978-02-10 |
| PL94057B1 (en) | 1977-07-30 |
| CS188927B2 (en) | 1979-03-30 |
| BE821350A (en) | 1975-04-22 |
| DE2450042A1 (en) | 1975-04-24 |
| DD114609A5 (en) | 1975-08-12 |
| GB1491863A (en) | 1977-11-16 |
| JPS5070362A (en) | 1975-06-11 |
| CH605863A5 (en) | 1978-10-13 |
| ZA746341B (en) | 1976-06-30 |
| ATA849374A (en) | 1977-06-15 |
| SE7413352L (en) | 1975-04-24 |
| IL45837A0 (en) | 1974-12-31 |
| AR207369A1 (en) | 1976-09-30 |
| BG26197A3 (en) | 1979-02-15 |
| SU577992A3 (en) | 1977-10-25 |
| DK552774A (en) | 1975-06-16 |
| HU170452B (en) | 1977-06-28 |
| FR2248039B1 (en) | 1978-07-28 |
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