IE40080B1 - 2,5- or 2,6-disubstituted benzoxazoles - Google Patents
2,5- or 2,6-disubstituted benzoxazolesInfo
- Publication number
- IE40080B1 IE40080B1 IE2168/74A IE216874A IE40080B1 IE 40080 B1 IE40080 B1 IE 40080B1 IE 2168/74 A IE2168/74 A IE 2168/74A IE 216874 A IE216874 A IE 216874A IE 40080 B1 IE40080 B1 IE 40080B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- convert
- alkyl
- reacting
- hydrogen
- Prior art date
Links
- -1 2,6-disubstituted benzoxazoles Chemical class 0.000 title abstract 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 7
- 125000002560 nitrile group Chemical group 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000000355 1,3-benzoxazolyl group Chemical class O1C(=NC2=C1C=CC=C2)* 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 1
- VFRDBQGBQYINBH-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=C(Cl)C=CC=C1Cl VFRDBQGBQYINBH-UHFFFAOYSA-N 0.000 abstract 1
- YOCRMABISPGUSN-UHFFFAOYSA-N 2-(3-amino-4-hydroxyphenyl)propanenitrile Chemical compound N#CC(C)C1=CC=C(O)C(N)=C1 YOCRMABISPGUSN-UHFFFAOYSA-N 0.000 abstract 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- UAZDIGCOBKKMPU-UHFFFAOYSA-O azanium;azide Chemical compound [NH4+].[N-]=[N+]=[N-] UAZDIGCOBKKMPU-UHFFFAOYSA-O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- UOQQYQILJGCDCO-UHFFFAOYSA-N n-[5-(1-cyanoethyl)-2-hydroxyphenyl]-2-phenylacetamide Chemical compound N#CC(C)C1=CC=C(O)C(NC(=O)CC=2C=CC=CC=2)=C1 UOQQYQILJGCDCO-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
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 IE40080L (en) | 1975-04-23 |
| IE40080B1 true 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 BG028005A patent/BG26197A3/en unknown
- 1974-10-22 HU HULI265A patent/HU170452B/hu unknown
- 1974-10-22 AT AT849374A patent/AT341519B/en not_active IP Right Cessation
- 1974-10-22 BE BE6044793A patent/BE821350A/en unknown
- 1974-10-22 DK DK552774A patent/DK552774A/da unknown
- 1974-10-22 NL NL7413788A patent/NL7413788A/en not_active Application Discontinuation
- 1974-10-22 RO RO7480290A patent/RO72841A/en unknown
- 1974-10-22 CA CA212,029A patent/CA1038393A/en not_active Expired
- 1974-10-22 CH CH1414374A patent/CH605863A5/xx not_active IP Right Cessation
- 1974-10-22 IE IE2168/74A patent/IE40080B1/en unknown
- 1974-10-22 FR FR7435407A patent/FR2248039B1/fr not_active Expired
- 1974-10-22 DE DE19742450042 patent/DE2450042A1/en not_active Withdrawn
- 1974-10-22 SU SU7402074061A patent/SU577992A3/en active
- 1974-10-23 DD DD181873A patent/DD114609A5/xx unknown
- 1974-10-23 PL PL1974175042A patent/PL94057B1/pl unknown
- 1974-10-23 JP JP49122355A patent/JPS5070362A/ja active Pending
- 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 |
|---|---|
| CS188927B2 (en) | 1979-03-30 |
| SU577992A3 (en) | 1977-10-25 |
| DK552774A (en) | 1975-06-16 |
| RO72841A (en) | 1982-05-10 |
| NL7413788A (en) | 1975-04-25 |
| JPS5070362A (en) | 1975-06-11 |
| BG26197A3 (en) | 1979-02-15 |
| SE7413352L (en) | 1975-04-24 |
| AR207232A1 (en) | 1976-09-22 |
| GB1491863A (en) | 1977-11-16 |
| CH605863A5 (en) | 1978-10-13 |
| AU7454674A (en) | 1976-04-29 |
| PL94057B1 (en) | 1977-07-30 |
| IE40080L (en) | 1975-04-23 |
| DE2450042A1 (en) | 1975-04-24 |
| BE821350A (en) | 1975-04-22 |
| AT341519B (en) | 1978-02-10 |
| AR207369A1 (en) | 1976-09-30 |
| ZA746341B (en) | 1976-06-30 |
| FR2248039B1 (en) | 1978-07-28 |
| IL45837A (en) | 1978-03-10 |
| HU170452B (en) | 1977-06-28 |
| IL45837A0 (en) | 1974-12-31 |
| CA1038393A (en) | 1978-09-12 |
| FR2248039A1 (en) | 1975-05-16 |
| ATA849374A (en) | 1977-06-15 |
| DD114609A5 (en) | 1975-08-12 |
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