GB1364917A - Preparation of 1h-tetrazole compounds - Google Patents
Preparation of 1h-tetrazole compoundsInfo
- Publication number
- GB1364917A GB1364917A GB4419971A GB4419971A GB1364917A GB 1364917 A GB1364917 A GB 1364917A GB 4419971 A GB4419971 A GB 4419971A GB 4419971 A GB4419971 A GB 4419971A GB 1364917 A GB1364917 A GB 1364917A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- formula
- tetrazoles
- alkyl group
- phenyl
- 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
Links
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical class C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 title abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- -1 biphenylyl Chemical group 0.000 abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 abstract 1
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical class N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003536 tetrazoles Chemical class 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- 125000005023 xylyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1364917 1 H-Tetrazoles FUJISAWA PHARMACEUTICAL CO Ltd 22 Sept 1971 44199/71 Heading C2C 1H-Tetrazoles of Formula I: wherein each of R and R<SP>1</SP> is hydrogen; or an unsubstituted C 1-6 alkyl group; a phenyl, tolyl, xylyl, mesityl, naphthyl, biphenylyl, benzyl, tolylmethyl, xylylmethyl, phenethyl, tolylethy, α-methylbenzyl or α-methylphenethyl group; or a C 1-6 alkyl group substituted by a halogen atom or by a carboxyl, C 2-7 alkoxycarbonyl, benzyloxycarbonyl, tolylmethyloxycarbonyl, xylylmethoxycarbonyl, phenethoxycarbonyl, tolylethoxycarbonyl, α - methylbenzyloxycarbonyl, α - methylphenethoxycarbonyl, carbamoyl, hydroxy, amino, methylamino, ethylamino, propylamino, isopropylamino, dimethylamino, diethylamino, dipropylamino, methylethylamino, or C 1-4 alkoxy group, are prepared by reacting a compound of formula RNH 2 , or a salt thereof with a hydrazoic acid salt and an orthocarboxylic acid ester of formula R<SP>1</SP>C(OR<SP>2</SP>) 3 , wherein R<SP>2</SP> is a C 1-6 alkyl group. The reaction is preferably carried out in a solvent inert under the reaction conditions, e.g. acetic acid, propionic acid, an alcohol or dimethylformamide, and with heating. The examples prepare tetrazoles of Formula I wherein R and R<SP>1</SP> are respectively, phenyl and hydrogen, hydrogen and hydrogen, -CH 2 CO 2 H and -CH 3 , -CH 2 CO 2 H and hydrogen, -CH 2 CO 2 C 2 H 5 and hydrogen, and -C(CH 3 ) 2 - CH 2 OH and hydrogen.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4419971A GB1364917A (en) | 1971-09-22 | 1971-09-22 | Preparation of 1h-tetrazole compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4419971A GB1364917A (en) | 1971-09-22 | 1971-09-22 | Preparation of 1h-tetrazole compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1364917A true GB1364917A (en) | 1974-08-29 |
Family
ID=10432215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4419971A Expired GB1364917A (en) | 1971-09-22 | 1971-09-22 | Preparation of 1h-tetrazole compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1364917A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036849A (en) * | 1974-05-15 | 1977-07-19 | American Cyanamid Company | 1-(Para-substituted-phenyl)-1H-tetrazoles |
| FR2517676A1 (en) * | 1981-12-07 | 1983-06-10 | Delalande Sa | NOVEL TETRAZOLIC DERIVATIVES SUBSTITUTED IN POSITION 5, PROCESS FOR PREPARING THEM AND THEIR THERAPEUTIC USE |
| WO1999023080A1 (en) * | 1997-11-04 | 1999-05-14 | Uniroyal Chemical Company, Inc. | Pesticidal tetrazole derivatives |
| RU2470925C1 (en) * | 2011-11-01 | 2012-12-27 | Закрытое акционерное общество "Новая бытовая химия" | Method of producing 1-c1-6alkyl- and 1-phenyl-5-iodotetrazoles |
-
1971
- 1971-09-22 GB GB4419971A patent/GB1364917A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036849A (en) * | 1974-05-15 | 1977-07-19 | American Cyanamid Company | 1-(Para-substituted-phenyl)-1H-tetrazoles |
| FR2517676A1 (en) * | 1981-12-07 | 1983-06-10 | Delalande Sa | NOVEL TETRAZOLIC DERIVATIVES SUBSTITUTED IN POSITION 5, PROCESS FOR PREPARING THEM AND THEIR THERAPEUTIC USE |
| WO1999023080A1 (en) * | 1997-11-04 | 1999-05-14 | Uniroyal Chemical Company, Inc. | Pesticidal tetrazole derivatives |
| JP3489624B2 (en) | 1997-11-04 | 2004-01-26 | ユニロイヤル ケミカル カンパニー インコーポレイテッド | Tetrazole derivatives with pest killing action |
| RU2470925C1 (en) * | 2011-11-01 | 2012-12-27 | Закрытое акционерное общество "Новая бытовая химия" | Method of producing 1-c1-6alkyl- and 1-phenyl-5-iodotetrazoles |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |