GB711756A - Novel heterocyclic compounds and process for the manufacture thereof - Google Patents
Novel heterocyclic compounds and process for the manufacture thereofInfo
- Publication number
- GB711756A GB711756A GB22274/52A GB2227452A GB711756A GB 711756 A GB711756 A GB 711756A GB 22274/52 A GB22274/52 A GB 22274/52A GB 2227452 A GB2227452 A GB 2227452A GB 711756 A GB711756 A GB 711756A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrazino
- hydrazine
- dichloro
- pyridyl
- diethoxy
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0711756/IV (b)/1> wherein Y and Y1 both stand for hydrogen or halogen atoms or for alkoxy groups, R2 stands for a hydrogen atom and R3 stands for a heterocyclic radical or R2 and R3, together with the nitrogen atom to which they are attached, form a heterocyclic ring which, when Y and Y1 both stand for hydrogen, is other than a saturated six-membered ring, or, where the fragment -NH-N(R2)R3 contains the group <FORM:0711756/IV (b)/2> triazolo compounds derived therefrom by loss of the elements of water and having the group <FORM:0711756/IV (b)/3> Pyridine-4-carboxylic acids or derivatives thereof of the general formula <FORM:0711756/IV (b)/4> or salts thereof, wherein X stands for a hydroxy, an alkoxy, an amino or an azido group or for a halogen atom are reacted with hydrazine derivatives of the formula <FORM:0711756/IV (b)/5> or salts thereof, preferably in presence of a basic agent such as pyridine. Pyridine carboxylic acid derivatives containing the following radicals are specified as starting materials: pyridyl-(4)-, 2,6 - dichloro - pyridyl - (4) -, 2,6 - diethoxy - pyridyl-(4)- and 2,6-dibutyloxy-pyridyl-(4)-. Acid halides are especially suitable derivatives, particularly the acid chlorides which may be employed in the form of the hydrochloride salts. Specified hydrazine derivatives are: pyridyl-(2, 3, or 4)-hydrazine, 5-nitro-2-hydrazinopyridine, 5 - amino - 2 - hydrazino - pyridine, 2 - hydrazino - thiazole, 2 - hydrazino - benzthiazole, 6 - chloro - 3 - hydrazino - pyridiazine, 6 - methyl - 3 - hydrazino - pyridazine, 1 - hydrazino - phthalazine, 2,4 - dimethyl - 6 - hydrazino-pyrimidine, 2-hydrazino-pyrazines and 2 - hydrazino - quinoxalines. Alternatively pyridine-(4)-carboxylic acid hydrazides are reacted with the appropriate heterocyclic halogen compounds. Products in which Y and Y1 are chlorine atoms may be subsequently reduced to give compounds in which Y and Y1 are hydrogen atoms. The examples describe the preparation of N1-[isonicotinoyl]-N2-[5-nitro - pyridyl - (2)] - hydrazine; N1 - [isonicotinoyl] - N2 - (5 - amino - pyridyl - (2)] - hydrazine; N - [morpholinyl - (41)] - 2,6 - dichloro-isonicotinic acid amide; N-[piperidyl-(11)]-2,6-dichloro-isonicotinic acid amide; N1-[2,6 - dichloro - isonicotinoyl] - N2 - [61 - chloro - pyridazinyl - (31)] - hydrazine; N1 - [2,6-dichloro - isonicotinoyl] - N2 - [31 - methyl - pyridazinyl - (61)] - hydrazine; N1 - [2,6 - dichloro - isonicotinoyl] - N2 - [benzthiazolyl - (21)]-hydrazine; 2,6-diethoxy-isonicotinic acid N - (morpholino) - amide; 2,6 - diethoxy - isonicotinic acid N-(piperidino)-amide; N1-[2,6-diethoxy - isonicotinoyl] - N2 - (21,41 - dimethyl - pyrimidyl - (61)] - hydrazine; 3 - [21,61 - di ethoxy - pyridyl - (41)] - triazolophthalazine; and 3 - [21,61 - dichloro - pyridyl - (41)] - triazolophthalazine. 3 - Hydrazino - 6 - chloro - pyridazine is prepared by boiling 3,6-dichloro-pyridazine with hydrazine hydrate in alcoholic solution. 2,6-Diethoxy-isonicotinic acid chloride is prepared by refluxing 2,6-diethoxy-isonicotinic acid with phosphorus pentachloride in absolute benzene. 2,6-Diethoxy-isonicotinic acid is prepared by heating 2,6-dichloro-isonicotinic acid with sodium ethoxide and treating the resulting sodium salt with hydrochloric acid.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH711756X | 1951-09-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB711756A true GB711756A (en) | 1954-07-07 |
Family
ID=4530819
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB22274/52A Expired GB711756A (en) | 1951-09-06 | 1952-09-04 | Novel heterocyclic compounds and process for the manufacture thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB711756A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4137067A (en) | 1975-05-14 | 1979-01-30 | Ciba-Geigy Corporation | Pyridine-4-carboxylic acid hydrazides for combatting phytopathogenic microorganisms and for regulating plant growth |
EP0288976A2 (en) * | 1987-04-29 | 1988-11-02 | Ciba-Geigy Ag | Protecting agent for plant diseases |
-
1952
- 1952-09-04 GB GB22274/52A patent/GB711756A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4137067A (en) | 1975-05-14 | 1979-01-30 | Ciba-Geigy Corporation | Pyridine-4-carboxylic acid hydrazides for combatting phytopathogenic microorganisms and for regulating plant growth |
EP0288976A2 (en) * | 1987-04-29 | 1988-11-02 | Ciba-Geigy Ag | Protecting agent for plant diseases |
EP0288976A3 (en) * | 1987-04-29 | 1989-11-23 | Ciba-Geigy Ag | Protecting agent for plant diseases |
US5015649A (en) * | 1987-04-29 | 1991-05-14 | Ciba-Geigy Corporation | Plant-protective compositions |
US5126358A (en) * | 1987-04-29 | 1992-06-30 | Ciba-Geigy Corporation | Plant-protective compositions |
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