GB762187A - Metal complexes of hydrazide-hydrazones and process for producing the same - Google Patents

Metal complexes of hydrazide-hydrazones and process for producing the same

Info

Publication number
GB762187A
GB762187A GB27854/53A GB2785453A GB762187A GB 762187 A GB762187 A GB 762187A GB 27854/53 A GB27854/53 A GB 27854/53A GB 2785453 A GB2785453 A GB 2785453A GB 762187 A GB762187 A GB 762187A
Authority
GB
United Kingdom
Prior art keywords
hydrazone
complex
chloride
hydrazide
aldehyde
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
GB27854/53A
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB762187A publication Critical patent/GB762187A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/86—Hydrazides; Thio or imino analogues thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)

Abstract

The invention comprises metal complexes of hydrazones of hydrazides of heterocyclic carboxylic acids, the metals being of the fourth Period and Groups 2 to 8 of the Periodic Table. Suitable metals are iron, cobalt, zinc, manganese, vanadium and nickel. The complexes are prepared by reacting a compound of the metal, e.g. a salt, with the hydrazone, in water or other solvent such as alcohol. The heterocyclic acid radical may be derived from nicotinic, isonicotinic, alkylisonicotinic, pyromucic, and quinoline, thiophene, pyrazole and pyrimidine carboxylic acids. Particularly useful products are obtained when the hydrazone is derived from an aldehyde or ketone which bears in the 2-position to the oxo group a substituent capable of participating in the complex formation. Examples of such aldehydes and ketones are o-hydroxybenzaldehyde and its derivatives, e.g. the 3,5-dichloro- and 6-nitro-derivatives, 2-naphthol-1-aldehyde, o-amino-benzaldehyde, pyridine-2-aldehyde, pyrrole-2-aldehyde, furfural, resorcylaldehyde, phthalaldehyde acid, p-chloro-phenyl glyoxal, resacetophenone, o-quinones, glycol aldehyde, dextrose, glyceryl aldehyde, glyoxalic acid and diacetylmonoxime and bilateral reaction products of such o-dioxo compounds as glyoxal and diacetyl with the hydrazides. In the examples: (1) the compound <FORM:0762187/IV(b)/1> is obtained from ferric ammonium sulphate and o-hydroxy-benzalisonicotinic acid hydrazide hydrazone; (2) (a) the chloride salt is obtained starting from ferric chloride, (b) the corresponding complex is obtained from ferric chloride and fural-isonicotinic acid hydrazide-hydrazone; (3) the compound having the approximate formula <FORM:0762187/IV(b)/2> is obtained from iron butylate and o-hydroxybenzalisonicotinic acid hydrazide-hydrazone. Analogous results are obtained using iron acetyl acetonate or other non-ionic metal compounds; (4) the same hydrazone as in (3) is reacted with cobaltous chloride to form a complex; (5) using the same hydrazone and manganese chloride, a complex is obtained which contains 2 chlorine atoms to 1 molecule of hydrazone and which on boiling yields a complex of lower chlorine content; (6) the compound of the formula <FORM:0762187/IV(b)/3> is prepared from ammonium vanadate and the same hydrazone as in (1); (7) a complex is obtained from ferric chloride and o-hydroxypyromucic acid hydrazide-hydrazone; (8) the hydrazone used in (1) is reacted with zinc chloride to give a complex containing 4 mols. of hydrazone to 3 mols. of zinc chloride; (9) nickelous chloride is reacted with (a) the hydrazone of isonicotinyl hydrazide and 2-hydroxynaphthaldehyde-1, (b) the hydrazone used in (1), (c) the hydrazone of o-hydroxypyromucic acid hydrazide; (10) a bivalent iron complex is prepared from iron chloride and benzal-isonicotinyl hydrazide hydrazone; (11) the bilateral reaction product of diacetyl and isonicotinyl hydrazide is refluxed with iron chloride to give a soluble complex; (12) ferric chloride is reacted with the isonicotinyl hydrazide-hydrazone of (a) resorcaldehyde, (b) 2-hydroxy-3-methoxy-benzaldehyde, and (c) 2-hydroxy-4-methoxy benzaldehyde. Also specified is the complex <FORM:0762187/IV(b)/4> prepared from the hydrazone <FORM:0762187/IV(b)/5> which is obtained from 2,4-dihydroxyacetophenone; and the complex <FORM:0762187/IV(b)/6> prepared from the hydrazone <FORM:0762187/IV(b)/7> which is obtained from 2-hydroxy-4-methoxy benzaldehyde.
GB27854/53A 1952-10-09 1953-10-09 Metal complexes of hydrazide-hydrazones and process for producing the same Expired GB762187A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE762187X 1952-10-09

Publications (1)

Publication Number Publication Date
GB762187A true GB762187A (en) 1956-11-28

Family

ID=6667226

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27854/53A Expired GB762187A (en) 1952-10-09 1953-10-09 Metal complexes of hydrazide-hydrazones and process for producing the same

Country Status (1)

Country Link
GB (1) GB762187A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007519691A (en) * 2004-01-30 2007-07-19 クリニジェネティクス Hydrazide-type compounds and use of the compounds in pharmaceutical compositions for the treatment of cardiovascular diseases
CN109553642A (en) * 2018-12-18 2019-04-02 南京林业大学 The preparation method and use of o-vanillin isonicotinoyl hydrazone iron and nickel complex
CN110759833A (en) * 2019-10-25 2020-02-07 国家林业和草原局竹子研究开发中心 Preparation method and application of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007519691A (en) * 2004-01-30 2007-07-19 クリニジェネティクス Hydrazide-type compounds and use of the compounds in pharmaceutical compositions for the treatment of cardiovascular diseases
CN109553642A (en) * 2018-12-18 2019-04-02 南京林业大学 The preparation method and use of o-vanillin isonicotinoyl hydrazone iron and nickel complex
CN109553642B (en) * 2018-12-18 2021-02-02 南京林业大学 Synthesis method and application of o-vanillin iso-nicotinyl hydrazone iron and nickel complex
CN110759833A (en) * 2019-10-25 2020-02-07 国家林业和草原局竹子研究开发中心 Preparation method and application of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide
CN110759833B (en) * 2019-10-25 2022-06-14 国家林业和草原局竹子研究开发中心 Preparation method and application of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide

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