RO105079B1 - Salicilhydrazidone new deriwates - Google Patents
Salicilhydrazidone new deriwates Download PDFInfo
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- RO105079B1 RO105079B1 RO14312189A RO14312189A RO105079B1 RO 105079 B1 RO105079 B1 RO 105079B1 RO 14312189 A RO14312189 A RO 14312189A RO 14312189 A RO14312189 A RO 14312189A RO 105079 B1 RO105079 B1 RO 105079B1
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Abstract
Invenția prezintă noi derivați de salicilhidrazidonă, cu formula generală 1 in care R este CH', iar R1 este H sau Cl. Compușii sunt obținuți prin condensarea necatalizată a hidrazidei acidului saliciiic cu compuși orro-hidroxicarboxilici. în metanol, la reflux. Compușii sc pot utiliza ca liganzi analitici dc tip ON\O ș/ po: prezenta și interes farmacologic, dalii fund existența restului dc acid saliciiic și a clorului.The invention discloses novel salicylhydrazidone derivatives, of the general formula 1 wherein R is CH 'and R1 is H or Cl. compounds are obtained by the uncatalyzed condensation of salicylic acid hydrazide with orro-hydroxycarboxylic compounds. in methanol, at reflux. Compounds sc I can use as analytical ligands dc type ON \ O and po: present and pharmacological interest, give the existence of the rest with salicylic acid and chlorine.
Description
Este cunoscută salicilhidrazidona aldehidei salicilice cu formula I, în care R = R1 = H, utilizată pentru caracterizarea analitică a unor cationi ca: Co111, Th17, LlV1, La111 și U11' și ca substanță tuberculostatică.Salicylhydrazidone is known as salicylic aldehyde of formula I, wherein R = R 1 = H, used for the analytical characterization of cations such as: Co 111 , Th 17 , L lV1 , La 111 and U 11 'and as a tuberculostatic substance.
Compușii sc obțin prin refluxarea în mediu de alcool a hidrazidei acidului respectiv cu aldcliidă, după care sc separă produsele rezultate.The compounds sc obtain by refluxing into the alcohol medium the hydrazide of the respective acid with aldcliid, after which sc separates the resulting products.
Scopul prezentei invenții este lărgirea gamei hidrazidonclor hidrazidclor acidului salicilic.The object of the present invention is to widen the range of hydrazidonclor hydrochloride of salicylic acid.
Problema pe care o rezolvă invenția este de a găsi acea asociere de materii prime care să permită realizarea scopului propus.The problem to be solved by the invention is to find that combination of raw materials that will allow to achieve the proposed purpose.
Invenția lărgește gama derivaților salieilhidrazidonelor, prin aceea că R este CH3, iar Rj este ales dintre H și Cl și sunt produse cristaline cu p.l. cuprinse între 221 și 322°C.The invention extends the range of the sallylhydrazidone derivatives, in that R is CH 3 and Rj is selected from H and Cl and are crystalline products with pl ranging from 221 to 322 ° C.
Se dau în continuare 2 exemple dc realizare a invenției.The following are two examples of the invention.
Exemplul 1. Salicilhidrazidona 2hidroxiacetofe noneiExample 1. Salicylhydrazidone 2hydroxyacetophones none
15,2 părți în greutate hidrazidă a acidului salicilic cu 10 părți în volume 2hidroxiacetofenonă în 200 părți volume metanol se refluxează timp de 2 h, se lasă în repaus 48 h la temperatura camerei, se filtrează produsul obținut, se usucă pe hârtie de filtru și se recri stal izează din dimetilformainidă, se obțin 17 părți în greutate produs cu p.l. 221 ... ... 222°C (randament 63%).15.2 parts by weight hydrazide of salicylic acid with 10 parts by volume 2hydroxyacetophenone in 200 parts volumes methanol is refluxed for 2 hours, allowed to stand for 48 hours at room temperature, filter the obtained product, dry on filter paper and recrystallize from dimethylformainide, 17 parts by weight obtained with pl 221 ... ... 222 ° C (63% yield).
Spectrul I.R. (KBr): 3400 (OH asociat prin legături intramoleculare de hidrogen), 3000 - 2950 (CH alifatic, 1675 (CO amidic), 1620 (C=N), 1380 (inel benzoic), 750 (benzen orto/disubstituit) cm'1.IR spectrum (KBr): 3400 (OH associated via intramolecular hydrogen bonds), 3000-250 (aliphatic CH, 1675 (amide CO), 1620 (C = N), 1380 (benzoic ring), 750 (ortho / disubstituted benzene) cm ' 1 .
Spectrul R.H.N (CDC13 + DMSO -d6): δ = 2,0 (s, 3H, CH3), 7,35 (m, 8H, protoni aromatici) ppm. Nu se observă nici în acest caz semnalele grupărilor OH și NH probabil datorită DMSO-ului.RHN spectrum (CDC1 3 + DMSO -d 6 ): δ = 2.0 (s, 3H, CH 3 ), 7.35 (m, 8H, aromatic protons) ppm. The signals of the OH and NH groups are probably not observed in this case, probably due to the DMSO.
Exemplul 2. Salicilhidrazidona 3; 5dicloro-2-hidroxi-acetofenonei părți în greutate hidrazidă a acidului salicilic cu 20,4 părți în greutate 3,5dicloro-2 -hidroziacetofenona în 250 părți în volume metanol sc refluxează timp de 3 h, după care se lasă în repaus la temperatura camerei timp de 48 h. Se filtrează produsul care separă, se usucă, obținânduse după recristalizarc din DNF 21 părți în greutate cu p.t. 321 ... 322°C (randament 63%).Example 2. Salicylhydrazidone 3; 5dichloro-2-hydroxy-acetophenone parts by weight hydrazide of salicylic acid with 20.4 parts by weight 3,5dichloro-2-hydroxyacetophenone in 250 parts by volume methanol sc reflux for 3 hours, then left to rest at room temperature for 48 h. Filter the separating product, dry, obtained after recrystallization from DNF 21 parts by weight with pt 321 ... 322 ° C (63% yield).
Analize: Calculat Găsit:Analyzes: Calculated Found:
%C= 53,11; 53.27 °Â H= 3,54; 3,68 % N= 8,26: 8,50 % Cl=20,92; 21,12% C, 53.11; 53.27 ° H = 3.54; 3.68% N = 8.26: 8.50% Cl = 20.92; 21.12
Spectrul I.R. (KBr.): 3400 (C.H asociat prin legături intermoleculare de hidrogen). 2900 (CH alifatic), 1675 (CO amidic), 1620 (C=N) 1595 (inel benzenic) cm'1 IR spectrum (KBr.): 3400 (CH associated by intermolecular hydrogen bonds). 2900 (aliphatic CH), 1675 (amidic CO), 1620 (C = N) 1595 (benzene ring) cm ' 1
Spectrul R.M.N. (DMSO - d„) : ό = 2,15 (s, 3H, CH3) 7,20 (m, 6H, aromatici) ppm.NMR spectrum (DMSO-d '): ό = 2.15 (s, 3H, CH 3 ) 7.20 (m, 6H, aromatic) ppm.
Reacțiile care s-au efectuat reprezintă o extindere a condensării compușilor or\ohidroxicarbonilici cu derivați organici ai hidrazinei, iar randamentele bune, precum și puritatea produșilor care se obțin justifică sinteza liganzilor organici utilizabili în chimia analitică.The reactions that have been performed represent an extension of the condensation of the hydroxycarbonyl compounds with organic hydrazine derivatives, and the good yields as well as the purity of the obtained products justify the synthesis of the organic ligands usable in analytical chemistry.
Mecanismul reacției dc obținere a compușilor conform invenției implică urmălna105079 rele faze:The mechanism of the reaction to obtain the compounds according to the invention involves the following phase 105079:
\>O :\> O:
H2N-NH-COAr ><H 2 N-NH-COAr><
KJN-NH-COAr H (+) /OH ><>' z» K JN-NH-COAr H (+) / OH><>'z »
N-NH-CO - ArN-NH-CO - Ar
-H2O >C = N-NH-CO-Ar I-H 2 O> C = N-NH-CO-Ar I
Atacul nucleofil al grupării aminice prin electronii săi neparticipanți conduce la intermediarul tetraedric bipolar (A), care, prin transfer intramolecular de pro- 5 ton, trece în (B) ce se deshidratează conducând la hidrazidona (I).The nucleophilic attack of the amine group by its non-participating electrons leads to the bipolar tetrahedral intermediate (A), which, through intramolecular transfer of proton, passes into (B) which is dehydrated leading to hydrazidone (I).
Invenția prezintă avantajul că hidrazidonele conform invenției lărgesc gama liganzilor de tip ONNO a căror capacilate 10 de chelatizare confirmă utilitatea sintezei reactivilor organici din categoria compușilor de condensare a hidrazidei de interes farmacologic cu compuși carbonilici, necesari recuperării cationilor metalelor 15 deficitare.The invention has the advantage that the hydrazidones according to the invention broaden the range of ONNO-type ligands whose chelating capacities 10 confirm the usefulness of the synthesis of organic reagents from the hydrazide condensation compounds of pharmacological interest with carbonyl compounds, necessary to recover the deficient metal cations.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RO14312189A RO105079B1 (en) | 1989-12-11 | 1989-12-11 | Salicilhydrazidone new deriwates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RO14312189A RO105079B1 (en) | 1989-12-11 | 1989-12-11 | Salicilhydrazidone new deriwates |
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| Publication Number | Publication Date |
|---|---|
| RO105079B1 true RO105079B1 (en) | 1995-01-27 |
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| Application Number | Title | Priority Date | Filing Date |
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| RO14312189A RO105079B1 (en) | 1989-12-11 | 1989-12-11 | Salicilhydrazidone new deriwates |
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| RO (1) | RO105079B1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002070464A3 (en) * | 2001-01-22 | 2004-01-22 | Arpida Ag | Hydrazones and their therapeutic use |
| WO2010083316A3 (en) * | 2009-01-14 | 2010-11-18 | Dow Agrosciences Llc | Fungicidal compositions including hydrazone derivatives and copper |
-
1989
- 1989-12-11 RO RO14312189A patent/RO105079B1/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002070464A3 (en) * | 2001-01-22 | 2004-01-22 | Arpida Ag | Hydrazones and their therapeutic use |
| WO2010083316A3 (en) * | 2009-01-14 | 2010-11-18 | Dow Agrosciences Llc | Fungicidal compositions including hydrazone derivatives and copper |
| US8455394B2 (en) | 2009-01-14 | 2013-06-04 | Dow Agrosciences, Llc | Fungicidal compositions including hydrazone derivatives and copper |
| US8461078B2 (en) | 2009-01-14 | 2013-06-11 | Dow Agrosciences Llc | Fungicidal compositions including hydrazone derivatives and copper |
| US8476194B2 (en) | 2009-01-14 | 2013-07-02 | Dow Agrosciences, Llc | Fungicidal compositions including hydrazone derivatives and copper |
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