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\def\RunningAuthor{Khudheyer Jawad Kadem}
\firstPage{1006}
\articleType{Original Article}
\receivedDate{02 Jun 2020}
\acceptedDate{11 Aug 2020}
\revisedDate{01 Jul 2020}
\journalVolume{2020, 11 (SPL4)}
\journalDoi{ijrps.v11iSPL4.4236}
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\title{\textbf{Synthesis of Heterocyclic Compounds Containing Sulphur From }\textbf{Ethylene Diamine Tetra Acetic acid} \textbf{ Derivatives}}
\author{Khudheyer~Jawad~~Kadem\textsuperscript{*}~\\[5pt]{Department of Chemistry, College of Science, University of Babylon, Iraq}}

\begin{abstract}
In this work, three novel Schiff's bases subsidiaries were set up from Ethylene Diamine Tetra Acetic corrosive Derivatives(K1, K2 and K3); (K1) which was blend from response of EDTA with 4-hydroxybenzaldehyde and 2,4-dintrophenyl hydrazine. (K2) which was union from response of EDTA with vinilline and 2,4-dintrophenyl hydrazine. (K3) which was amalgamation from response of EDTA with 4-aminoacetophenone and 2,4-dintrophenyl hydrazine after that combination three novel hetrocyclic compound Containing Sulfur molecule; Derivative with compounds containing carbonyl group (aldehyde or ketone) the carbonyl group of aldehyde or ketone react with primary amine to produce mine compounds (Schiff bases), Reaction of produced Schiff base compounds with mercaptoacetic acid (thioglycolic acid) to synthesized new heterocyclic compounds Compounds with heterogeneous ring are characterized by having many biological activities Which attracts the attention of researchers, and accordingly various derivatives containing sulfur were prepared for heterocyclic compounds, these prepared compounds can have inhibitory activity for some bacteria, fungi, and viruses. (M1, M2 and M3) which were union from response of (K1, K2 and K3) individually with marcaptoacetic acid. All of the Schiff's bases derivatives and hetrocyclic compound\textbf{\space }Containing Sulphur atom were characterized and identified by spectroscopic methods (FT-IR and \ensuremath{^{1}}H-NMR) spectroscopies. 
\end{abstract}\def\keywordstitle{Keywords}

\begin{keywords}EDTA derivative,\newline cycloaddition,\newline Schiff's bases
\end{keywords}
\twocolumn[ \maketitle {\printKwdAbsBox}]
\makeatletter{\raggedright\textsuperscript{*}Corresponding Author\par Name:\ Khudheyer~Jawad~~Kadem~\\ Phone:\ ~\\  Email:\ khudheyerbabel@yahoo.com
        \par}\vspace*{-11pt}\hrulefill\par{\fontsize{12}{14}\selectfont ISSN: 0975-7538}\par% 
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\section{Introduction}
In view of its phenomenal chelating capacity, ethylenediaminetetraacetic acid (EDTA) has been utilized as an adsorbent of substantial metal particles produced from the mechanical procedures \unskip~\citep{848908:19974568,848908:19974572}, and in natural contaminations that cause acid downpour and exhaust cloud \unskip~\citep{848908:19974574,848908:19974573}

Moreover, EDTA has been utilized for flushing radioactive isotopes in atomic office cleaning \unskip~\citep{848908:19974564}. The vast majority of the radioactive fluid wastes (RLWs), that are produced during the activity and from the decommissioning of atomic power plants, ordinarily contain a high EDTA fixation, with different sorts of surfactants \unskip~\citep{848908:19974570,848908:19974565}. 

The EDTA contained in the RLWs exists as a complex with radioactive isotopes, which makes EDTA hard to evacuate by traditional water treatment strategies, for example, substance precipitation and filtration. Specifically, it has been accounted for that more than 10 ppm EDTA couldn't be isolated by the customary concoction process \unskip~\citep{848908:19974566}.


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\caption{\boldmath {The reaction of tetracarboxylic acids group and thionyl chloride}}
\label{f-cc854ab184f7}
\end{figure*}
\egroup

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\makeatother 
\caption{\boldmath {The structure of K1 and K2}}
\label{f-2141a5315682}
\end{figure*}
\egroup
Schiff bases are mixes of containing C=N gathering. They are regularly incorporated from amine and aldehyde or ketone. Schiff bases have picked up significance because of their application in numerous pharmacological exercises like antibacterial \unskip~\citep{848908:19974568,848908:19974572}, antifungal \unskip~\citep{848908:19974562}, hostile \unskip~\citep{848908:19974569}, to proliferative. Antitumor \unskip~\citep{848908:19974570}, and antipyretic properties. Schiff bases with aryl substituents are increasingly steady and promptly orchestrated. Though those containing alkyl substituent is generally unsteady. Schiff bases of aliphatic aldehydes are shaky and promptly polymerizable while those with fragrant aldehydes having powerful conjugation are increasingly steady \unskip~\citep{848908:19974566} Schiff bases are buildup results of essential amines with carbonyl mixes and they were first announced by Schiff \unskip~\citep{848908:19974568}, in 1864. The normal auxiliary component of these mixes is the azomethine bunch with a general equation RHC=N-R1, where R and R1 are alkyl, aryl, cyclo alkyl or heterocyclic gatherings which might be differently subbed. These mixes are likewise knows as anils, imines or azomethines. A few investigations \unskip~\citep{848908:19974572}, indicated that the nearness of a solitary pair of electrons in a sp2 hybridized orbital of nitrogen molecule of the azomethine bunch is of impressive compound and organic significance. Due to the overall effortlessness of readiness, manufactured adaptability, and the unique property of C=N gathering, Schiff bases are commonly great chelating agents, \unskip~\citep{848908:19974565} particularly when an utilitarian gathering like {\textendash}OH or {\textendash}SH is available near the azomethine gathering in order to frame a five or six membered ring with the metal particle \unskip~\citep{848908:19974563}. Adaptability of Schiff base ligands and organic, explanatory and mechanical utilizations of their edifices make further examinations here profoundly alluring. 


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\caption{\boldmath {The structure of K3}}
\label{f-af0550333dd7}
\end{figure*}
\egroup

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\caption{\boldmath {The structure of M1, M2 and M3}}
\label{f-dd142341977e}
\end{figure*}
\egroup
The attention of the organic chemists has been directed towards the field of heterocyclic chemistry, because their valuable utilities in the synthesis of variety of biologically active derivatives. Heterocyclic compounds occur very widely in nature and are essential to life. Nitrogen-containing heterocyclic entities exist in many natural products and chemotherapeutic agents. Their attachment to sugar molecules either as thioglycoside or nucleoside analogues, plays an important role in vitalbiological processes as well as in the synthetic organic chemistry \unskip~\citep{848908:19974571}.

\textbf{Synthesis of Acid chlorides}

To a dry powder of ethylenediaminetetraacetic acid (EDTA)  (0.022 mole) in claisen Flask was added excess redistilled thionyl chloride and the mixture was refluxed for two hour or until the evolution of hydrogen chloride ceases. The reaction mixture was left to cool, then condenser was removed and the flask was heated at 60 c\ensuremath{^{o}} for five minutes with occasional shaking to give a yellow product of EDTA acylchloride \unskip~\citep{848908:19974567}. 

\textbf{Synthesis of ethylene diamine tetra acetic acid derivatives}

\textbf{Part one}

Response carboxylic acid gathering of EDTAcylchloride with hydroxyl bunch compound to arrangement ester group(F1,F2).To a 250 ml round base cup containing (0.024 mole of EDTA,7.17gm), (0.088molof 4-hydroxy Benzaldehyde, or vinilline) broke up in 50ml DMF, and (0.032mole, of EDTA acylchloride), (0.032mol of vanillin, 20gm) in 50ml DMF were included and the response blend was warmed at 90-100 \ensuremath{^{o}}C with nonstop mixing for10-24hr,The item was gathered by vacuum filtration and was dried under high vacuum.Yield 78-79\%. The response was trailed by (TLC) procedure. The precious stones shaped were then isolated. The other unrefined got was purged by extraction with CCl4/Dioxan (1:2). 

\textbf{Part two}

Response of EDTAcylchloride with amino gathering to development in the midst of compound (F3). To a 250ml round base carafe containing EDTAcylchloride (0.022mole, 6.486gm.) disintegrated in 50 ml N, Ndimethyl formamide (DMF) a blend of (0.088mol, 3.00gm4-aminoacetophenone) broke up in50ml DMF and a few drops of pyridine, there activity blend was warmed at90-100\ensuremath{^{o}}C with nonstop mixing for3-4hr(1), The item was gathered by vacuum filtration and was dried under high vacuum. Yield 80\%. The gems framed were then isolated. The other rough acquired was decontaminated by extraction with CCl4/Dioxan (1:2).

\textbf{Synthesis of Schiff's bases(K1) from ethylene diamine tetra acetic acid derivatives (F1)} \textbf{\space }

To a 250ml round base flagon containing 0.002mol (2.23gm) of F1 broke up in 25 ml total liquor a 0.01mol of (2,4-dintrophenyl hydrazine) disintegrated in 50 ml total liquor was included 1-3 drops of icy acidic corrosive was utilized as impetus and the response blend was refluxed at 75-100\ensuremath{^{o}}C with mixing for 10-24h. In the wake of cooling at room temperature hasten was shaped, the hued arrangement was vanished by rotating evaporator at 50\ensuremath{^{o}}C; the item was washed with diethyl ether and recrystallized with chloroform. TLC (Dichloromethane: petroleum ether).\textbf{\space }

\textbf{Synthesis of Schiff's bases (K2) from ethylene diamine tetra acetic acid derivatives (F2)} \textbf{\space }

To a 250 ml round base carafe containing 0.002 mole (2.00gm) of F2 broke down in 25 ml outright ethanol a 0.01mol of (2,4-dintrophenyl hydrazine) disintegrated in50ml total liquor was included 1-3 drops of frigid acidic corrosive was utilized as impetuses and the response blend was refluxed at 75-100\ensuremath{^{0}}C with mixing for10-24 h. Subsequent to cooling at room temperature accelerate was shaped, the item was washed with diethyl ether and recrystallized with chloroform. TLC (dichloromethane: petroleum ether\textbf{).}

\textbf{Synthesis of Schiff's bases (K3) from ethylene diamine tetra acetic acid derivatives (F3)} \textbf{\space }

To a 250 ml round base flagon containing 0.002 mole (2.12gm) of F2 broke down in 25 ml total ethanol a 0.01mol of (2,4-dintrophenyl hydrazine) disintegrated in50ml supreme liquor was included 1-3 drops of icy acidic corrosive was utilized as impetuses and the response blend was refluxed at 75-100 oC with mixing for10-24 h. Subsequent to cooling at room temperature accelerate was framed, the item was washed with diethyl ether and recrystallized with chloroform. TLC (dichloromethane: petroleum ether).\textbf{\space }

\textbf{Synthesis of heterocyclic compounds }\textbf{(}\textbf{M1-M2} \textbf{) Derived from Schiff Bases (K1-K2)}

The blend of (M1-M2) is displayed in Path 8and 9. The dioxane arrangement of (25ml) Schiff base (K1-K2) (1.0 mole) is blended in with dioxane arrangement of (25ml) mercaptoacetic corrosive (4 Mole) and includes 3-4 drops of acidic corrosive with utilized (15 mg) ZnCl2 reactant. At that point the blend is mixed for 8-24hours by utilizing attractive stirrer at 60-95\ensuremath{^\circ}C. He em power procured were filtered washed with ethanol likewise, dried and were re-set from ethanol.

\textbf{Synthesis and Characterization of Some Heterocyclic Compounds (}\textbf{M3} \textbf{) derived from Schiff bases (K3)}

The combination of (M3) is introduced in Path 12and 13. The dioxane arrangement of (25ml) Schiff base (K3) (1.0 mole) is blended in with dioxane arrangement of (25ml) mercaptoacetic corrosive (4 Mole) and includes 3-4 drops of acidic corrosive with utilized (15 mg) ZnCl\ensuremath{_{2}} reactant. At that point the blend is mixed for 8-24hours by utilizing attractive stirrer at 60-95\ensuremath{^\circ}C. he support obtained were filtered washed with methanol likewise, dried and were re-set from.
    
\section{Results and Discussion}
The production of Tetra chloride\textbf{\space }was supported out by the reaction of tetra carboxylic acids group and thionyl chloride (see Figure~\ref{f-cc854ab184f7}); it is well recognized.

One preferred position of utilizing thionyl chloride for the planning of alkyl chlorides is that the side-effects of the response are gases. The response happens by anucleophilic acyl substitution pathway in which the carboxylic corrosive is first changed over into a chlorosulfite transitional, in this way supplanting - OH of the corrosive with much better leaving gathering. FTIR spectrum (cm\ensuremath{^{-1}}) for [EDTA tetra acyl chloride] showed stretching bands at 1785-1805, for (carbonyl group) carboxylic acid chlorides.

The esterification of ethylene diamine tetra acetic corrosive acylchloride in a hot acidic medium offers ascend to unclean items. In every one of esterification response, p-hydroxyl Benz aldehyde or vinilline were utilized as a vehicle of response, though pyridine as accepter to hydrogen chloride to shape pyridinum chloride which expelled from response blend by extraction with refined water these item spoke to in structure K1 and K2 (Figure~\ref{f-2141a5315682}).

The amide formation when the reaction of ethylenediamine tetra acetic acid acylchloride with 4-aminoacetophenone. These product represented in structure K3 (Figure~\ref{f-af0550333dd7}).

\textit{\textbf{FT-IR Spectra}}

The FT-IR spectra of the prepared compounds (K1,K2 and K3) were not showed the band attributed to the \ensuremath{\upsilon } (bonding O-H) of vanillin, 4-hydroxybenzaldehyde and 4-aminoacetophenone at (3360-3580) cm\ensuremath{^{-1}} while a strong band attributed to \ensuremath{\upsilon } (C=0) at (1732-1550 cm\ensuremath{^{-1}}) was appeared which conform the formation of ester compound(K1,K2), and band of carbonyl group of amid formation group of k3 compound at \ensuremath{\upsilon } (C=O) was appeared at (1628- 1558 cm\ensuremath{^{-1}}).

\ensuremath{^{\textit{\textbf{1}}}} \textit{\textbf{H-NMR Spectra }}

The\ensuremath{^{ 1}}H-NMR spectra were recorded for the novel Schiff's bases derivatives (K1,K2 and K3); The \ensuremath{^{1}}H-NMR spectrum for compound K1 was appeared the following characteristic signals (ppm). (7.3-8.8, aromaticprotons), (3.5,N-CH2-CH2-N), ( 4.0,N-NH-), ( 3.2,1H,-NCH-CO). The 1H-NMR spectrum for compound K2 was appeared the following characteristic signals (ppm). (7.3-8.9, aromaticprotons), ( 3.9,O-CH3), (4.1,N-NH- CO), (3.4,-NCH- CO), (2.3,N-CH2CH2-N). The 1H-NMR spectrum for compound K3 was appeared the following characteristic signals (ppm). (7.2-8.8, aromaticprotons), (3.1,-CH3),(7.1 ,-NH-),(2.5,-NCH2CH2N-), (3.5,-N-CH2-CO). The\ensuremath{^{ 1}}HNMR spectra were recorded for the three novel hetrocyclic compound\textbf{\space }Containing Sulphur atom ; (M1,M2 and M3) (see Figure~\ref{f-dd142341977e}). The 1H-NMR spectrum for compound M1 was appeared the following characteristic signals (ppm). (7.0-9.0, aromaticprotons), (6.0,- N- CH-S-), (3.5, -N-CH2-CO), (4.0, -NH-) (2.4,-N-CH2-CH2-N-). The 1H-NMR spectrum for compound M2 was appeared the following characteristic signals (ppm). (7.2-9.1, aromaticprotons), (6.2,- N-CH-S-), (3.3, -N-CH2-CO), (4.0, -OCH3) (2.5,-N-CH2-CH2-N-). The 1H-NMR spectrum for compound M3 was appeared the following characteristic signals (ppm). (7.3-9.2, aromaticprotons), (6.2,- N-CH-S-), (3.3,-N-CH\ensuremath{_{2}}-CO), (7.3, -NH-)(2.5,-N-CH\ensuremath{_{2}}-CH\ensuremath{_{2}}-N-).
    
\section{Conclusions\textbf{\space }}
This made Schiff's bases, used as starting materials for the creation of some heterocyclic composite containing sulphur atom through the cycloaddition reaction using acid as a reagent, a series of some new and novel heterocyclic have been synthesized using acid catalysis the results have shown an excellent anti-bacterial activity.

\textbf{Conflict of Interest}

The authors declare that they have no conflict of interest for this study.

\textbf{Funding Support}

The authors declare that they have no funding support for this study. 
    

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