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\def\RunningAuthor{Khudheyer Jawad Kadem}
\firstPage{3143}
\articleType{Original Article}
\receivedDate{03 May 2020}
\acceptedDate{08 jun 2020}
\revisedDate{01 jun 2020}
\journalVolume{2020, 11}
\journalIssue{3}
\journalDoi{ijrps.v11i3.2427}
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\title{\textbf{Synthesis and Characterization of New Heterocyclic Compounds}\textbf{\space }\textbf{from Calix [4] arene Derivative} \textbf{\space }}
\author{Khudheyer~Jawad~Kadem\textsuperscript{*}~\\[5pt]{Department of Chemistry, College of Science, University of Babylon, Hilla, Iraq }}

\begin{abstract}
In this work, a new heterocyclic compounds derived from Calix[4]arene Derivative had been synthesized. The characterization of the produced compounds was performed using melting point, FT-IR spectroscopy and some of them with \ensuremath{^{1}}H-NMR spectroscopy. The spectral data confirm the formation of these compounds. This research includes the following two parts:- Part 1\textbf{: } Synthesis of Calix[4]arane Derivative from reaction Calix[4]arane with 4-Aminobutyric acid to produce ester compound this part4-Aminobutyric acid reaction with freshly distilled thinly chloride , the produce final was purified via distillation below pressure reduced. The product was purified by repeated recrystallization. In this step Converted the substituted carboxylic acid to substituted acid chloride included to obtained good leaving group the compound product containing primary amine and the reaction of Calix[4]arane Derivative with compounds containing carbonyl group(aldehyde or ketone) the carbonyl group of aldehyde or ketone react with primary amine to produce imine compounds (Schiff bases. Part 2: Reaction of produced Schiff base compounds with mercaptoacetic acid (thioglycolic acid) or maleic anhydride to synthesized new heterocyclic compounds with heterogeneous ring are characterized by having many biological activities Which attracts the attention of researchers, and accordingly various derivatives containing sulfur or oxygen were prepared for heterocyclic compounds, these prepared compounds can have inhibitory activity for some bacteria, fungi, and viruses. 
\end{abstract}\def\keywordstitle{Keywords}

\begin{keywords}Calix[4]arane Derivative,\newline mercaptoacetic acid,\newline maleic anhydride
\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}
Calix [n] arans are a result of the condensation of p-alkyl-substituted formaldehyde and phenols in the existence of alkali. 

The cavity size cavity of calix[n]aranes container various (e.g., n = 4-8), they have many characterestics analogous to those of cyclodextrins and crown ethers. 

Studies current on the synthesis of calixarene derivatives had promised the expansion of spectrofluorometricion, sensors optical and electrodes selective \unskip~\citep{800319:19099463,800319:19099474}. 


\begin{table*}[!htbp]
\caption{\boldmath {Possessions the physical compounds Schiff's bases} }
\label{tw-1e2fcdcbcc2f}
\def\arraystretch{1.1}
\ignorespaces 
\centering 
\begin{tabulary}{\linewidth}{p{\dimexpr.2605\linewidth-2\tabcolsep}p{\dimexpr.2022\linewidth-2\tabcolsep}p{\dimexpr.26240000000000002\linewidth-2\tabcolsep}p{\dimexpr.27490000000000002\linewidth-2\tabcolsep}}
\tbltoprule \rowcolor{kwdboxcolor}Compound symbol  & Color & Melting points/\ensuremath{^{o}}C & Yield \%\\
\tblmidrule 
A1 &
  Gray  &
  118-119 &
  75\\
A2 &
  Gray  &
  119-121  &
  73\\
A3 &
  Grey &
  122-123  &
  83\\
A4 &
  Gray &
  133-132 &
  78\\
\tblbottomrule 
\end{tabulary}\par 
\end{table*}
Calixarenes possess widely utilizer as receptors and ionophores. Their derivatives, inclusive substituted benzene-like molecules and benzene like calixpyridines, need extensively travelled for intriguing self-assembly of nanooptical materials nanoelectronic, and several, structures crystal exhibiting exceptional architecture have reported \unskip~\citep{800319:19099464,800319:19099468}. 

Calixarenes are cyclic oligomers of the base condensation catalyzed reaction between ormaldehyde and p-substituted phenols. 

The caability of calixarenes to interact with cations was established via coworkers and Izatt in 1985 who appear that carrying of cations metal alkali from a basic phase aqueous source to an aqueous phase receiving can be accompleshed during an membrane chloroform organic in which calixarenes was dissolved \unskip~\citep{800319:19099477,800319:19099471}. 

The study and synthesis of calix(4)aranes with chains side attach to lesser rim include donor atoms soft is too an area of interest current with the object of resulting receptors selactive of cations metal soft \unskip~\citep{800319:19099466,800319:19099476}. Representative like the reported via \unskip~\citep{800319:19099465,800319:19099475}. 

Study the Organic films thin widly as sensitive chemical interfaces for acoustic wave based sensors chemical,10-12 and many like materials have demonstreted to have high selectivities to special chemical classes of analytes of vapor-phase. More molecules recently receptor able of take part in host-guest interactions for VOCs, like calixarenes and cyclodextrins19 \unskip~\citep{800319:19099478,800319:19099472}. 

Many infectious diseases are occasion via pathogenic bacteria contain tuberculosis, anthrax, dysentery, plague, etc. 

Furthermore, histoplasmosis, candidiasis, ringworm, or diseases are attributed to fungi. Kingston defined antime crobial agent as an agent that kills microorganesms or decrease the growth \unskip~\citep{800319:19099473,800319:19099467}.

\textbf{Synthesis to converted carboxylic acid to acyl substituted chloride }

In a two-nick round bottom flask equipped with a thermostat, distillation funnel and a stirrer magnetic, 4-Aminobutyric acid (0.48 mol) was placed in an ice bath for 10 min, then 350ml of thionyl chloride was added gradually, stirring for half an hour with continuous stirring for two hour until the color changes. 

Increase of thionyl chloride is distilled under breached pressure. The acid chloride is used directly in the reaction.

\textbf{Synthesis of Schiff's bases from amino group of calix derivative}

To a 250 ml round bottom flask containing 0.01 mol of amino compound dissolved in 25 ml absolute ethanol a 0.04 mol of (benzaldehyde or 4-hydroxy benzldehyde or vinilline or acetophenone) dissolved in 50 ml absolute ethanol (hot) was added. 

A few glacial acetic acid drops used as a catalyst and the mixture was refluxed at 75 \ensuremath{^{o}}C with stirring for 3-6 hour \unskip~\citep{800319:19099470}. 

After cooling at room temperature precipitate was formed, filtered off, washed with ethanol and diethyl ether, air dried and recrystallized from THF. 

\textbf{Synthesis of heterocyclic compounds} \textbf{\space }

A series of heterocyclic compounds have been synthesized through reaction of Schiff bases with mercaptoacetic acid or maleic anhydride.

\textbf{Synthesis heterocyclic compound contains of 1,3-Oxazepine derivatives }

Schiff's base mixture, (0.1 mole) and (0.4 mole) amount of were reacted maleic anhydride in 20 ml DMF, (little drops of glacial A.A) at 70 \ensuremath{^{o}}C heated (8-10 h) \unskip~\citep{800319:19099469,800319:19099479} the solution was reduced by the rotary evaporator and allowable to cool at room temperature. 

The product was obtained by decantation, washed three times with small portions of DMF and diethyl ether, air dried and was recrystallized from a suitable solvent.


\begin{table*}[!htbp]
\caption{\boldmath {Possessions of the physical compounds heterocyclic.} }
\label{tw-0cc9883fceac}
\def\arraystretch{1.1}
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\centering 
\begin{tabulary}{\linewidth}{p{\dimexpr.2967\linewidth-2\tabcolsep}p{\dimexpr.2656\linewidth-2\tabcolsep}p{\dimexpr.2223\linewidth-2\tabcolsep}p{\dimexpr.2154\linewidth-2\tabcolsep}}
\tbltoprule \rowcolor{kwdboxcolor}Compound symbol  & Color & Melting points/oC & Yield \%\\
\tblmidrule 
A5  &
  Dark black  &
  110-112 &
  76\\
A6 \mbox{}\protect\newline  &
  Dark black &
  116-118 &
  65\\
A7 \mbox{}\protect\newline  &
  Grey &
  108-110 &
  68\\
A8 \mbox{}\protect\newline  &
  Dark gray &
  123-124 &
  77\\
A9 \mbox{}\protect\newline  &
  Dark black &
  126-127 &
  73\\
A10 \mbox{}\protect\newline  &
  Dark black &
  126-1-27 &
  62\\
A11 \mbox{}\protect\newline  &
  Dark black &
  118-120 &
  66\\
A12 \mbox{}\protect\newline  &
  Dark black &
  133-134 &
  61\\
\tblbottomrule 
\end{tabulary}\par 
\end{table*}

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\caption{\boldmath {Show converted the substituted carboxylicacid to acid chloride.}}
\label{f-9816b0bab89d}
\end{figure*}
\egroup

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\caption{\boldmath {Reaction of theacid chloride with hydroxyl group toproduct ester group.}}
\label{f-866f494ce822}
\end{figure*}
\egroup

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\centering \makeatletter\IfFileExists{images/1710486f-b2b0-4ab6-9905-83584a0faf6e-upicture3.png}{\includegraphics{images/1710486f-b2b0-4ab6-9905-83584a0faf6e-upicture3.png}}{}
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\caption{\boldmath {The obtained product from Figure 2 was reactedwith a aldehyde or ketone to obtain different Schiff bases.}}
\label{f-73ecbbb050fc}
\end{figure*}
\egroup

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\caption{\boldmath {Structures of Schiff's bases.}}
\label{f-8353440c3c42}
\end{figure*}
\egroup

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\caption{\boldmath {The Schiff bases resulted from different aldehyde were reacted withmercaptoacetic acid (thioglycolic acid) or maleic anhydride to obtainheterogeneous cyclic compounds}}
\label{f-b7dc88b7f373}
\end{figure*}
\egroup

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\caption{\boldmath {The Schiff basesresulted from the acetophenone were interacted with the maleic anhydride ormercaptoacetic acid to obtain heterogeneous cyclic compounds.}}
\label{f-8a65be759ebb}
\end{figure*}
\egroup

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\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/08f89e94-6233-4132-95b1-ab79444f4a76-upicture7.png}{\includegraphics{images/08f89e94-6233-4132-95b1-ab79444f4a76-upicture7.png}}{}
\makeatother 
\caption{\boldmath {Heterocyclic compound structures.}}
\label{f-4eb4b03f7891}
\end{figure*}
\egroup

    
\section{Results and Discussion}
4-Aminobutyric acid (0.48 mol), 350 ml of freshly distilled thinly chloride and dioxane of a drop was refluxed in a boiling water-bath for 2 hours. The produce final was purified via distillation below pressure reduced. The product was purified by repeated recrystallization. Its chemical structure and purity were confirmed by IR, The absence of the absorption beam in the 2400-3500 cm\ensuremath{^{-1}} region indicates the broad beam of the hydroxyl group and melting-point that changed from 195 \ensuremath{^{0}}C to 183 \ensuremath{^{0}}C measurement. Figure~\ref{f-9816b0bab89d} shows Converted the substituted carboxylic acid to acid chloride.

(4 mmole) of amino acyl chloride is added to 1 mmole Calix[4]arene, then the mixture is heated at a temperature not exceeding (70 \ensuremath{^\circ} C) for a period of (6 hour). 

The excess of the solvent is separated using a rotary evaporator. The reaction is shown in Figure~\ref{f-866f494ce822} represent reaction the acid chloride with hydroxyl group to product ester group.

The disappearance of the absorption band in the region indicates the 3250-3500 cm\ensuremath{^{-1}} broad band belonging to the phenolic hydroxyl group.

Also disapparance of the band absorption at 3300-3500 cm\ensuremath{^{-1}} for amine group and the emergence of a new package for the ester group at 1745 cm\ensuremath{^{-1}} for the carbonyl group of ester.

After obtaining the result in Figure~\ref{f-866f494ce822}, the product was reacted with a aldehyde or ketone to obtain different Schiff bases, and it can be represented in equation in Figure~\ref{f-73ecbbb050fc} and the resulting compounds are diagnosed by the melting point, color, infrared spectrum, and NMR spectrum.

The compounds in the above were diagnosed by infrared, where the sad group of the trustee disappeared in 3300-3500 cm\ensuremath{^{-1}} and the disappearance of a group of carbonyl for aldehyde or ketone was between 1710-1725 and the emergence of a new package for all the compounds in 1690 {\textendash} 1640 cm\ensuremath{^{-1}} the imine groups return (schiff bases). 

Also, it was diagnosed by NMR, and the beam belonging to the amine group was disappeared in (3- 5)ppm, and this confirms that the resulting right-hand group (scheff bases) is obtained. Structures and properties of the physical of schiffs bases compounds are itemized in Figure~\ref{f-8353440c3c42} and Table~\ref{tw-1e2fcdcbcc2f}.

After obtaining different Schiff bases from different aldehyde, the resulting compounds were reacted mercaptoacetic acid (thioglycolic acid) or maleic anhydride as well as the compound to obtain heterogeneous cyclic compounds as shown in Figure~\ref{f-b7dc88b7f373} and the resulting compounds were diagnosed by melting point, color, infrared spectrum and NMR spectrum.

Likewise, after obtaining the Schiff bases resulting from the acetophenone, it was interacted with the maleic anhydride or mercaptoacetic acid as well as the compound to obtain heterogeneous cyclic compounds as shown in the Figure~\ref{f-8a65be759ebb} and the resulting compounds were diagnosed by the melting point, color, infrared spectrum and H-NMR spectrum.

Structures and possessions physical of heterocyclic compounds are itemized in Figure~\ref{f-4eb4b03f7891} and Table~\ref{tw-0cc9883fceac}.

The heterocyclic compounds in the above were diagnosed by infrared, where the disappeared in 2550 cm\ensuremath{^{-1}} return to mercaptans S-Hand the disappearance of a group of1690 {\textendash} 1640 cm\ensuremath{^{-1}} the imine groups return (schiff bases). 

And appeared of a new package for all the compounds in Also, it was diagnosed by HNMR, was contaminated by disappearing the signal that attributed for azomethine proton at 8-9 ppm and appearing signal at (7-8) attributed for (O-CH-N) also appearing signals attributed for protons of Oxazepine cycle in the range of (6-7) ppm, this is consider a good evidence for the preparation of 1,3-oxazepine 

Compounds with heterogeneous ring are characterized by having many biological activities Which attracts the attention of researchers, and accordingly various derivatives containing sulfur or oxygen were prepared for heterocyclic compounds, these prepared compounds can have inhibitory activity for some bacteria, fungi, and viruses.
    
\section{Conclusions}
Synthesis of Calix[4]arane Derivative from Calix[4]arane reaction with 4-Aminobutyric acid to produce ester compound and group (aldehyde or ketone) to produce imine compounds (Schiff bases). Reaction of produced Schiff base compounds with mercaptoacetic acid (thioglycolic acid) or maleic anhydride to synthesized new heterocyclic compounds. 
\section*{Acknowledgement}Author deeply thanks for the University of Babylon/ College of science to support us in facilities and another requirements.

\textbf{Conflict of interest}

None

\textbf{Funding support}

None
    

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