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\begin{document}


\def\RunningAuthor{Sarah Mohammed Abed and Hasan Thamer Ghanem}
\firstPage{3186}
\articleType{Original Article}
\receivedDate{21.05.2019}
\acceptedDate{23.09.2019}
\revisedDate{18.09.2019}
\journalVolume{10}
\journalIssue{4}
\journalDoi{ijrps.v10i4.1621}
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\title{Synthesis and characterization Some of heterocyclic compounds from Nitrogen derivative}
\author{Sarah~Mohammed~Abed\textsuperscript{*}, 
            Hasan~Thamer~Ghanem~\\[5pt]{Faculty of Education for Girls\unskip, University of Kufa, Iraq}}

\begin{abstract}
This paper involves the synthesis of new oxazepine derivatives by multi-reaction steps. The first step synthesis azo derivative from 2-naphthol with 3-aminoacetophenone. The second step was the condensation reaction between ketone group of the azo compound and different primary aromatic amines (4-amino phenol, 3-nitro aniline and 4-methyl aniline) to yiled new azo Schiff base compounds (S1-S3) respectively. In the final step, Oxazepine compounds (L1-L3)and (L4-L6)were prepared from reaction imine compounds (S1-S3) with maleic and phthalic anhydride in toluene as solvent. All these derivatives were characterized by melting point, FTIR, HNMR and 13CNMR. 
\end{abstract}\def\keywordstitle{Keywords}

\begin{keywords}Azo compounds,\newline multi-reaction steps,\newline Schiff bases,\newline Oxazepine
\end{keywords}
\twocolumn[ \maketitle {\printKwdAbsBox}]
\makeatletter{\raggedright\textsuperscript{*}Corresponding Author\par Name:\ Sarah~Mohammed~Abed~\\ Phone:\ ~\\  Email:\ Sarah.albrahimi54@gmail.com
        \par}\vspace*{-11pt}\hrulefill\par{\fontsize{12}{14}\selectfont ISSN: 0975-7538}\par% 
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\section{Introduction}
The chemistry of heterocyclic compounds has been an interesting field of study \unskip~\citep{590513:13708031} for a long time due its more application in several fields such as medicinal, pharmaceutical and selective drugs \unskip~\citep{590513:13708032} Oxazepine stands for unsaturated non-homologous seven associated heterocycle having Oxygen in position 1 and nitrogen in position 3 along with five carbon atoms \unskip~\citep{590513:13708033}. Oxazepine has three isomers bases on the location of oxygen and nitrogen atoms in the seventh ring \unskip~\citep{590513:13708034}. 


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\caption{\boldmath {Oxazepine with three isomers bases}}
\label{f-0a9c6bd7c8e5}
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\egroup
 It is organized through the Pericycliccyclo addition of Schiff bases with maleic and phthalic anhydrides \unskip~\citep{590513:13708035}. Oxazepine derivatives have a huge diversity of biological activities like antifungal \unskip~\citep{590513:13708036}, hypotic muscle relaxant \unskip~\citep{590513:13708037}, antibacterial \unskip~\citep{590513:13708038} telomerase inhibitors \unskip~\citep{590513:13708039}, anti-inflammatory \unskip~\citep{590513:13708040} and antiepileptic \unskip~\citep{590513:13708041} (1,4)Oxazepine was taken up to designing potent progesterone receptor antagonists \unskip~\citep{590513:13708042}. (1,4) Oxazepine is found to be a dynamic moiety in numerous psychoactive pharmaceuticals \unskip~\citep{590513:13708043}. 
    
\section{\textbf{Preparation Methods}}
The methods of chemical preparations are as below in details. Table~\ref{tw-f6263fbe99db} shows the physical features of organized compounds. 

\textbf{(1) Synthesis1-(3-((2-hydroxy naphthalene-1-yl)diazenyl)acetophenone }

 3-aminoacetophenone (0.03 mol, 4.05 gm) was dissolved in (3ml)of concentrated hydrochloric acid and (20 ml) of distilled water. The solution was cold at (0 c\ensuremath{^{o}}) in an ice-water bath. The sodium nitrite (0.03 mol, 2.07 gm)was dissolved in (10 ml) of distilled water and added dropwise to the solution with stirring .2- naphthol (0.03 mol, 4.32 gm) was dissolved in (20 ml) of ethanol and (10 ml) of sodium hydroxide 10\% and cooled to (0C\ensuremath{^{o}}), added to the diazonium solution is dropwise and stirring at (0C\ensuremath{^{o}})for (2h) for obtaining the coupling agent. The result of the orang gold compound was precipitated, filtered and washed with water\textbf{. }

\textbf{(2)Synthesis of azo Schiff bases derivatives (S\ensuremath{_{1-}}S\ensuremath{_{3}})}

Ethanolic mixture (30 ml) containing 1 drop of concentrated hydrochloric acid to azo acetophenone derivative (A) of (0.003 mol, 1.0 gm)then adding (0.37gm, 0.47gm, 0.36 gm) of primary aromatic amines (4-amino phenol, 3-nitro aniline and 4- methyl aniline). The reaction mixture was refluxed with stirring for (10-35) hours at (78) C\ensuremath{^{o}}, the reaction was completed and examined by using TLC (Methanol: dry benzene 1:4)recrystallized from ethanol.\textit{\textbf{\space }}

\textbf{(3)Synthesis of (L\ensuremath{_{1}}-L\ensuremath{_{3}}) Oxazepine and (L\ensuremath{_{4}}-L\ensuremath{_{6}}) Oxazepine}

A mixture of azo-Schiff bases derivatives (S\ensuremath{_{1}}-S\ensuremath{_{3}}) (0.5gm, 0.3gm,0.3 gm) with (0.16 gm , 0.1 gm , 0.1gm) maleic anhydreid (0.25gm ,0.14gm ,0.11gm) phthalic anhydride respectively in (30 ml) of Tolouene , was refluxed for (19h, 6h ,33h) hours for compounds (L\ensuremath{_{1}}-L\ensuremath{_{3}}) and (19h,4h,32h) hours for compounds (L\ensuremath{_{4}}-L\ensuremath{_{6}}). 
\begin{table*}[!htbp]
\caption{\boldmath {Physical features of organized compounds} }
\label{tw-f6263fbe99db}
\def\arraystretch{1.1}
\ignorespaces 
\centering 
\begin{tabulary}{\linewidth}{p{\dimexpr.1254\linewidth-2\tabcolsep}p{\dimexpr.1565\linewidth-2\tabcolsep}p{\dimexpr.1981\linewidth-2\tabcolsep}p{\dimexpr.16\linewidth-2\tabcolsep}p{\dimexpr.16\linewidth-2\tabcolsep}p{\dimexpr.20\linewidth-2\tabcolsep}}
\tbltoprule \rowcolor{kwdboxcolor}Yiled \% & R.F & m.p \mbox{}\protect\newline co & M.wt  \mbox{}\protect\newline g{\tt\string\ \unskip}mol & m.f & Compound \mbox{}\protect\newline No.\\
\tblmidrule 
91 &
  --- &
  156-158 &
  290.32 &
  C\ensuremath{_{18}}H\ensuremath{_{14}}N\ensuremath{_{2}}O\ensuremath{_{2}} &
  A \\
87 &
  0.9 &
  162-164 &
  381.44 &
  C\ensuremath{_{24}}H\ensuremath{_{19}}N\ensuremath{_{3}}O\ensuremath{_{2}} &
  S1\\
81 &
  0.9 &
  160-162 &
  410.43 &
  C\ensuremath{_{24}}H\ensuremath{_{18}}N\ensuremath{_{4}}O\ensuremath{_{3}} &
  S2\\
87 &
  0.7 &
  174-176 &
  379.46 &
  C\ensuremath{_{25}}H\ensuremath{_{21}}N\ensuremath{_{3}}O\ensuremath{_{1}} &
  S3\\
70 &
  0.9 &
  108-110 &
  481.51 &
  C\ensuremath{_{28}}H\ensuremath{_{23}}N\ensuremath{_{3}}O\ensuremath{_{5}} &
  L1\\
93 &
  0.8 &
  136-138 &
  510.51 &
  C\ensuremath{_{28}}H\ensuremath{_{22}}N\ensuremath{_{4}}O\ensuremath{_{6}} &
  L2 \\
90 &
  0.9 &
  105-106 &
  479.54 &
  C\ensuremath{_{29}}H\ensuremath{_{25}}N\ensuremath{_{3}}O\ensuremath{_{4}} &
  L3\\
63 &
  0.9 &
  116-118 &
  529.55 &
  C\ensuremath{_{32}}H\ensuremath{_{23}}N\ensuremath{_{3}}O\ensuremath{_{5}} &
  L4\\
79 &
  0.8 &
  130-132 &
  558.55 &
  C\ensuremath{_{32}}H\ensuremath{_{22}}N\ensuremath{_{4}}O\ensuremath{_{6}} &
  L5\\
88 &
  0.9 &
  111-113 &
  527.58 &
  C\ensuremath{_{33}}H\ensuremath{_{25}}N\ensuremath{_{3}}O\ensuremath{_{4}} &
  L6\\
\tblbottomrule 
\end{tabulary}\par 
\end{table*}

    
\section{Results and Discussion}
The coupling reaction \unskip~\citep{590513:13708044} between diazonium salt with 2-naphthol to produce 1-(3((2-hydroxynaphthalen-1-yl)diazenyl) acetophenone. Azo-Schiff bases (S\ensuremath{_{1}}-S\ensuremath{_{3}}) were synthesized by condensation of the equimolar quantity of primary aromatic amines (4-amino phenol, 3-nitro aniline, 4-methal aniline) with azo acetophenone derivative (A). Apericyclic reaction \unskip~\citep{590513:13708045} is one that occurs by a concerted process through a cyclic transition state. The word concerted means that all bonding changes occure simultaneously; no intermediates are involved \unskip~\citep{590513:13708046}. Pericyclic reaction represents an imperative type of concerted (solitary step) processes including \ensuremath{\pi }-systems \unskip~\citep{590513:13708047} A concerted rearrangement of the electrons that causes \ensuremath{\delta } and \ensuremath{\pi }-bonds break and from to simultaneously \unskip~\citep{590513:13708036}. Apericyclic reaction between imine groups of azo-Schiff bases (S\ensuremath{_{1}}-S\ensuremath{_{3}}) as two membered compounds and cyclic acid oanhydride (maleic, phthalic anhydride)as five-membered compounds in Tluene were syntheized compounds (L\ensuremath{_{1}}-L\ensuremath{_{3}}) and (L\ensuremath{_{4}}-L\ensuremath{_{6}}) respectively \unskip~\citep{590513:13708038}. Scheme~\ref{f-42ef6f5a6cb4} depicts the mechanism of synthesis of 1,3-Oxazepine.


\bgroup
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\makeatother 
\caption{\boldmath {Mechanism of synthesis 1,3-Oxazepine}}
\label{f-42ef6f5a6cb4}
\end{scheme*}
\egroup
The structures of all synthesis compounds were depicted in Scheme~\ref{f-6cac09a0d123}. 


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\caption{\boldmath {Structures of each synthesized compounds}}
\label{f-6cac09a0d123}
\end{scheme*}
\egroup
\textbf{Spectral Characterization }

Our derivative identified with variety spectral methods like (FT.IR, H.NMR, C\ensuremath{^{13}}.NMR) spectra with microbial assay

\textbf{FT.IR Spectra of Derivatives}

The FT.IR Spectrums of derivatives are depicted in Figures~\ref{f-7c0b35ca7e8a}, \ref{f-cf08e451396b}, \ref{f-eeb9533cac7e}, \ref{f-bd4b2db75bf1}, \ref{f-222be326559e} and~\ref{f-7f1baefa4989}. 

A{\tt\string\ \unskip} 1498 (N=N), 3421.72(OH) , 3062.96-3014.74(C-H , aromatic) , 1618.28 (C=C), 1224.16-1203.58 (C-O), 1147.65 (C-N). 

S\ensuremath{_{1}}{\tt\string\ \unskip}max 1683.86 (C=N), 1502.55 (N=N) , 3061.03 -3030.17 (-CH,aromatic), 3414.00-3406.29(OH), 1618.28 (C=C) , 1355.96(CH3). 

S\ensuremath{_{2}}{\tt\string\ \unskip} max 1683.86 (C=N), 1500.62 (N=N) , 3066.82 -32972.31 (-CH,aromatic), 3458.37-3437.15 (OH), 1620.21 (C=C) , 1357.89 (CH3). 

S\ensuremath{_{3}}{\tt\string\ \unskip} max 1689.64 (C=N), 1581.63 (N=N), 3099.61 -3062.96 (-CH,aromatic), 3439.08-3360.00(OH), 1641.42 (C=C), 1355.96 (CH3). 

L\ensuremath{_{1}}{\tt\string\ \unskip} max 1712.79 (Lactone C=O), 1685.79-1658.78 (C=O ester and amide), 3061.03 to 2922. 16 (C-H,aromatic), 1600.92-1581.63 (C=C,aromatic ),1398.39 and 1361.74 (O-C-O and {\textendash}N-C-), 1168.86 (C-O). 

L\ensuremath{_{2}}{\tt\string\ \unskip}max 1718.58(Lactone C=O),1681.93 and 1624.06 (C=O ester and amide),3088.03 to 2922.16(C-H, aromatic), 1593.20-1519.91(C=C,aromatic).\textbf{\space }

L\ensuremath{_{3}}{\tt\string\ \unskip} max 1712.79(Lactone C=O),1681.93 and 1618.28 (C=O ester and amide),3059.10 to 3028.24(C-H, aromatic), 1587.42-1556.55(C=C,aromatic). 

L\ensuremath{_{4}}{\tt\string\ \unskip} max 1712.79(Lactone C=O),1639.49 and 1616.35 (C=O ester and amide),3064.89 to 2987.74(C-H, aromatic), 1589.34(C=C,aromatic). 

L\ensuremath{_{5}}{\tt\string\ \unskip} max 1681(Lactone C=O),1618.28 (C=O ester and amide),3062.96 to 3018.60(C-H, aromatic), 1568.13-1552.70(C=C,aromatic). 

L\ensuremath{_{6}}{\tt\string\ \unskip} max 1720.50(Lactone C=O),1681.93 and 1618.28 (C=O ester and amide),3064.89 to 3014.74(C-H, aromatic), 1589.34-1568.13(C=C,aromatic. 


\bgroup
\fixFloatSize{images/1a8d8902-c8a8-47aa-985c-48f7ef1c7930-upicture1.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/1a8d8902-c8a8-47aa-985c-48f7ef1c7930-upicture1.png}{\includegraphics{images/1a8d8902-c8a8-47aa-985c-48f7ef1c7930-upicture1.png}}{}
\makeatother 
\caption{1-(3-((2- hydroxynaphthalen-1-yl)diazenyl)acetophenone (A) and 1-((3-(1-((3 nitrophenyl)imino)ethyl)phenyl)diazenyl)naphthalen-2-ol (S2)}
\label{f-7c0b35ca7e8a}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/e5b7d146-f0cb-4dd4-9702-0849bece7814-upicture2.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/e5b7d146-f0cb-4dd4-9702-0849bece7814-upicture2.png}{\includegraphics{images/e5b7d146-f0cb-4dd4-9702-0849bece7814-upicture2.png}}{}
\makeatother 
\caption{\boldmath {1-((3-(1-((4-hydroxyphenyl)imino)ethyl)phenyl)diazenyl)naphthalen-2-ol(S1) and 1-((3-(1-(p-tolylimino)ethyl)phenyl)diazenyl)naphthalen-2-ol (S3)}}
\label{f-cf08e451396b}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/201a94aa-32cf-41d9-95e3-11af480c1964-upicture3.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/201a94aa-32cf-41d9-95e3-11af480c1964-upicture3.png}{\includegraphics{images/201a94aa-32cf-41d9-95e3-11af480c1964-upicture3.png}}{}
\makeatother 
\caption{\boldmath {2-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-3-(4-hydroxyphenyl)-2-methyl-1,3-oxazepane-4,7-dione(L1) and3-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-3-methyl-4-(3-nitrophenyl)-3,4-dihydrobenzo[e][1,3]oxazepine-1,5-dione (L5)}}
\label{f-eeb9533cac7e}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/505a3be7-26b2-4f80-b968-7612e398f755-upicture4.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/505a3be7-26b2-4f80-b968-7612e398f755-upicture4.png}{\includegraphics{images/505a3be7-26b2-4f80-b968-7612e398f755-upicture4.png}}{}
\makeatother 
\caption{\boldmath {2-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-2-methyl-3-(3-nitrophenyl)-1,3-oxazepane-4,7-dione(L2) and3-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-3-methyl-4-(p-tolyl)-3,4-dihydrobenzo[e][1,3]oxazepine-1,5-dione(L6)}}
\label{f-bd4b2db75bf1}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/21a90f05-fff1-4e50-8bed-47add0f42b3e-upicture5.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/21a90f05-fff1-4e50-8bed-47add0f42b3e-upicture5.png}{\includegraphics{images/21a90f05-fff1-4e50-8bed-47add0f42b3e-upicture5.png}}{}
\makeatother 
\caption{\boldmath {2-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-2-methyl-3-(p-tolyl)-1,3-oxazepane-4,7-dione (L3)}}
\label{f-222be326559e}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/a5557810-4fd6-43ac-8077-0be10379e33b-upicture6.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/a5557810-4fd6-43ac-8077-0be10379e33b-upicture6.png}{\includegraphics{images/a5557810-4fd6-43ac-8077-0be10379e33b-upicture6.png}}{}
\makeatother 
\caption{\boldmath {3-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-4-(4-hydroxyphenyl)-3-methyl-3,4-dihydrobenzo[e][1,3]oxazepine-1,5-dione (L4)}}
\label{f-7f1baefa4989}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/6a1aba4a-b478-4ff5-b544-e96bb90f25c9-upicture7.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/6a1aba4a-b478-4ff5-b544-e96bb90f25c9-upicture7.png}{\includegraphics{images/6a1aba4a-b478-4ff5-b544-e96bb90f25c9-upicture7.png}}{}
\makeatother 
\caption{\boldmath {1-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl) ethan-1-one (A) and 1-((3-(1-((4-hydroxyphenyl)imino)ethyl)phenyl)diazenyl)naphthalen-2-ol(S1)}}
\label{f-a4bdbf7df86c}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/cc351579-c1d1-4d5b-97c6-b156a2c38c66-upicture8.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/cc351579-c1d1-4d5b-97c6-b156a2c38c66-upicture8.png}{\includegraphics{images/cc351579-c1d1-4d5b-97c6-b156a2c38c66-upicture8.png}}{}
\makeatother 
\caption{\boldmath {1-((3-(1-((3-nitrophenyl)imino)ethyl)phenyl)diazenyl)naphthalen-2-ol(S2) and 2-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-2-methyl-3-(p-tolyl)-1,3-oxazepane-4,7-dione(L3)}}
\label{f-48ca01d736e2}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/64d09f4e-fb2a-4d64-a663-e663e6806f04-upicture9.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/64d09f4e-fb2a-4d64-a663-e663e6806f04-upicture9.png}{\includegraphics{images/64d09f4e-fb2a-4d64-a663-e663e6806f04-upicture9.png}}{}
\makeatother 
\caption{\boldmath {1-((3-(1-(p-tolylimino)ethyl)phenyl)diazenyl)naphthalen-2-ol(S3) and 3-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-4-(4-hydroxyphenyl)-3-methyl-3,4-dihydrobenzo[e][1,3]oxazepine-1,5-dione (L4)}}
\label{f-81f769f4e430}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/a296cd08-2ae3-4351-b825-4238ab873bee-upicture10.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/a296cd08-2ae3-4351-b825-4238ab873bee-upicture10.png}{\includegraphics{images/a296cd08-2ae3-4351-b825-4238ab873bee-upicture10.png}}{}
\makeatother 
\caption{\boldmath {2-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-3-(4-hydroxyphenyl)-2-methyl-1,3-oxazepane-4,7-dione(L1) and 3-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-3-methyl-4-(3-nitrophenyl)-3,4-dihydrobenzo[e][1,3]oxazepine-1,5-dione (L5)}}
\label{f-cbb9e73c3c2c}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/3763af8a-2a4b-4bfe-8e83-144b7c391c83-upicture11.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/3763af8a-2a4b-4bfe-8e83-144b7c391c83-upicture11.png}{\includegraphics{images/3763af8a-2a4b-4bfe-8e83-144b7c391c83-upicture11.png}}{}
\makeatother 
\caption{\boldmath {2-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-2-methyl-3-(3-nitrophenyl)-1,3-oxazepane-4,7-dione(L2) and3-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-3-methyl-4-(p-tolyl)-3,4-dihydrobenzo[e][1,3]oxazepine-1,5-dione(L6)}}
\label{f-8b67bc45ea27}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/9e16d952-324d-4d44-b4f3-f8c75a99973a-upicture12.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/9e16d952-324d-4d44-b4f3-f8c75a99973a-upicture12.png}{\includegraphics{images/9e16d952-324d-4d44-b4f3-f8c75a99973a-upicture12.png}}{}
\makeatother 
\caption{\boldmath {1-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl) ethan-1-one (A) and 1-((3-(1-((4-hydroxyphenyl)imino)ethyl)phenyl)diazenyl)naphthalen-2-ol(S1)}}
\label{f-4b9fd07fff54}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/3f296bbf-3a18-4cd5-8b29-5d236371e183-upicture13.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/3f296bbf-3a18-4cd5-8b29-5d236371e183-upicture13.png}{\includegraphics{images/3f296bbf-3a18-4cd5-8b29-5d236371e183-upicture13.png}}{}
\makeatother 
\caption{\boldmath {1-((3-(1-((3-nitrophenyl)imino)ethyl)phenyl)diazenyl)naphthalen-2-ol(S2) and 1-((3-(1-(p-tolylimino)ethyl)phenyl)diazenyl)naphthalen-2-ol (S3)}}
\label{f-1259627bbead}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/8c4df2d8-cc23-40bf-b494-ec5ef40d97f6-upicture14.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/8c4df2d8-cc23-40bf-b494-ec5ef40d97f6-upicture14.png}{\includegraphics{images/8c4df2d8-cc23-40bf-b494-ec5ef40d97f6-upicture14.png}}{}
\makeatother 
\caption{\boldmath {2-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-3-(4-hydroxyphenyl)-2-methyl-1,3-oxazepane-4,7-dione(L1) and3-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-3-methyl-4-(3-nitrophenyl)-3,4-dihydrobenzo[e][1,3]oxazepine-1,5-dione (L5) }}
\label{f-2e4f183ca1eb}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/56a07289-85fc-4023-9ac7-6e12f3bf69e0-upicture15.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/56a07289-85fc-4023-9ac7-6e12f3bf69e0-upicture15.png}{\includegraphics{images/56a07289-85fc-4023-9ac7-6e12f3bf69e0-upicture15.png}}{}
\makeatother 
\caption{\boldmath {2-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-2-methyl-3-(3-nitrophenyl)-1,3-oxazepane-4,7-dione(L2) and3-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-3-methyl-4-(p-tolyl)-3,4-dihydrobenzo[e][1,3]oxazepine-1,5-dione(L6)}}
\label{f-b71cdfe57380}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/deb46fec-b423-4737-9fe5-943160001a53-upicture16.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/deb46fec-b423-4737-9fe5-943160001a53-upicture16.png}{\includegraphics{images/deb46fec-b423-4737-9fe5-943160001a53-upicture16.png}}{}
\makeatother 
\caption{\boldmath {2-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-2-methyl-3-(p-tolyl)-1,3-oxazepane-4,7-dione(L3)}}
\label{f-01519cf09745}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/ed31eb91-ae4a-4255-8e91-4b4f9ac06810-upicture17.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/ed31eb91-ae4a-4255-8e91-4b4f9ac06810-upicture17.png}{\includegraphics{images/ed31eb91-ae4a-4255-8e91-4b4f9ac06810-upicture17.png}}{}
\makeatother 
\caption{\boldmath {3-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-4-(4-hydroxyphenyl)-3-methyl-3,4-dihydrobenzo[e][1,3]oxazepine-1,5-dione (L4)}}
\label{f-da2c7007681a}
\end{figure*}
\egroup
\ensuremath{^{\textbf{1}}} \textbf{HNMR- Spectra of derivatives }

Using DMSO as a solvent, \ensuremath{^{1}}HNMR- Spectra of derivatives are shown in Figures~\ref{f-a4bdbf7df86c}, \ref{f-48ca01d736e2}, \ref{f-81f769f4e430}, \ref{f-cbb9e73c3c2c} and~\ref{f-8b67bc45ea27}. 

A{\tt\string\ \unskip}Singlet 2.101 ppm(CH3),singlet 2.5 ppm (Dmso), multipleting singal at 6.996-7.377 ppm (phenol ring ), singlet 11.01ppm(OH).

S\ensuremath{_{1}}{\tt\string\ \unskip}Singlet 2.077ppm(CH3), 2.512 ppm(Dmso), multipleting singal at 6.998-7.643 ppm (phenal ring), 10.743-11-381 ppm (OH).

S\ensuremath{_{2}}{\tt\string\ \unskip}Singlet 2.064ppm(CH3), singlet 2.515ppm (Dmso), multipleting singal at 7.038-7.980 ppm (phenal ring),11.814 ppm (OH).

S\ensuremath{_{3}}{\tt\string\ \unskip}Singlet 1.718ppm-2.088ppm (CH3) , singlet 2.518ppm (Dmso) , multipleting singal at 7.401-8.498 ppm (phenal ring ) , single 11.518ppm (OH).

L\ensuremath{_{1}}{\tt\string\ \unskip}Singlet 2.018ppm (CH3), singlet 2.524 ppm (Dmso),doublet singnal at 6.849-6. 23ppm (CH=CH), multipleting signal at 7.536-8.392ppm(phenal ring) , singlet 10.818- 11.497ppm(OH).

L\ensuremath{_{2}}{\tt\string\ \unskip} Singlet 2.097ppm (CH3),singlet 2.523 ppm (Dmso),doublet singnal at 6.6-6.8ppm (CH=CH),multipleting signal at 7.717-8.159ppm(phenal ring), singlet 11.797ppm(OH).

L\ensuremath{_{3}}{\tt\string\ \unskip} Singlet 1.813-2.113ppm (CH3),singlet 2.522 ppm (Dmso),doublet singnal at 6.483-6.493ppm (CH=CH),multipleting signal at 7.152 {\textendash} 7.376ppm(phenal ring), singlet 11.028ppm(OH).

L\ensuremath{_{4}}{\tt\string\ \unskip}Singlet 2.019ppm(CH3), singlet 2.520 ppm (Dmso), multipleting signal 6.8 {\textendash} 7.8ppm(phenal ring), 10.135- 11.435ppm(OH).

L\ensuremath{_{5}}{\tt\string\ \unskip} Singlet 2.053ppm(CH3), singlet 2.520 ppm (Dmso), multipleting signal 7.036 {\textendash} 7.932 ppm(phenal ring), 11.728 ppm(OH). 

L\ensuremath{_{6}}{\tt\string\ \unskip} Singlet 1.534 - 2.084ppm(CH3, singlet 2.523 ppm (Dmso), multipleting signal 7.6-8.2 ppm(phenal ring), 11.584 ppm(OH).

\textbf{The C\ensuremath{^{13}}.NMR Spectral of derivatives }

Using DMSO as a Solvent, the C\ensuremath{^{13}}.NMR Spectrums of derivatives are shown in Figures~\ref{f-4b9fd07fff54}, \ref{f-1259627bbead}, \ref{f-2e4f183ca1eb}, \ref{f-b71cdfe57380}, \ref{f-01519cf09745} and~\ref{f-da2c7007681a}.

A{\tt\string\ \unskip}Singlet 26.36 ppm(CH3),197.52ppm(C=O), multipleting singal at 111.1-149.148 ppm (phenol ring), singlet 155. 1ppm(OH). 

S\ensuremath{_{1}}{\tt\string\ \unskip}Singlet273ppm(CH3), 159PPM (C=N),153-154 ppm (OH). 

S\ensuremath{_{2}}{\tt\string\ \unskip}Singlet 26.411(CH3), 159.054PPM(C=N),154 ppm (OH). 

S\ensuremath{_{3}}{\tt\string\ \unskip}Singlet 21.605-25605 (CH3), 159.432PPM, single153.442PPM (OH). 

L\ensuremath{_{1}}{\tt\string\ \unskip}Singlet 27.57PPM (CH3),160.7PPM (O-C-N), 172.57 {\textendash} 174.4 PPM (C=O), 163.7 PPM (HC=CH), 153.6-154.8ppm(OH). 

L\ensuremath{_{2}}{\tt\string\ \unskip} Singlet 25.63PPM (CH3),161.12PPM (O-C-N),172.77-173.56ppm(C=O) ,164.12PPM(HC=CH), 155.057ppm(OH). 

L{\tt\string\ \unskip} Singlet 24.827-27.116PPM (CH3),160.449PPM(O-C-N),173-175.2PPM(C=O),163.827PPM (CH=CH), singlet 154.474 PPM(OH)

L\ensuremath{_{4}}{\tt\string\ \unskip}Singlet26.46ppm(CH3),160.2PPM(O-C-N),174.6-175.1PPM(C=O),153.1-154.1ppm(OH). 

L\ensuremath{_{5}}{\tt\string\ \unskip}Singlet 26.5ppm(CH3),160.7PPM(O-C-N),172.4-173.9PPM(C=O),154.6ppm(OH).

L\ensuremath{_{6}}{\tt\string\ \unskip}Singlet26.6-22.2ppm(CH3),163PPM(O-C-N),171-175PPM(C=O),154.2ppm(OH).
    
\section{Conclusion}
This study presents a synthesis of innovative oxazepine derivatives by multi-reaction steps. The initial step synthesis azo derivative from 2-naphthol with 3-aminoacetophenone. The second step has been the condensation reacting between ketone group of the azo compound and diverse primary aromatic amines (4-amino phenol, 3-nitro aniline and 4-methyl aniline) to yiled new azo Schiff base compounds (S\ensuremath{_{1-}}S\ensuremath{_{3}}) respectively. In the last step, Oxazepine compounds (L\ensuremath{_{1-}}L\ensuremath{_{3}})and (L\ensuremath{_{4-}}L\ensuremath{_{6}}) have been organized by reacting imine compounds (S\ensuremath{_{1-}}S\ensuremath{_{3}}) with maleic and phthalic anhydride in toluene as solvent. All these derivatives have categorized by melting point, FTIR, HNMR and \ensuremath{^{13}}CNMR.
    

\bibliographystyle{pharmascope_apa-custom}

\bibliography{\jobname}
\end{document}
