




































                               American International Journal of Multidisciplinary Scientific Research; Vol. 2, No. 1; 2018 

ISSN 2638-1249  E-ISSN 2638-1273 

Impact Factor: 5.8 

Published by Centre for Research on Islamic Banking & Finance and Business, USA 

 

 

1 
 

Cyclization of Multi Components Reactions and (Preparation, 

Investigation, Thermal Curves) 

 

Nagham Mahmood Aljamali
1
 , Nour Abd Alrazzak Abd Allattif

2
 &  Sabreen Ali Abdalrahman

3 

 

 

 
1
Department of Chemistry, Faculty of Education for Girls, Kufa University, Iraq 

2
Department of Chemistry, College of Science for Women, University of Babylon, Iraq 

3
B.Sc  in  Chemistry , Kufa  University , Iraq 

 

 

Correspondence: Dr. Nagham Mahmood Aljamali. Department of Chemistry, Faculty of Education for Girls, Kufa 

University, Iraq. Email: Dr.Nagham_mj@yahoo.com 

 

          

 

Received: August 29, 2018        Accepted: September 23, 2018               Online Published: October 10, 2018   

     DOI: 10.54655/aijmsr.v2n1p1 

 

 

Abstract 

Many  cyclic  compounds were  formatted  via  multi  components  reactions and cyclization  reaction  through  

many  steps  with ( various   conditions , various  starting  materials , various  components ), in  first  step , aromatic 

amine derivative  were  reacted  with  ammonium thiocyanate  in cyclization  reaction   to  yield  2-

aminobenzothiazole derivative , which  reacted  with  formaldehyde  and  benzaldehyde  as  a multi components   

reaction ., then  the  resulting  compounds  cyclized  with ( semicarbazide , ortho-phenyl diamine , ortho-thiol 

aniline , ortho- amino phenol ). Investigation  of  compounds   carried out   through  many  techniques ( FT.IR , 

H.NMR , Mass ) – Spectra  , Thermal  studies  

 

 

Keywords: Multi Components , Cyclization, Heterocyclic ,Oxadiazole, Imidazole, Thiazole, Oxazole. 

 

Introduction 

A heterocyclic compounds are a cyclic compound which have at least two different elements or more as members of 

its structure. Heterocyclic chemistry is the branch of  synthetic  chemistry dealing with the  preparation
(1-3) 

, 

characterization ,uses
(4-6)

, applications
(7-9)

 of these  compounds   that include all of the nucleic acids, drugs, cellulose  

and many natural and  industrial  dyes
(10-12)

. 

https://en.wikipedia.org/wiki/Cyclic_compound
https://en.wikipedia.org/wiki/Chemical_element
https://en.wikipedia.org/wiki/Organic_chemistry


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Fig.(1): Heterocycle  compounds  as  a drugs 

 

Heterocyclic derivatives have a wide range of  uses
(13-15)

  and  applications
(16-19) 

 in  pharmaceutical  chemistry
(20-

24)
,which  involved  many

(25-28)
 of the biochemical material essential to  bio- molecules  like  vitamins ,nucleic acids, 

the chemical  materials
(29-31)

 that carry the genetic information controlling inheritance, include  a long chains of 

heterocyclic units held together by other types
(32-36)

 of  substances . Many naturally occurring dyes , 

pigments, vitamins, and antibiotics are heterocyclic compounds
(37-40)

. 

 

Fig.(2): Heterocyclic  compound  as  a dye 

Experimental   Part    

Allcompounds  were  investigation    through  : FT-IR spectra (FT-IR 8300 Shimadzu) in the range (400-4000) cm
-1

 

asKBr  discs ., 1H.NMR– Spectra in DMSO–solvent., Mass  spectra, thermal   studying , solubility  test , physical  

properties : 

Procedures 

Synthesis   of Compounds {1 , 2 } 

p-Amino benzoic acid (0.1mole) reacted with ammonium thiocyanate (0.1mole) with (7 ml )  of (Br2) drop  by  drop 

with (5ml )  of  glacial  acetic  acid with  rotation for (3hrs) at (10 C˚)according to  literatures
(21 ,23)

,the  resulting  

compound (0.2 mole) reacted with (0.1 m0le) of  formaldehyde  with rotation  for (4 hrs )  in acid medium (3 ml )  

(HCl   or   H2SO4) to give  compound{ 1 }.,which  dissolved  in  ( 5 %  NaOH)  solution  then reacted with  furfural   

at  room  temperature  and  rotation  for  ( 5  hrs )  , then  filtered , dried  and re crystallized from ethanol  to yield  

compound { 2 }. 

https://www.britannica.com/science/nucleic-acid
https://www.britannica.com/technology/pigment
https://www.britannica.com/science/vitamin
https://www.britannica.com/science/antibiotic


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Scheme.1: Synthesis of Compounds { 1 , 2} 

Synthesis  of  Compounds{ 3- 5}: 

Compound { 2 }(0.01mole) refluxed  with  ethanol  and (3 ml) (H2SO4) for (2 hrs ) to give  compound {3} as  ester , 

which (0.1 mole )  refluxed  with (0.2 mole ) of  2-aminothiazole  for (2 hrs ) in ethanol  as a solvent  , then filtered , 

dried  and re crystallized from ethanol  to yield  compound { 4 }., while  compound { 2} (0.1 mole )  refluxed  with 

(0.2 mole ) of  2-mercaptothiazole  for (3 hrs ) in ethanol  as a solvent according  to procedures
(38, 40)

 , then filtered , 

dried  and re crystallized from ethanol  to yield  compound { 5 }. 

Scheme.2: Synthesis of Compounds { 3 - 5} 



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Synthesis   of  Compounds{ 6 , 7 }: 

Diethyl malonate (0.2 mole ) dissolved  in  base medium   then  refluxed  with  (0.1 mole ) of diethylsuccinatewith  

ethanol  for (2 hrs ) to give  compound {6} as  ester , which (0.1 mole )  refluxed  with (0.2 mole ) of  semicarbazide   

for (13 hrs ) in ethanol  as a solvent  and (3 ml of  H2SO4 )according  to procedures
(21, 23)

, then filtered , dried  and re 

crystallized from ethanol  to yield  compound { 7 }. 

Synthesis   of Compounds{ 8 - 10 }: 

Compound { 6} (0.1 mole )  refluxed  with (0.4mole ) of  ortho-phenyl diamine  for (7hrs ) with ( 4 N  of  HCl ) , 

then filtered , dried  and re crystallized from ethanol  to yield  compound { 8 }., while  compound { 6} (0.1 mole)  

refluxed  with (0.4 mole ) of  ortho-thiol aniline  for (9 hrs ) with ( 4 N  of  HCl ) , then filtered , dried  and re 

crystallized from ethanol  to yield  compound { 9 }.,compound { 6} (0.1 mole )  refluxed  with (0.4 mole ) of  ortho-

hydroxy aniline  for (9hrs ) with ( 4 N  of  HCl ) according  to procedures
(21, 23) 

, then filtered , dried  and re 

crystallized from ethanol  to yield  compound { 10 }., 

 

Scheme.3: Synthesis of Compounds { 6- 10} 

Results    and     Discussion  

Our  compounds characterized  with many  spectral  methods  like (FT.IR ,H.NMR ,Mass)   spectra  and      with  

thermal  studies: 



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Spectral  Investigation 

 FT.IR-  Spectra of  Compounds:It  appeared  many  absorption   bands appeared  at  (C=N) Endocycle: 1641., (C-

S) endocycle of  benzothiazole  : 734 ., (-CO-O-) carbonyl of carboxyl group : 1719 ., (NH)Amine group :3270 ., 

(OH) hydroxyl  of  carboxyl  group: 3120 in compound { 1} , while  other  bands   appeared at (C=N) Endocycle: 

1649., (C-S) endocycle of  benzothiazole  : 728 ., (-CO-O-) carbonyl of carboxyl group : 1714 ., (NH)Amine group 

:3276 .,(OH) hydroxyl  of  carboxyl  group: 3135 ., (CH=C ): 3100in compound {2}  ., other  bands   appeared at   

(C=N) Endocycle: 1650., (C-S) endocycle of  benzothiazole  : 717 ., (-CO-O-) carbonyl of  ester  group : 1722 ., 

(NH)Amine group :3262  ., (CH=C ): 3097in compound { 3 }., but   compound {4} appeared  bands  at  (C=N) 

Endocycle: 1643., (C-S) endocycle of  benzothiazole  : 729 ., (NH)Amine group :3273  ., (CH=C ): 3096  ., (-NH-

CO) amine  of  amide : 3204 ., (CO-N) carbonyl  of amide : 1689 .,  while  compound { 5}  gave  bands  at  (C=N) 

Endocycle: 1637., (C-S) endocycle of  benzothiazole  : 711 ., (NH)Amine group :3264  ., (CH=C ): 3104  .,(CO-S) 

carbonyl : 1694  ., other  bands  at  (-CO-O-) carbonyl of  ester  group : 1724 .,(-CO-CH2-) carbonyl of  ketone : 

1708 ., (CH- ) aliphatic : 2967  in  compound {6} ,  the  spectrum  of  compound { 7} appeared  bands  at  (-CO-

CH2-) carbonyl of  ketone : 1713 ., (CH- ) aliphatic : 2985 ., (NH2) amine group: (3245 , 3266 ) .,(C=N) Endocycle  

of  oxadiazole: 1663 .,  but  bands  at (-CO-CH2-) carbonyl of  ketone : 1711 ., (CH- ) aliphatic : 2918 ., (NH) amine 

: 3210  .,(C=N) Endocycle  of  imidazole: 1656   due  to  compound {8 } ., while   appearance  of  bands  at  (-CO-

CH2-) carbonyl of  ketone : 1709 ., (CH- ) aliphatic : 2923 .,(C=N) Endocycle  of  thiazole: 1642 ., (C-S) endocycle 

of  benzothiazole : 753  due  to  compound { 9} ., the  compound  {10} gave  bands  at  (-CO-CH2-) carbonyl of  

ketone : 1716 ., (CH- ) aliphatic : 2900 .,(C=N) Endocycle  of  oxazole: 1642 .,all bands  abstracted   in Table (1) . 

Table (1): FT.IR- data (cm
-1

) of Compounds { 1-10 } 

Compounds  Other  Groups 

 

{ 1 } (C=N) Endocycle: 1641., (C-S)endocycle of  benzothiazole  : 734 ., (-CO-O-) carbonyl of 

carboxyl group : 1719 ., (NH)Amine group :3270 .,  

(OH) hydroxyl of carboxyl  group: 3120 . 

{ 2 } (C=N) Endocycle: 1649., (C-S) endocycle of  benzothiazole  : 728 ., (-CO-O-) carbonyl of 

carboxyl group : 1714 ., (NH)Amine group :3276 .,  

(OH) hydroxyl  of  carboxyl  group: 3135 ., (CH=C ): 3100  . 

{ 3 } (C=N) Endocycle: 1650., (C-S) endocycle of  benzothiazole  : 717 ., (-CO-O-) carbonyl of  

ester  group : 1722 ., (NH)Amine group :3262  ., (CH=C ): 3097  . 

{4}  (C=N) Endocycle: 1643., (C-S) endocycle of  benzothiazole  : 729 ., (NH)Amine group 

:3273  ., (CH=C ): 3096  ., (-NH-CO) amine  of  amide : 3204 ., (CO-N) carbonyl  of 

amide : 1689 .  

{5} (C=N) Endocycle: 1637., (C-S) endocycle of  benzothiazole  : 711 ., (NH)Amine group 

:3264  ., (CH=C ): 3104  .,(CO-S) carbonyl : 1694 . 

{6} (-CO-O-) carbonyl of  ester  group : 1724 .,(-CO-CH2-) carbonyl of  ketone : 1708 ., (CH- 

) aliphatic : 2967 . 

{7} (-CO-CH2-) carbonyl of  ketone : 1713 ., (CH- ) aliphatic : 2985 ., (NH2) amine group: 

(3245 , 3266 ) .,(C=N) Endocycle  of  oxadiazole: 1663 . 

{8} (-CO-CH2-) carbonyl of  ketone : 1711 ., (CH- ) aliphatic : 2918 ., (NH) amine : 3210  

.,(C=N) Endocycle  of  imidazole: 1656 . 

{9} (-CO-CH2-) carbonyl of  ketone : 1709 ., (CH- ) aliphatic : 2923 .,(C=N) Endocycle  of  

thiazole: 1642 ., (C-S) endocycle of  benzothiazole : 753. 

{10} (-CO-CH2-) carbonyl of  ketone : 1716 ., (CH- ) aliphatic : 2900 .,(C=N) Endocycle  of  

oxazole: 1642 . 

 
1
H.NMR- Spectra of Compounds 

It  appeared   peaks at ƃ DMSO-d6(solvent ): 2.50  ., (N-CH2-N-) Protons : 1.92  ., (NH-): 5.12 ., Protons  of   

Phenyl ring : (6.84-7.89)., (-COOH)proton of carboxyl  group  of  acid : 13.42  in  compound { 1 } ., while  it  gave  

signals  at(NH-): 5.32 ., Protons  of   Phenyl ring : (6.67-7.99)., (-COOH)proton of carboxyl  group  of  acid : 13.26  

., (C=CH) :2.41  in  compound  { 2 } ., (., (NH-): 5.48 ., Protons  of   Phenyl ring : (6.84-7.72)., (-COO-Eth)protons 

of ethyl  group :(3.03 , 3.27 )  ., (C=CH) :2.29  in  compound { 3} .,(NH-): 5.31 ., Protons  of   Phenyl ring  and  

heterocycles: (6.96-7.64)., (-CO-NH)proton of  amide  group :10.03  ., (C=CH) :2.10  in  compound {4} ., (NH-): 

5.62 ., Protons  of   Phenyl ring  and  heterocycles: (6.75-7.83)   ., (C=CH) :2.19  in  compound {5} ., (CO-CH2-



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CH2-CO) : (2.00 , 2.09 , 2.25) ., (COOEth ): ( 3.05 – 3.37 )  in  compound { 6} .,(CO-CH2-CH2-CO): (2.08 , 2.11 , 

2.19) ., (NH2) : 5.67   in  compound { 7} ., (CO-CH2-CH2-CO) : (2.06 , 2.17 , 2.29) ., (NH) : 5.23  ., Protons  of   

Phenyl ring : (6.96-7.64)  in  compound { 8} .,(CO-CH2-CH2-CO) : (2.13 , 2.18 , 2.21) .,Protons  of   Phenyl ring : 

(6.80-7.52)  in  compound { 9} .,  (CO-CH2-CH2-CO) : (2.09 , 2.17 , 2.24) .,Protons  of   Phenyl ring : (6.98-7.87)  

in  compound { 10}  which  give (CO-CH2-CH2-CO) : (2.09 , 2.17 , 2.24) .,Protons  of   Phenyl ring : (6.98-7.87). 

evidences  for  preparation  of  our  compounds ., and other  peaks   abstracted  in table (2)  

  Table (2): H.NMR-data (ƃ - ppm) of   Compounds{ 1 – 10 } 

Compounds  Other   groups 

{ 1 } DMSO-d6(solvent ): 2.50  ., (N-CH2-N-) Protons : 1.92  ., (NH-): 5.12 ., Protons  of   Phenyl 

ring : (6.84-7.89)., (-COOH)proton of carboxyl  group  of  acid : 13.42  . 

{ 2 } DMSO-d6(solvent ): 2.50 ., (NH-): 5.32 ., Protons  of   Phenyl ring : (6.67-7.99)., (-

COOH)proton of carboxyl  group  of  acid : 13.26  ., (C=CH) :2.41  . 

{ 3 } DMSO-d6(solvent ): 2.50 ., (NH-): 5.48 ., Protons  of   Phenyl ring : (6.84-7.72)., (-COO-

Eth)protons of ethyl  group :(3.03 , 3.27 )  ., (C=CH) :2.29 . 

{4} DMSO-d6(solvent ): 2.50 ., (NH-): 5.31 ., Protons  of   Phenyl ring  and  heterocycles: (6.96-

7.64)., (-CO-NH)proton of  amide  group :10.03  ., (C=CH) :2.10 . 

{5} DMSO-d6(solvent ): 2.50 ., (NH-): 5.62 ., Protons  of   Phenyl ring  and  heterocycles: (6.75-

7.83)   ., (C=CH) :2.19 . 

{6} DMSO-d6(solvent ): 2.50  ., (CO-CH2-CH2-CO) : (2.00 , 2.09 , 2.25) ., (COOEth ): ( 3.05 – 

3.37 ).  

{7} DMSO-d6(solvent ): 2.50  .,(CO-CH2-CH2-CO): (2.08 , 2.11 , 2.19) ., (NH2) : 5.67 . 

{8} DMSO-d6(solvent ): 2.50  ., (CO-CH2-CH2-CO) : (2.06 , 2.17 , 2.29) ., (NH) : 5.23  ., 

Protons  of   Phenyl ring : (6.96-7.64). 

{9} DMSO-d6(solvent ): 2.50  ., (CO-CH2-CH2-CO) : (2.13 , 2.18 , 2.21) .,Protons  of   Phenyl 

ring : (6.80-7.52). 

{10} DMSO-d6(solvent ): 2.50  ., (CO-CH2-CH2-CO) : (2.09 , 2.17 , 2.24) .,Protons  of   Phenyl 

ring : (6.98-7.87). 

 

The  Mass  Spectra of  Compounds 
There  spectra  showed  good  results  for  formatted  compounds  and  appeared  good  evidence   for  their   

fragments  in  figures(3-5): 

 

Fig(3): Mass  Spectra of  Compound { 5 } 



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Fig(4): Mass  Spectra of  Compound { 8} 

 

Fig(5): Mass  Spectra of  Compound{ 10} 

Thermal – Curves  of   Compounds  

The  compounds studied  through thermal  analysis which  appeared stability against  different   temperatures in  

figures (6- 10)  : 

 

Fig (6) : Thermal  Curve   of    Compound{4} 



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Fig 

(7) : Thermal  Curve   of    Compound{5} 

 

Fig (8) : Thermal  Curve   of    Compound{8} 

 

Fig (9) : Thermal  Curve   of    Compound{9} 



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Fig 

(10): Thermal  Curve  of    Compound{10} 

Solubility of Compounds in Organic Solvents 

Test  of  the solubility  of compounds  screened  with  several  organic  solvents  according to (type  of  solvent , 

polarity  of solvents ,  activity  of  functional  groups) in  compounds, the  results abstracted    in Table (3). 

 

 Table (3) : Behavior  of  compounds   in Solvents   

Compounds Solvents 

C2H5OH Methanol  Chloroform Acetone Benzene  Toluene  

( 1 ) + + - - - - 

( 2 ) + + - - - - 

( 3 ) + + - - - - 

( 4 ) + + - - - - 

( 5 ) + + - - - - 

( 6 ) + + - - - - 

( 7 ) + + - - - - 

( 8 ) + + - - - - 

( 9 ) + + - - - - 

( 10 ) + + - - - - 

 

Physical and Chemical Properties of Compound {1 – 10 }   

The  Results  In  Table (4) Appeared   Properties  And  Characterization Like: [(Rf)  Of  TLC- Technique For  

Following  The   Reactions  ,Type Of  Solvent  Which Was  Used  In  TLC – Plate , Yield  From  Reactions % ], 

All   Data  Are  Abstracted   In  Table (4):  

 



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Table(4): Some Physical  and Chemical  Properties  for  compounds {1 – 10 }   

Compounds  Yield  % Rf Solvents   of    (TLC) 

( 1:2) 

( 1 ) 72 0.4 Ethanol : Benzene 

( 2 ) 70 0.70 Ethanol : Benzene 

( 3 ) 64 0.70 Ethanol : Benzene 

( 4 ) 78 0.70 Ethanol : Benzene 

( 5 ) 74 0.68 Ethanol : Benzene 

( 6 ) 68 0.66 Ethanol : Benzene 

( 7 ) 70 0.70 Ethanol : Benzene 

( 8 ) 74 0.62 Ethanol : Benzene 

( 9 ) 72 068 Ethanol : Benzene 

( 10 ) 76 0.64 Ethanol : Benzene 

 

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37. EmanH. S .,Nagham Mahmood Aljamali .,"New Azo-Thiadiazole Ligands (Preparation, Spectral, Thermal, 

Biochemical, Physical properties) - Studying " .,Journal of Global Pharma Technology. 2017; 11, 9 ,165. 

38.Mieaad Mohamd , Nagham Mahmood Aljamali , Nadheema Abed Abbas ., " Preparation, Spectral Investigation, 

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of Global Pharmacy Technology, 2018; 10, 1, 20-29. 

39. Intisar ObaidA , Eman HS , Nagham Mahmood Aljamali ., "Synthesis of (Tetrazole,  Oxazepine, Azo, Imine) 

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https://en.wikipedia.org/wiki/Digital_object_identifier
https://dx.doi.org/10.1016%2Fj.tet.2005.08.031
https://en.wikipedia.org/wiki/Digital_object_identifier
https://dx.doi.org/10.1039%2FB701677H
http://dx.doi.org/10.5958/0974-360X.2015.00016.5


www.cribfb.com/journal/index.php/aijmsr           American International Journal of Multidisciplinary Scientific Research           Vol. 2, No. 1; 2018 

 
 

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40. Mieaad Mohamd , Nagham Mahmood Aljamali , Wassan AlaShubber , Sabreen Ali Abdalrahman .," New 

Azomethine- Azo Heterocyclic Ligands Via Cyclization of Ester " ., Research J. Pharm. and Tech. 11, 6 , 

2018 .,DOI: 10.5958/0974-360X.2018.00472.9  . 

 

 

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