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Dr.S.Alexandar,M.Pharm,Ph.D
Associate Professor
Vinayaka Missions College of Pharmacy
Yercaud main road
Kondappanaickanpatty
Salem, Tamilnadu
Pin:636008
Hetero cyclic Chemistry
QuinolinePyridine
2
3
Quinoline is a heterocyclic aromatic organic compound with the chemical formula
C9H7N. It is a colorless hygroscopic liquid with a strong odor .
Quinoline is only slightly soluble in cold water but dissolves readily in hot water and
most organic solvents. Quinoline itself has few application, but many of its
derivatives are useful in diverse applications. A prominent example is quinine, which is
found naturally in plants as alkaloids
Sources of quinoline include petroleum, coal processing, wood preservation,
production and use facilities, and shale oil.
Quinoline has been detected in tobacco smoke, emissions from petroleum refining, coal
and shale oil processing, and wood preservation.
4
Synthesis of Quinoline:
Skraup reaction:
The Skraup synthesis is a chemical reaction used to synthesize Quinolines. It is named
after the Czech chemist Zdenko Hans Skraup (1850-1910). Aniline is heated with
sulfuric acid, glycerol, and an oxidizing agent, like nitrobenzene to yield Quinoline.
5
CH2OH
CHOH
CH2OH
CH2
CH
C
OH
Glycerol Acroline
NH2
N
H
CH2
CH2
H
O
-H2O
N
H
C6H5NO2
Oxidation
-H2O
N
Acrolein obtained by dehydration of glycerol in presence of concentrated sulfuric acidis an
intermediate, which then undergoes 1,4-addition to form ß-phenyl aminopropionaldehyde .
Further dehydration of ß-phenyl Aminopropionaldehyde forms 1,2-Dihydro Quinoline.
1,2-Dihydro Quinoline converts Quinoline by oxidation with nitro benzene
1,2-Dihydro QuinolineQuinoline
6
Reaction of Quinoline:
1)Electrophilic substitution reaction:
It undergoes electrophilic substitution reaction in the benzene ring because benzene ring is
more reactive than a pyridine ring. Substitution takes place primarily at C-5 and C-8
5-Nitro Quinoline 8-Nitro Quinoline
Quinoline- 5- Sulphonic acid Quinoline- 8- Sulphonic acid
7
2) Nucleophilic substitution reaction:
Quinoline undergoes Nucleophilic aromatic substitution at C-2 and C-4 due to
the presence of pyridine ring
8
3) Reduction of Quinoline:
The pyridine ring is more easily reduced
 Quinoline can be selectively reduced at 1,2-bond by reaction with lithium
aluminum hydride but the 1,2-dihydroquinolines are unstable and disproportionate
easily to give Quinoline and 1,2,3,4-tetrahydroquinoline.
 Quinoline can be converted to 1,2,3,4-tetrahydroquinoline by catalytic
hydrogenation or with tin and hydrochloric acid
1,2,3,4-tetrahydroquinoline1,2-dihydro Quinolines
1,2,3,4-tetrahydroquinoline
9
4 ) Oxidation:
Quinoline undergo oxidative cleavage with alkaline potassiumpermangnate to give
pyridine-2,3-dicarboxylic acid
 However, pyridine-2,3-dicarboxylic acid is not stable and undergoes decarboxylation to
give nicotinic acid.
Pyridine-2,3-dicarboxylic acid Nicotinic acid
10
Applications of Quinoline:
Quinoline is used in the manufacture of dyes. Quinoline and Quinoline derivative can be
used in manufacturing a wide range of Food Colors, Lake Colors, Salt Free Dyes, etc. which
are extensively used as Dyes in various industries, such as Food, Pharmaceutical and
Cosmetic.
Medicinal compounds
Chloroquine – Treatment for malaria by interfering with DNA, it kills the erythrocytic
forms of malarial parasite at all developmental stages.
Primaquine - It is also an antimalarial drug.
Praziquante – it is used as an Anthelmentic drug
11
Aromaticity
Aromatic
It has 6 delocalized electrons
.
..
.
. .
Basicity
It has basic properties because the nitrogen lone pair
electrons are free and available for sharing as base
12
 Pyridine is a six membered heterocyclic compound with molecularPyridine is a six membered heterocyclic compound with molecular
formula of Cformula of C66HH55NN and it is obtained from coal tar.and it is obtained from coal tar.
 IIt may be formally derived from the structure of benzene throught may be formally derived from the structure of benzene through
the exchange of one ring carbon forthe exchange of one ring carbon for aa spsp2 hybridized nitrogen2 hybridized nitrogen aa
nitrogen.nitrogen.
 Pyridine isPyridine is an aromatic compound,an aromatic compound, however,however, thethe nitrogen’s lonenitrogen’s lone
pairpair of electronsof electrons is in an sp2 orbital orthogonal to the p orbitals of
the ring, therefore it is not involved in maintaining aromaticity bis not involved in maintaining aromaticity but
it is available to react with protons thus pyridine is basic
13
Hantzsch pyridine synthesis
It is a multi-component organic reaction between an
aldehyde such as formaldehyde, 2 equivalents of a β-
keto ester such as ethyl acetoacetate and a nitrogen
donor such as ammonium acetate or ammonia. The
initial reaction product is a dihydropyridine which can
be oxidized in a subsequent step to a pyridine. The
driving force for this second reaction step is
aromatization.
14
Synthesis of Pyridine
1-1- From 1,5-dicarbonyl compounds:From 1,5-dicarbonyl compounds:
O O
NH H
NH4OAc
15
2-2- Bönnemann cyclization:Bönnemann cyclization:
Synthesis of Pyridine
3-3- Hantzsch Synthesis:Hantzsch Synthesis:
O
OEt
O O
H H
OEt
O
O
++
N
H
EtO
O
OEt
O
HNO3
[O]
NH3
Ethylacetoacetate
-dicarbonyl cpd
dihydropyridine drivative 1) KOH
2) CaO, ∆
N
O O
N
EtO
O
OEt
O
β
N
CH
CH
+ NHC +
CH
CH
red hot tube
16
Synthesis of Pyridine
N
H
+ CHCl3
KOH
N
Cl
Pyrrole
C
N
+
N
CN CN - H2
N
CN
300 C°
1,3-butadiene
4-4- From pyrrole:From pyrrole:
5-5- By Diels Alder reactionBy Diels Alder reaction
17
Reactions of electrophilic substitution (SE).
The reactions of nitration, sulphonation and halogenation pass
slowly drastic and with low exits. Thus an electrophilic reagent is
direct in position 3.
3- Nithropyridine
Pyridine -3- Sulphonic acid
3-Bromo pyridine
18
19
 2- and 4-substituted (but not 3-substituted)
halopyridines readily undergo nucleophilic
aromatic substitution
1. Reduction .
2. Oxidization .
pyperedine
nicotinic acid
20
Compared to pyrrole, pyridine is much stronger baseCompared to pyrrole, pyridine is much stronger base this is due to
the nitrogen lone pair is not involved in maintaining the aromaticity
thus it free for protonation, however, in pyrrole the lone pair on the N
atom is already involved in the aromatic array of p electrons.
Protonation of pyrrole on N atom results in loss of aromaticity and is
therefore unfavorable. 
Compared to imidazole, pyridine is less basicCompared to imidazole, pyridine is less basic this is due to the onthis is due to the on
protonation the + ve charge can be delocalized over two nitrogen atomsprotonation the + ve charge can be delocalized over two nitrogen atoms
while in case of pyridine it is delocalized over the ring which interruptwhile in case of pyridine it is delocalized over the ring which interrupt
aromatcity.aromatcity.
21
22
Uses
 Used as solvent
 As a catalyst in many organic reactions
 For denaturing alcohol
 In the preparation of certain drugs
Medicinal compounds
Isoniazide – it is an anti tubercular drug and it is effective against pulmonary and extra
pulmonary tuberculosis
Nikethamide - It is used in the treatment of CNS depression caused by drugs. It is also used
as respiratory stimulant
Nicotinic acid – It is essential for the normal functioning of skin, Intestinal tract and
nervous system. It is available as biologically active amide derivative (Nicotinamide).
Benzhexol – it is used in the treatment of parkinsonism

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Heterocyclic Chemistry of Quinoline and Pyridine

  • 1. Dr.S.Alexandar,M.Pharm,Ph.D Associate Professor Vinayaka Missions College of Pharmacy Yercaud main road Kondappanaickanpatty Salem, Tamilnadu Pin:636008 Hetero cyclic Chemistry
  • 3. 3
  • 4. Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor . Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few application, but many of its derivatives are useful in diverse applications. A prominent example is quinine, which is found naturally in plants as alkaloids Sources of quinoline include petroleum, coal processing, wood preservation, production and use facilities, and shale oil. Quinoline has been detected in tobacco smoke, emissions from petroleum refining, coal and shale oil processing, and wood preservation. 4
  • 5. Synthesis of Quinoline: Skraup reaction: The Skraup synthesis is a chemical reaction used to synthesize Quinolines. It is named after the Czech chemist Zdenko Hans Skraup (1850-1910). Aniline is heated with sulfuric acid, glycerol, and an oxidizing agent, like nitrobenzene to yield Quinoline. 5
  • 6. CH2OH CHOH CH2OH CH2 CH C OH Glycerol Acroline NH2 N H CH2 CH2 H O -H2O N H C6H5NO2 Oxidation -H2O N Acrolein obtained by dehydration of glycerol in presence of concentrated sulfuric acidis an intermediate, which then undergoes 1,4-addition to form ß-phenyl aminopropionaldehyde . Further dehydration of ß-phenyl Aminopropionaldehyde forms 1,2-Dihydro Quinoline. 1,2-Dihydro Quinoline converts Quinoline by oxidation with nitro benzene 1,2-Dihydro QuinolineQuinoline 6
  • 7. Reaction of Quinoline: 1)Electrophilic substitution reaction: It undergoes electrophilic substitution reaction in the benzene ring because benzene ring is more reactive than a pyridine ring. Substitution takes place primarily at C-5 and C-8 5-Nitro Quinoline 8-Nitro Quinoline Quinoline- 5- Sulphonic acid Quinoline- 8- Sulphonic acid 7
  • 8. 2) Nucleophilic substitution reaction: Quinoline undergoes Nucleophilic aromatic substitution at C-2 and C-4 due to the presence of pyridine ring 8
  • 9. 3) Reduction of Quinoline: The pyridine ring is more easily reduced  Quinoline can be selectively reduced at 1,2-bond by reaction with lithium aluminum hydride but the 1,2-dihydroquinolines are unstable and disproportionate easily to give Quinoline and 1,2,3,4-tetrahydroquinoline.  Quinoline can be converted to 1,2,3,4-tetrahydroquinoline by catalytic hydrogenation or with tin and hydrochloric acid 1,2,3,4-tetrahydroquinoline1,2-dihydro Quinolines 1,2,3,4-tetrahydroquinoline 9
  • 10. 4 ) Oxidation: Quinoline undergo oxidative cleavage with alkaline potassiumpermangnate to give pyridine-2,3-dicarboxylic acid  However, pyridine-2,3-dicarboxylic acid is not stable and undergoes decarboxylation to give nicotinic acid. Pyridine-2,3-dicarboxylic acid Nicotinic acid 10
  • 11. Applications of Quinoline: Quinoline is used in the manufacture of dyes. Quinoline and Quinoline derivative can be used in manufacturing a wide range of Food Colors, Lake Colors, Salt Free Dyes, etc. which are extensively used as Dyes in various industries, such as Food, Pharmaceutical and Cosmetic. Medicinal compounds Chloroquine – Treatment for malaria by interfering with DNA, it kills the erythrocytic forms of malarial parasite at all developmental stages. Primaquine - It is also an antimalarial drug. Praziquante – it is used as an Anthelmentic drug 11
  • 12. Aromaticity Aromatic It has 6 delocalized electrons . .. . . . Basicity It has basic properties because the nitrogen lone pair electrons are free and available for sharing as base 12
  • 13.  Pyridine is a six membered heterocyclic compound with molecularPyridine is a six membered heterocyclic compound with molecular formula of Cformula of C66HH55NN and it is obtained from coal tar.and it is obtained from coal tar.  IIt may be formally derived from the structure of benzene throught may be formally derived from the structure of benzene through the exchange of one ring carbon forthe exchange of one ring carbon for aa spsp2 hybridized nitrogen2 hybridized nitrogen aa nitrogen.nitrogen.  Pyridine isPyridine is an aromatic compound,an aromatic compound, however,however, thethe nitrogen’s lonenitrogen’s lone pairpair of electronsof electrons is in an sp2 orbital orthogonal to the p orbitals of the ring, therefore it is not involved in maintaining aromaticity bis not involved in maintaining aromaticity but it is available to react with protons thus pyridine is basic 13
  • 14. Hantzsch pyridine synthesis It is a multi-component organic reaction between an aldehyde such as formaldehyde, 2 equivalents of a β- keto ester such as ethyl acetoacetate and a nitrogen donor such as ammonium acetate or ammonia. The initial reaction product is a dihydropyridine which can be oxidized in a subsequent step to a pyridine. The driving force for this second reaction step is aromatization. 14
  • 15. Synthesis of Pyridine 1-1- From 1,5-dicarbonyl compounds:From 1,5-dicarbonyl compounds: O O NH H NH4OAc 15
  • 16. 2-2- Bönnemann cyclization:Bönnemann cyclization: Synthesis of Pyridine 3-3- Hantzsch Synthesis:Hantzsch Synthesis: O OEt O O H H OEt O O ++ N H EtO O OEt O HNO3 [O] NH3 Ethylacetoacetate -dicarbonyl cpd dihydropyridine drivative 1) KOH 2) CaO, ∆ N O O N EtO O OEt O β N CH CH + NHC + CH CH red hot tube 16
  • 17. Synthesis of Pyridine N H + CHCl3 KOH N Cl Pyrrole C N + N CN CN - H2 N CN 300 C° 1,3-butadiene 4-4- From pyrrole:From pyrrole: 5-5- By Diels Alder reactionBy Diels Alder reaction 17
  • 18. Reactions of electrophilic substitution (SE). The reactions of nitration, sulphonation and halogenation pass slowly drastic and with low exits. Thus an electrophilic reagent is direct in position 3. 3- Nithropyridine Pyridine -3- Sulphonic acid 3-Bromo pyridine 18
  • 19. 19  2- and 4-substituted (but not 3-substituted) halopyridines readily undergo nucleophilic aromatic substitution
  • 20. 1. Reduction . 2. Oxidization . pyperedine nicotinic acid 20
  • 21. Compared to pyrrole, pyridine is much stronger baseCompared to pyrrole, pyridine is much stronger base this is due to the nitrogen lone pair is not involved in maintaining the aromaticity thus it free for protonation, however, in pyrrole the lone pair on the N atom is already involved in the aromatic array of p electrons. Protonation of pyrrole on N atom results in loss of aromaticity and is therefore unfavorable.  Compared to imidazole, pyridine is less basicCompared to imidazole, pyridine is less basic this is due to the onthis is due to the on protonation the + ve charge can be delocalized over two nitrogen atomsprotonation the + ve charge can be delocalized over two nitrogen atoms while in case of pyridine it is delocalized over the ring which interruptwhile in case of pyridine it is delocalized over the ring which interrupt aromatcity.aromatcity. 21
  • 22. 22 Uses  Used as solvent  As a catalyst in many organic reactions  For denaturing alcohol  In the preparation of certain drugs Medicinal compounds Isoniazide – it is an anti tubercular drug and it is effective against pulmonary and extra pulmonary tuberculosis Nikethamide - It is used in the treatment of CNS depression caused by drugs. It is also used as respiratory stimulant Nicotinic acid – It is essential for the normal functioning of skin, Intestinal tract and nervous system. It is available as biologically active amide derivative (Nicotinamide). Benzhexol – it is used in the treatment of parkinsonism