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Heterocyclic Heterocyclic

Heterocyclic - PowerPoint Presentation

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Uploaded On 2016-06-25

Heterocyclic - PPT Presentation

Rings Pyridne quinoline and isoquinoline Pyridne Pyridine is a water miscible liquid b p 115 oC with an unpleasant odour An Excelent polar solvent A base ID: 377303

quinoline synthesis isoquinoline reaction synthesis quinoline reaction isoquinoline pyridine position yield ammonia chichibabin nucleophilic electrophilic substitution pyridne chemistry pyrrole

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Slide1

Heterocyclic Rings Pyridne, quinoline and isoquinolineSlide2

PyridnePyridine is a water -miscible liquid, b. p. 115 oC with an unpleasant odourAn Excelent polar solvent, A base (

pka

= 5.23

)Pyrrole is less basic than pyridine becuase the lone pair of electrons in pyrrole is part of the aromatic ring, while that in pyridine is free.Slide3
Slide4

1) The Hantzsch Synthesis1,3-dicarbonyl compound + ammonia + aldehydeSlide5
Slide6

2) Reaction of Ammonia + 1,5-diketoneSlide7

3) Diels-Alder ReactionSlide8
Slide9
Slide10
Slide11

4) Kroehnke SynthesisSlide12

Chemistry of PyridineSlide13
Slide14

Electrophilic SubstitutionPyridine is million times less reactive than benzeneNitration (less than 5%, Chlorination in moderate yield, Bromination in a good yield)3-position is usually attacked preferablySlide15
Slide16

ChiChibabin Reaction (Nucleophilic Substitution) Slide17

Quinoline and IsoquinolineSlide18

Quinoline Skraup SynthesisSlide19

Combes SynthesisSlide20

Isoquinoline Synthesis, Bischler-NapierlaskiSlide21

Pictet-Spengler SynthesisSlide22

Pomeranz-Fritsch SynthysisSlide23

Chemistry of Quinoline and Isoquinoline Nucleophilic Substitution (ChiChibabin Reaction)Slide24
Slide25
Slide26

Electrophilic SubstitutionOccurs at the 5- or 8-positions, or bothSlide27

Quinoline N-Oxides can be nitrated at the 4-position or photoisomerize as follows