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Heterocyclic Rings Pyridne, quinoline and isoquinoline

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Presentation on theme: "Heterocyclic Rings Pyridne, quinoline and isoquinoline"— Presentation transcript:

1 Heterocyclic Rings Pyridne, quinoline and isoquinoline

2 Pyridne Pyridine is a water -miscible liquid, b. p. 115 oC with an unpleasant odour An 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.

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4 1) The Hantzsch Synthesis 1,3-dicarbonyl compound + ammonia + aldehyde

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6 2) Reaction of Ammonia + 1,5-diketone

7 3) Diels-Alder Reaction

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11 4) Kroehnke Synthesis

12 Chemistry of Pyridine

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14 Electrophilic Substitution Pyridine is million times less reactive than benzene Nitration (less than 5%, Chlorination in moderate yield, Bromination in a good yield) 3-position is usually attacked preferably

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16 ChiChibabin Reaction (Nucleophilic Substitution)

17 Quinoline and Isoquinoline

18 Quinoline Skraup Synthesis

19 Combes Synthesis

20 Isoquinoline Synthesis, Bischler-Napierlaski

21 Pictet-Spengler Synthesis

22 Pomeranz-Fritsch Synthysis

23 Chemistry of Quinoline and Isoquinoline Nucleophilic Substitution (ChiChibabin Reaction)

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26 Electrophilic Substitution Occurs at the 5- or 8-positions, or both

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


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