BENZO CONDENSED PYRIDINES:

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BENZO CONDENSED PYRIDINES QUINOLINES AND
ISOQUINOLINES
Alkaloid Natural Products

• Largets class of secondary metabolites, gt6500
  compds known
• Contains N, most compds basic (alkaline), often
  heterocyclic
• Often highly toxic
• Found in certain higher plants (seldom in
  bacteria)
• Little is known regarding why alkaloids are
  produced
• Biosynthesis from amino acids

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Cinchona pubescens (Kinatre) from South America
Quinoline alkaloids
ROMe Quinine (Cinchonidine epimer at C-9) RH
Quinidine (Cinchonine epimer at C-9)
Quinidine Antiarytmic Quinine Antimalaria
Dihydroquini(di)ne and der. Chiral ligands Asym.
dihydroxylation (Sharpless)
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Isoquinoline alkaloids
Curare - Pilgift - Søramerikanske
indianere Bland. Av flere alkaloider med
muskeslammende effekt Flere plantekilder bl.a.
Chondodendron tomentosum
Ex. Mivacurium klorid Muscle relax, anesthesia
Suksametonium, Curacit Nesset
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Isoquinoline alkaloids
Noskapin (not analgetic, not adiction)
Morfinanalogs, binds to opiopeptide (endorfin /
enkefalin) reseptors
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Electrophilic Ar. Subst.
Protonation
Halogenation in the Pyridine Ring
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Nucleophilic Addition - Nucleophilic Ar. Subst.
Nu-radicals (Minisci react.) attacks in the same
pos.
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ANRORC (Add. Of Nu., Ring Opening and Ring
Closure)
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Oxy- and Aminoderivatives - Tautomeri
-All - isomers amino (not imino) -One-Isomers
Tautomeric Mixt.
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Synthesis - Quinolines
Synthesis - Isoquinolines