Reactions of Quinolines and Isoquinolines Flashcards

1
Q

selective reduction of nitrogen ring

A

uses H2/Pt, 2atm and water

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2
Q

Ring oxidation

A

using Pd/C and MeCN at 100C oxidises to aromatic ring

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3
Q

N-oxide formation

A

quinoline and m-CPBA

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4
Q

reduction of N-oxides

A

using PCl3 gives quinoline, driving force is formation of PO bond

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5
Q

EAS of quinoline n-oxides

A

substitution at quinoline C4, most resonance forms

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6
Q

Installing Cl leaving group in quinoline

A

N-oxide and POCl3 adds Cl at C2 position

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7
Q

Installing Cl leaving group in isoquinoline

A

N-oxide and POCl3 adds Cl at C1 to preserve aromativiet

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8
Q

Conversion to iso/quinolone

A

N-oxide with Ac2O and heat then NaOH

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9
Q

EAS

A

substitution at electron rich benzene, more wheland intermediates, more stable and more aromaticity preserved

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10
Q

side chain chemistry

A

C2 and C4 quinoline side chains are acidic and can be deprotonated

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11
Q

selective reduction of benzene ring

A

H2/Pt, 3 atm and conc H+

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