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Know the main synthesis and selected reactions of imidazoles, oxazoles and thiazoles

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Heterocyclic and Pericyclic Chemistry Mind Map on Know the main synthesis and selected reactions of imidazoles, oxazoles and thiazoles, created by al44 on 05/12/2013.

Mind Map by al44, updated more than 1 year ago

	Created by al44 almost 11 years ago

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Resource summary

Know the main synthesis and selected reactions of imidazoles, oxazoles and thiazoles

Imidazoles
1. Synthesis
  1. dihaloketone, amine and amide
    1. 175oC
    2. -2EtOH, -HCl, -H2O
2. Reactivity
  1. Highly basic
    1. Protonation gives resonance
      1. Stabilised symmetrical cation
      2. Commonly used to form silyl ethers
  2. Formation of acid imidazolides
    1. Staab reagent, two imidazoles connected by carbonyl
      1. Imidazozole attached to carbonyl group on nitrogen + formation of imidazole and carbon dioxide
        Nucleophilic substitution
        RONu and acid imidazole
Oxazoles
1. Synthesis
  1. Fischer oxazole
    1. cyanohydrin and aldehyde
      1. HCl, ether
  2. Robinson Gabriel synthesis
    1. Dehydration of 2-acylamino-ketone
2. Reactivity
  1. Electrophilic aromatic subsitution
    1. Need EDG to activate
    2. 5 position
  2. Diels Alder
    1. Followed by retro diels alder with loss of nitrile
      1. Furan
  3. Oxidation
  4. Nucleophilic aromatic subsitution
    1. Leaving group at C2
Thiazoles
1. Synthesis
  1. Hantzsch thiazole
    1. Haloketone and thioamide
      1. Methanol, R.T, 3 hrs
2. Reactivity
  1. Deprotection at C2
    1. -ve charge stabilised as ylide
      1. Organolithium reacts at site replacing proton
  2. Electrophilic aromatic substitution
    1. At C5
    2. Requires activating group
  3. Diels Alder
    1. Extrusion of sulphur to form pyridine

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