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

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Heterocyclic and Pericyclic Chemistry Mapa Mental sobre Know the main synthesis and selected reactions of imidazoles, oxazoles and thiazoles, creado por al44 el 05/12/2013.
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Mapa Mental por al44, actualizado hace más de 1 año
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Creado por al44 hace alrededor de 11 años
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Know the main synthesis and selected reactions of imidazoles, oxazoles and thiazoles
  1. Imidazoles
    1. Synthesis
      1. dihaloketone, amine and amide
        1. 175oC
          1. -2EtOH, -HCl, -H2O
        2. Reactivity
          1. Highly basic
            1. Protonation gives resonance
              1. Stabilised symmetrical cation
                1. 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
                    1. Nucleophilic substitution
                      1. RONu and acid imidazole
            2. Oxazoles
              1. Synthesis
                1. Fischer oxazole
                  1. cyanohydrin and aldehyde
                    1. HCl, ether
                  2. Robinson Gabriel synthesis
                    1. Dehydration of 2-acylamino-ketone
                  3. Reactivity
                    1. Electrophilic aromatic subsitution
                      1. Need EDG to activate
                        1. 5 position
                        2. Diels Alder
                          1. Followed by retro diels alder with loss of nitrile
                            1. Furan
                          2. Oxidation
                            1. Nucleophilic aromatic subsitution
                              1. Leaving group at C2
                          3. 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
                                      1. Requires activating group
                                      2. Diels Alder
                                        1. Extrusion of sulphur to form pyridine
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