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Oxazoles, imidazoles, and thiazoles
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This chapter examines oxazoles, imidazoles, and thiazoles. Oxazole, imidazole, and thiazole are the parent structures of a related series of 1,3-azoles containing a nitrogen atom plus a second heteroatom in a five-membered ring. They are isomeric with the 1,2-azoles isoxazole, pyrazole, and isothiazole, and their aromaticity derives from delocalization of a lone pair from the second heteroatom. Oxazole, imidazole, and thiazole can be formally derived from furan, pyrrole, and thiophene respectively by replacement of a CH group by a nitrogen atom at the 3 position. The presence of this pyridine-like nitrogen deactivates the 1,3-azoles towards electrophilic attack and increases their susceptibility towards nucleophilic attack. The chapter then looks at the synthesis, electrophilic substitution reactions, anion chemistry, and nucleophilic aromatic substitution of oxazoles, imidazoles, and thiazoles.
Title: Oxazoles, imidazoles, and thiazoles
Description:
This chapter examines oxazoles, imidazoles, and thiazoles.
Oxazole, imidazole, and thiazole are the parent structures of a related series of 1,3-azoles containing a nitrogen atom plus a second heteroatom in a five-membered ring.
They are isomeric with the 1,2-azoles isoxazole, pyrazole, and isothiazole, and their aromaticity derives from delocalization of a lone pair from the second heteroatom.
Oxazole, imidazole, and thiazole can be formally derived from furan, pyrrole, and thiophene respectively by replacement of a CH group by a nitrogen atom at the 3 position.
The presence of this pyridine-like nitrogen deactivates the 1,3-azoles towards electrophilic attack and increases their susceptibility towards nucleophilic attack.
The chapter then looks at the synthesis, electrophilic substitution reactions, anion chemistry, and nucleophilic aromatic substitution of oxazoles, imidazoles, and thiazoles.
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