Azole

An azole is a type of organic compound. Azoles have a pentagon-shaped ring of five atoms. Azoles have two double bonds, like cyclopentadiene, and have at least one nitrogen atom.

Azole is the systematic name of pyrrole, the simplest azole. Its analogs are called pyrroles. Other azoles can have a second heteroatom, which can be chalcogen (oxygen, sulfur, selenium, or tellurium) or more nitrogen. 

 Types 
Azoles are grouped by the type of heteroatom in the ring.
 Type  Second heteroatom  Example  Example structure Pyrroles  None  Pyrrole  80px Oxazoles  Oxygen Oxazole  80px Isoxazole  80px Thiazoles  Sulfur Thiazole  80px Isothiazole  80px Imidazoles  Nitrogen Imidazole  80px Pyrazole  80px

There are also selenazoles and tellurazoles, containing selenium and tellurium. These molecules are much less common and do not have notable applications.

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