Benzimidazolinone is an organic compound with the formula . Also classified as a heterocyclic compound it is a bicyclic urea. It is a tautomer of 2-hydroxybenzimidazole.
Synthesis, structure, applications
The parent compound is prepared by the carbonylation of 1,2-diaminobenzene. The carbonylation can be effected with carbonyldiimidazole. Like other ureas, it engages in hydrogen bonding, yielding supramolecular structures.
Benzimidazolinones Although the parent compound is of little interest per se, many derivatives are useful. Benzimidazolinone dyes Substituted 2-benzimidazolinones are commercial dyes and pigments. For example 4-amino-2-benzimidazolinone condenses with diketene to give the acetoacetanilide, which undergoes diazo coupling with various aryldiazonium salts. In this way pigment orange 36 and pigment yellow 154 are produced. These pigments are used in paints and plastics.
The structures of the azo-dyes has been determined by X-ray crystallography. Structurally related benzimidazolone pigments include Pigment Red 175, Pigment Red 176, Pigment Violet 32, and Pigment Brown 25.
Drugs Domperidone, an antiemetic Benperidol, an antipsychotic Sumanirole: A selective D2 receptor full agonist developed for Parkinson's disease. Sumanirole, for treatment of Parkinson's disease Droperidol, a sedative Flibanserin, for treatment of hypoactive disorders
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