Chemistry:Benzimidazolinone
Benzimidazolinone is an organic compound with the formula C
6H
4(NH)
2CO. 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.[1] 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.[2][3]
The structures of the azo-dyes has been determined by X-ray crystallography.[4] 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
- Droperido, a sedative
- Flibanserin, for treatment of hypoactive disorders
References
- ↑ Schwiebert, Kathryn E.; Chin, Donovan N.; MacDonald, John C.; Whitesides, George M. (1996). "Engineering the Solid State with 2-Benzimidazolones". Journal of the American Chemical Society 118 (17): 4018–4029. doi:10.1021/ja952836l.
- ↑ Jaffe, Edward E. (2004). "Pigments, Organic". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.151807011001060605.a01.pub2. ISBN 978-0-471-48494-3.
- ↑ Hans-Joachim Metz, Frank Morgenroth (2009). "Benzimidazolone Pigments and Related Structures". in Edwin B. Faulkner, Russell J. Schwartz. High Performance Pigments. John Wiley & Sons. p. 135. ISBN 978-3-527-62692-2. https://books.google.com/books?id=ecD6AuaJyFwC.
- ↑ Van De Streek, Jacco; Brüning, Jürgen; Ivashevskaya, Svetlana N.; Ermrich, Martin; Paulus, Erich F.; Bolte, Michael; Schmidt, Martin U. (2009). "Structures of six industrial benzimidazolone pigments from laboratory powder diffraction data". Acta Crystallographica Section B Structural Science 65 (2): 200–211. doi:10.1107/S0108768108041529. PMID 19299876.
 |  |
