Indazole
Indazole, also called isoindazole, is a heterocyclic aromatic organic compound. This bicyclic compound consists of the fusion of benzene and pyrazole.
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| IUPAC name
1H-indazole | |||
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3D model (JSmol) |
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| ECHA InfoCard | 100.005.436 | ||
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| Properties | |||
| C7H6N2 | |||
| Molar mass | 118.14 g/mol | ||
| Melting point | 147 to 149 °C (297 to 300 °F; 420 to 422 K) | ||
| Boiling point | 270 °C (518 °F; 543 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
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Indazole derivatives display a broad variety of biological activities.
Indazoles are rare in nature. The alkaloids nigellicine, nigeglanine, and nigellidine are indazoles. Nigellicine was isolated from the widely distributed plant Nigella sativa L. (black cumin). Nigeglanine was isolated from extracts of Nigella glandulifera.
The Davis–Beirut reaction can generate 2H-indazoles.
Indazole, C7H6N2, was obtained by E. Fischer (Ann. 1883, 221, p. 280) by heating ortho-hydrazine cinnamic acid,[1]
C6H4 | CH = CH·COOH | =C2H4O2+C7H6N2. |
| NH·NH2 |
Some derivatives
- indazole-3-carboxylic acid
Having a carboxylic acid group on carbon 3. Can be further modified to lonidamine & tolnidamine.
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See also
- Indole, an analog with only one nitrogen atom in position 1.
- Benzimidazole, an analog with the nitrogen atoms in positions 1 and 3.
- Simple aromatic rings
- 7-Nitroindazole, an indazole-based nitric oxide synthase inhibitor
References
- Chisholm, Hugh, ed. (1911). . Encyclopædia Britannica. 14 (11th ed.). Cambridge University Press. p. 371.
- Synthesis: W. Stadlbauer, in Science of Synthesis 2002, 12, 227, and W. Stadlbauer, in Houben-Weyl, 1994, E8b, 764.
- Review: A. Schmidt, A. Beutler, B. Snovydovych, Recent Advances in the Chemistry of Indazoles, Eur. J. Org. Chem. 2008, 4073 – 4095.
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