Azaanthracene
quinoline.svg) 1-Azaanthracene | |
isoquinoline.svg) 2-Azaanthracene | |
 9-Azaanthracene | |
| Names | |
|---|---|
| Other names
benzo[g]quinoline | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
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| Properties | |
| C13H9N | |
| Molar mass | 179.222 g·mol−1 |
| Melting point |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Azaanthracenes are organic compounds containing an anthracene moiety where one CH group has been replaced by nitrogen.[1] Thus, the parents have the formula C13NH7, vs C14H8 for anthracene itself. Three constitutional isomers are possible, depending on the location of N in the ring system. The isomer with the N in the central ring, variously identified as either 9-azaanthracene or 10-azaanthracene, is more commonly called acridine. The other two isomers are 1-azaanthracene and 2-azaanthracene. All three are solids at room temperature.
The azaanthracene framework can be formed by a condensation reaction to form the central ring from a precursor that contains the two side rings, among other routes. 1-Azaanthracene is the product from 2-benzyl-3-formylpyridine.[2] 2-Azaanthracene is the product from 4-benzyl-3-formylpyridine.[3] 9-Azaanthracene is the product from the Bernthsen acridine synthesis, using a mixture of diphenylamine and formic acid.
Azaanthracene-derived alkaloids have been characterized in nature, e.g. the cleistopholines.[4]
References
[edit]- ↑ Taniya, Olga S.; Kopchuk, Dmitry S.; Khasanov, Albert F.; Kovalev, Igor S.; Zyryanov, Grigory V.; Charushin, Valery N.; Chupakhin, Oleg N. (2019). "2-Azaanthracene (Microreview)". Chemistry of Heterocyclic Compounds. 55 (6): 505–507. doi:10.1007/s10593-019-02491-9.
- ↑ Krapcho, A. Paul; Gilmor, Timothy P. (1999). "General preparative route to benzo[g]quinolines (1-azaanthracenes)". Journal of Heterocyclic Chemistry. 36 (2): 445–452. doi:10.1002/jhet.5570360218.
- ↑ Krapcho, A. Paul; Gilmor, Timothy P. (1998). "General synthetic route to benz[g]isoquinolines (2-azaanthracenes)". Journal of Heterocyclic Chemistry. 35 (3): 669–674. doi:10.1002/jhet.5570350328.
- ↑ Chaves, Mariana H.; Santos, Luciana de A.; Lago, João Henrique G.; Roque, Nidia F. (2001). "Alkaloids from Porcelia macrocarpa". Journal of Natural Products. 64 (2): 240–242. doi:10.1021/np000373d. PMID 11434318.