Azaanthracenes are organic compounds containing an anthracene moiety where one CH group has been replaced by nitrogen. Thus, the parents have the formula 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-Azaanthracene is the product from 4-benzyl-3-formylpyridine. 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.
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