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Please login to access the full content or check if you have access via28.10.3.1.2.1.3 Variation 3: Condensation of Phenanthrene-9,10-diones with Iminohydrazides, Sulfanamide, Thiosemicarbazide, Semicarbazide, or Aminoguanidines
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Avendaño, C.; Menéndez, J. C., Science of Synthesis, (2006) 28, 790.
The reaction between phenanthrene-9,10-dione and 3-nitrobenzimidic acid hydrazide gives the fused 1,2,4-triazine 189.[148] Similarly, treatment of the same dione with sulfanamide in the presence of an acid gives the fused 1,2,5-thiadiazole 1,1-dioxide 190 (Scheme 65).[149] This last product and its analogues are useful since pyrolysis gives aromatic dinitriles (e.g., 2,2′-biphenyldicarbonitrile is obtained by heating 190).[150] On the other hand, treatment of phenanthrene-9,10-diones with semicarbazide or thiosemicarbazide can be controlled to give the corresponding (thio)semicarbazones (single condensation) or phenanthrene-fused triazines (double condensation). For instance, the dibromophenanthrenequinone 191 gives the tricyclic compound 192.[151] Aminoguanidines also condense with phenanthrene-9,10-diones in the presence of an acid to give fused 1,2,4-triazines such as 193 (Scheme 65).[151] However, phenanthrene-9,10-dione and semicarbazide hydrochloride in the presence of acetic acid react to give the monosemicarbazone 194 (Scheme 65).[152]
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8,88-Meeeeeeeeeeeeeeee[8,88-e][8,8,8]eeeeeee-8-eeeee Meeeeeeeeeeee (888):[888]
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Meeeeeeeeeee-8,88-eeeee Meeeeeeeeeeeeeeee (888):[888]
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References
| [148] | Meeee, M.; Meeeeee, M. M.; Meeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
| [149] | Meeeeeeeee, M. M.; Meeeeee, M., Meeeeee. Meee., (8888) 88, 888. |
| [150] | Mee, M.; Meeeeeeee, M., Meeeeeeee, (8888), 88. |
| [151] | Meeeeee, M.; Müeeeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
| [152] | Meeee, M. M.; Meeeeeee, M.; Meeeeeeeeee, M. M., Meeeeeeeeee, (8888) 88, 888. |
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