Abstract
1-Acetylenyl-9,10-anthraquinones react with an excess of NH 2 NH 2 at 80-115°C to give a mixture of substituted 7H-dibenzo[de,h]quinolin-7-ones and anthra[9, 1-cd]-1,2-diazepin-8-ones. The latter compounds undergo reductive contraction of the seven-membered ring to give the corresponding 7H-dibenzo[de,h]quinolin-7-ones. Bulky substituents in position 2 of the initial acetylenylanthraquinones prevent the formation of the seven-membered heterocycle. A scheme of the cyclocondensation was proposed.
| Original language | English |
|---|---|
| Pages (from-to) | 1971-1974 |
| Number of pages | 4 |
| Journal | Russian Chemical Bulletin |
| Volume | 47 |
| Issue number | 10 |
| DOIs | |
| Publication status | Published - 1 Jan 1998 |
| Externally published | Yes |
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Keywords
- 1-acetylenyl-9,10-anthraquinones
- 4H-anthra[9,1-cd]-1,2-diazepin-8-ones
- 7H-dibenzo[de,h]quinolin-7-ones
- Contraction of the seven-membered heterocycle
- Cyclocondensation
- Hydrazine
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Shvartsberg, M. S., Ivanchikova, I. D., & Vasilevsky, S. F. (1998). A novel heterocyclization of 1-acetylenyl-9,10-anthraquinones. Russian Chemical Bulletin, 47(10), 1971-1974. https://doi.org/10.1007/BF02494508