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
A novel heterocyclization of 1-acetylenyl-9,10-anthraquinones. / Shvartsberg, M. S.; Ivanchikova, I. D.; Vasilevsky, S. F.
In: Russian Chemical Bulletin, Vol. 47, No. 10, 01.01.1998, p. 1971-1974.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A novel heterocyclization of 1-acetylenyl-9,10-anthraquinones
AU - Shvartsberg, M. S.
AU - Ivanchikova, I. D.
AU - Vasilevsky, S. F.
PY - 1998/1/1
Y1 - 1998/1/1
N2 - 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.
AB - 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.
KW - 1-acetylenyl-9,10-anthraquinones
KW - 4H-anthra[9,1-cd]-1,2-diazepin-8-ones
KW - 7H-dibenzo[de,h]quinolin-7-ones
KW - Contraction of the seven-membered heterocycle
KW - Cyclocondensation
KW - Hydrazine
UR - http://www.scopus.com/inward/record.url?scp=0032280510&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0032280510&partnerID=8YFLogxK
U2 - 10.1007/BF02494508
DO - 10.1007/BF02494508
M3 - Article
AN - SCOPUS:0032280510
VL - 47
SP - 1971
EP - 1974
JO - Russian Chemical Bulletin
JF - Russian Chemical Bulletin
SN - 1066-5285
IS - 10
ER -