A novel heterocyclization of 1-acetylenyl-9,10-anthraquinones

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	https://doi.org/10.1007/BF02494508
Publication status	Published - 1 Jan 1998
Externally published	Yes

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)

Access to Document

10.1007/BF02494508

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title = "A novel heterocyclization of 1-acetylenyl-9,10-anthraquinones",

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. ",

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",

author = "Shvartsberg, {M. S.} and Ivanchikova, {I. D.} and Vasilevsky, {S. F.}",

year = "1998",

month = jan,

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doi = "10.1007/BF02494508",

language = "English",

volume = "47",

pages = "1971--1974",

journal = "Russian Chemical Bulletin",

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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

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