Superelectrophilic Activation of 8-Hydroxyquinoline in Acid Media and Its Reactions with Weak Nucleophiles Full article
| Journal |
Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393 |
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| Output data | Year: 2002, Volume: 38, Number: 3, Pages: 437-442 Pages count : 6 DOI: 10.1023/A:1016306814374 | ||
| Tags | 11 hydroxy 6,11 dihydro 6,11 methano 5h benzo[5,6]cyclohepta[1,2 b]pyridine; benzene; bromide; chloride; cyclohexane; nitrogen; pyridine derivative; quinolinol derivative; unclassified drug | ||
| Authors |
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| Affiliations |
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Funding (2)
| 1 | The Ministry of Education and Science of the Russian Federation | A 0051 |
| 2 | The Ministry of Education and Science of the Russian Federation | 1.20.00 |
Abstract:
According to the H-1 and C-13 NMR data, 5-azonia-4-hydroxynaphthalen-1-onium cation, generated by protonation of 8-hydroxyquinoline in the system CF3SO3H-SbF5, reacts with cyclohexane to give diprotonated 5,6,7,8-tetrahydroquinolin-8-one. Further reaction of the latter with cyclohexane yields 5,6,7,8-tetrahydroquinolinium ion. The reaction of 8-hydroxyquinoline with benzene in the presence of aluminum bromide or chloride gives 6-phenyl-5,6,7,8-tetrahydroquinolin-8-one and product of its intramolecular cyclization, 11-hydroxy-6,11-dihydro-6,11-methano-5H-benzo[5,6]cyclohepta[1,2-b]pyridine. The effect of the protonated nitrogen atom on the electrophilicity of dications is discussed.
Cite:
Koltunov K.Y.
, Repinskaya I.B.
Superelectrophilic Activation of 8-Hydroxyquinoline in Acid Media and Its Reactions with Weak Nucleophiles
Russian Journal of Organic Chemistry. 2002. V.38. N3. P.437-442. DOI: 10.1023/A:1016306814374 WOS Scopus РИНЦ ANCAN OpenAlex
Superelectrophilic Activation of 8-Hydroxyquinoline in Acid Media and Its Reactions with Weak Nucleophiles
Russian Journal of Organic Chemistry. 2002. V.38. N3. P.437-442. DOI: 10.1023/A:1016306814374 WOS Scopus РИНЦ ANCAN OpenAlex
Original:
Колтунов К.Ю.
, Репинская И.Б.
Суперэлектрофильная активация 8-гидроксихинолина в кислых средах и его взаимодействие со слабыми нуклеофилами
Журнал органической химии. 2002. Т.38. №3. С.457-463.
Суперэлектрофильная активация 8-гидроксихинолина в кислых средах и его взаимодействие со слабыми нуклеофилами
Журнал органической химии. 2002. Т.38. №3. С.457-463.
Dates:
| Submitted: | Jun 14, 2001 |
| Published print: | Mar 1, 2002 |
Identifiers:
| Web of science: | WOS:000177064900022 |
| Scopus: | 2-s2.0-0012181218 |
| Elibrary: | 13390084 |
| Chemical Abstracts: | 2002:543329 |
| Chemical Abstracts (print): | 137:384491 |
| OpenAlex: | W2950378674 |