Reactions of 2-, 3- and 4-Quinolinols with Cyclohexane and Benzene in Superacids Full article
| Journal |
Heterocycles
ISSN: 0385-5414 , E-ISSN: 1881-0942 |
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| Output data | Year: 2004, Volume: 62, Pages: 757-772 Pages count : 16 DOI: 10.3987/COM-03-S(P)74 | ||
| Tags | 3 quinolinol; 4 quinolinol; aluminum chloride; aluminum derivative; benzene; carbostyril; cyclohexane; quinolinol derivative; unclassified drug | ||
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Abstract:
Isomeric 2-, 3- and 4-quinolinols (11-13) underwent selective ionic hydrogenation with cyclohexane in CF3SO3H-SbF5 system to give 5,6,7,8-tetrahydro-2(1H)-quinolinone, 5,6,7,8-tetrahydro-3-quinolinol and 5,6,7,8-tetrahydro-4(1H)-quinolinone (28-30), respectively. When reaction was carried out in the presence of excess of aluminum chloride, 11 gave 3,4-dihydro-2(1H)-quinolinone (31), whereas 13 gave the product (30). Compounds (11) and (13) condense with benzene in the presence of aluminum halides producing phenyl substituted derivatives of 28, 31 and 30 (products 32-34), respectively. The mechanism of these and related reactions involving superelectrophilic dicationic intermediates is discussed.
Cite:
Koltunov K.Y.
, Prakash G.K.S.
, Rasul G.
, Olah G.A.
Reactions of 2-, 3- and 4-Quinolinols with Cyclohexane and Benzene in Superacids
Heterocycles. 2004. V.62. P.757-772. DOI: 10.3987/COM-03-S(P)74 WOS Scopus РИНЦ ANCAN OpenAlex
Reactions of 2-, 3- and 4-Quinolinols with Cyclohexane and Benzene in Superacids
Heterocycles. 2004. V.62. P.757-772. DOI: 10.3987/COM-03-S(P)74 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
| Submitted: | Oct 6, 2003 |
| Accepted: | Nov 13, 2003 |
| Published online: | Nov 18, 2003 |
Identifiers:
| Web of science: | WOS:000188256600060 |
| Scopus: | 2-s2.0-0347720665 |
| Elibrary: | 14382404 |
| Chemical Abstracts: | 2004:15263 |
| Chemical Abstracts (print): | 140:163688 |
| OpenAlex: | W2038748504 |