Synthesis of 5, 6, 7, 8-Tetrahydroquinolines by Thermolysis of Oxime O-Allyl Ethers in the Presence of Boron Trifluoride Etherate
Thermolysis of cyclohexanone oxime O-crotyl and O-cinnamyl ether in the presence of BF3-etherate regioselectively gave 4-methyl- and 4-phenyl-5, 6, 7, 8-tetrahydroquinoline, while the addition of organic bases such as triethylamine and pyridine inhibited the rearrangement. These findings suggested t...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1993/07/15, Vol.41(7), pp.1297-1298 |
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| container_issue | 7 |
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| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 41 |
| creator | KOYAMA, Junko OGURA, Tamaki TAGAHARA, Kiyoshi MIYASHITA, Masaaki IRIE, Hiroshi |
| description | Thermolysis of cyclohexanone oxime O-crotyl and O-cinnamyl ether in the presence of BF3-etherate regioselectively gave 4-methyl- and 4-phenyl-5, 6, 7, 8-tetrahydroquinoline, while the addition of organic bases such as triethylamine and pyridine inhibited the rearrangement. These findings suggested that the addition of the acid made [1, 2] shift the predominant one of the two possible transformations, [1, 2] and [2, 3] shift, of the O-allyl ethers. |
| doi_str_mv | 10.1248/cpb.41.1297 |
| format | Article |
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Pharm. Bull.</addtitle><date>1993</date><risdate>1993</risdate><volume>41</volume><issue>7</issue><spage>1297</spage><epage>1298</epage><pages>1297-1298</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Thermolysis of cyclohexanone oxime O-crotyl and O-cinnamyl ether in the presence of BF3-etherate regioselectively gave 4-methyl- and 4-phenyl-5, 6, 7, 8-tetrahydroquinoline, while the addition of organic bases such as triethylamine and pyridine inhibited the rearrangement. These findings suggested that the addition of the acid made [1, 2] shift the predominant one of the two possible transformations, [1, 2] and [2, 3] shift, of the O-allyl ethers.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.41.1297</doi><tpages>2</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 1993/07/15, Vol.41(7), pp.1297-1298 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | J-STAGE Free; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | 4-methyl-5, 6, 7, 8-tetrahydroquinoline 4-phenyl-5, 6, 7, 8-tetrahydroquinoline 6, 7-dimethoxyonychine Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry oxime O-cinnamyl ether oxime O-crotyl ether Preparations and properties thermal rearrangement |
| title | Synthesis of 5, 6, 7, 8-Tetrahydroquinolines by Thermolysis of Oxime O-Allyl Ethers in the Presence of Boron Trifluoride Etherate |
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