Gogte, V. N. ; Salama, M. A. ; Tilak, B. D. (1970) Synthesis of nitrogen heterocyclics- VI: Stereochemistry of hydride transfer in acid-catalysed disproportionation of 3,4-disubstituted 1,2-dihydroquinolines Tetrahedron, 26 (1). pp. 173-181. ISSN 0040-4020
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Official URL: http://www.sciencedirect.com/science/article/pii/0...
Related URL: http://dx.doi.org/10.1016/0040-4020(70)85017-7
Abstract
Acid catalysed disproportionation of 7-methoxy-1,3,4-trimethyl-1,2-dihydroquinoline (VI) gave 65% cis-isomer (VII) and 35% trans-isomer (VIII) of 7-methoxy-1,3,4-trimethyl-1,2,3,4-tetrahydroquinoline by intermolecular hydride transfer. Disproportionation of 1,3-dimethyl-7-methoxy-4-phenyl-1,2-dihydroquinoline (IX) and 3-methoxy-5-methyl-5,6,7,8,9,10-hexahydrophenanthridine (XII) likewise gave a mixture of the corresponding cis- and trans-derivatives in similar proportions. In contrast disproportionation of 4,5-dihydro-7-methoxy-5-methylcyclopenteno(c)quinoline (XX) gave almost exclusively the relevant cis-tetrahydrocyclopentano(c)quinoline (XXII).
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 53641 |
| Deposited On: | 09 Aug 2011 11:29 |
| Last Modified: | 09 Aug 2011 11:29 |
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