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- Title
A (1,3) Strain in cis- and trans-5, 6-dihydro-4, 6-dimethyl-4 H, 8 H-pyrido [3,2,1- de]phenanthridin-8-ones.
- Authors
Nagarajan, Kuppuswamy; Shah, Rashmi K.; Fuhrer, Hermann; Puckett, Reginal T.; Narasimhamurthy, Mathur R.; Venkatesan, Kailasam
- Abstract
The stereochemistry of trans- and cis-2, 4-dimethyl-tetrahydroquinolines, 6 and 7 were derived from 1H-NMR. studies. These were converted respectively into trans- and cis-5, 6-dihydro-4, 6-dimethyl-4 H, 8 H-pyrido [3, 2, 1-de]phenanthridin-8-ones 18 and 20 by a Pschorr reaction on the anthranilamides 10 and 15. Bromophenanthridones 19 and 21 were similarly prepared from bromoanthranilamides 12 and 17. Detailed 1H-NMR. studies on 18 and 20 indicated axial disposition of the methyl groups at C(2) in both compounds in contrast to the situation in 6 and 7. This is presumably to avoid adverse CH3CO group interaction of the A (1, 3) type. The severity of this is gauged by the preference of 20 for a normally forbidding 1, 3-diaxial orientation of two methyl groups. X-ray crystallographic studies on 19 and 20 confirm the stereochemical assignments.
- Publication
Helvetica Chimica Acta, 1978, Vol 61, Issue 4, p1246
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19780610407