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A (1,3) Strain in cis- and trans-5, 6-dihydro-4, 6-dimethyl-4H, 8H-pyrido [3,2,1-de]phenanthridin-8-ones

✍ Scribed by Kuppuswamy Nagarajan; Rashmi K. Shah; Hermann Fuhrer; Reginal T. Puckett; Mathur R. Narasimhamurthy; Kailasam Venkatesan

Publisher
John Wiley and Sons
Year
1978
Tongue
German
Weight
611 KB
Volume
61
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The stereochemistry of trans‐ and cis‐2, 4‐dimethyl‐tetrahydroquinolines, 6 and 7 were derived from ^1^H‐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 ^1^H‐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 CH~3~CO 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.

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