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Compounds with bridgehead nitrogen 66—NMR spectra and stereochemistry of derivatives of 1,2,3,4,6,7,12,12b- octahydropyrimido [1′, 6′:1,2] pyrido [3,4-b]indol-2-one and of 1,3,4,6,7,11b-hexahydropyrimido [6,1-a] isoquinolin-2-one

✍ Scribed by Trevor A. Crabb; Asmita V. Patel

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
268 KB
Volume
29
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Comparison of the NMR spectra of 3‐methyl‐1,2,3,4,6,7,12,12b‐octahydropyrimido [1′,6′ : 1,2]pyrido[3,4‐b] indol‐2‐one and of cis‐(H‐6, H‐12b)‐3,6‐dimethyl‐ 1,2,3,4,6,7,12,12b‐octahydropyrimido [1′,6′:1,2]pyrido[3,4‐b] indol‐2‐one shows the former to exist in solution at 25°C as an equilibrium mixture containing ca. 20% N‐inside‐cis‐ and ca. 80% trans‐fused conformers, and the latter to adopt exclusively the trans‐fused conformer. The related 3‐methyl‐ 1,3,4,6,7,11b‐ hexahydropyrimido [6,1‐a] isoquinoline‐2‐one adopts a ca. 53% trans‐fused 47% cis‐fused equilibrium.

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