Synthesis and structure of cycloalkane- and norbornane-condensed 6-aryl-1,2,4,5-tetrahydropyridazinones
✍ Scribed by Ferenc Csende; Anasztárzia Hetényi; Géza Stájer; Ferenc Fülöp
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2004
- Tongue
- English
- Weight
- 220 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
The C=N double bond of certain cis‐ or trans‐cycloalkane and diexo‐ or diendo‐norbornane‐condensed pyridazinones was reduced with NaBH~3~CN. The cis‐ or trans nature of the starting cycloalkane derivatives was always retained in the saturated products, with a high degree of diastereoselectivity: the hydrogen on the new stereocenter and the annelational hydrogen next to the carbonyl always exhibited the same steric orientation. The stereostructures were determined by means of nmr measurements and confirmed by molecular modelling.
📜 SIMILAR VOLUMES
## Abstract A general method is described for the synthesis of 1‐aryl‐2‐alkyl‐1,4,5,6‐tetrahydropyrimidines 1, by cyclization of __N__‐acyl‐__N__′‐aryltrimethylenediamines 2 with trimethylsilyl polyphosphate. Precursors 2 were obtained by aminolysis of the corresponding __N__‐(3‐bromopropyl)amides