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Novel solid-state synthesis of dimeric 4-aryl-1,4-dihydropyridines

✍ Scribed by Andreas Hilgeroth; Frank W. Heinemann


Book ID
102339346
Publisher
Journal of Heterocyclic Chemistry
Year
1998
Tongue
English
Weight
466 KB
Volume
35
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

On irradiation in the solid state the 4‐aryl‐1,4‐dihydroypridines 1 undergo [2+2] cycloadditon to centrosymmetric head‐to‐tail dimers 3 and 4a. The almost exclusive formation of the cage dimers 3 via the C~2~‐symmetric syn‐dimers 2 takes place in nearly quantitative yields, in contrast with the cycloaddition reaction of the anti‐dimer 4a, which is accompanied by photooxidation to pyridine 5a.


πŸ“œ SIMILAR VOLUMES


ChemInform Abstract: Novel Solid-State S
✍ A. HILGEROTH; F. W. HEINEMANN πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 31 KB πŸ‘ 1 views

Novel Solid-State Synthesis of Dimeric 4-Aryl-1,4-dihydropyridines. -On irradiation in the solid state, 4-aryldihydropyridines (I) and (IV) undergo [2 + 2] cycloaddition to centrosymmetric head-to-tail dimers (II) and (V), respectively. Further irradiation of the dimers (II) provides the cage dimers

Solution-Dimerization of 4-Aryl-1,4-dihy
✍ Andreas Hilgeroth; Ute Baumeister; Frank W. Heinemann πŸ“‚ Article πŸ“… 2000 πŸ› John Wiley and Sons 🌐 English βš– 320 KB πŸ‘ 1 views

On irradiation at Ξ» Υ† 270 nm solutions of 4-aryl-1,4-Irradiation with filtered light (Ξ» ΟΎ 313 nm) leads to syn and anti dimers 4 and 3 in nearly equal yields. The poor yields of dihydropyridines 1 yield cage dimers 2 as the main products beside small amounts of anti dimers 3. 1 H-NMR data and X-anti