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
Novel solid-state synthesis of dimeric 4-aryl-1,4-dihydropyridines
β 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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β¦ Synopsis
Abstract
On irradiation in the solid state the 4βarylβ1,4βdihydroypridines 1 undergo [2+2] cycloadditon to centrosymmetric headβtoβtail dimers 3 and 4a. The almost exclusive formation of the cage dimers 3 via the C~2~βsymmetric synβdimers 2 takes place in nearly quantitative yields, in contrast with the cycloaddition reaction of the antiβdimer 4a, which is accompanied by photooxidation to pyridine 5a.
π SIMILAR VOLUMES
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