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Novel solid‐state synthesis of dimeric 4‐aryl‐1,4‐dihydropyridines
Author(s) -
Hilgeroth Andreas,
Heinemann Frank W.
Publication year - 1998
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570350217
Subject(s) - chemistry , dimer , cycloaddition , aryl , pyridine , solid state , photochemistry , stereochemistry , medicinal chemistry , crystallography , organic chemistry , catalysis , alkyl
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 .
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