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Intramolekulare Diels‐Alder ‐Additionen von 1,2‐Dihydropyridinen
Author(s) -
Greuter Hans,
Schmid Hans
Publication year - 1974
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19740570432
Subject(s) - chemistry , intramolecular force , pyridinium , sodium borohydride , diels–alder reaction , medicinal chemistry , sodium hydroxide , tricyclic , organic chemistry , catalysis
Reduction of the pyridinium salts 1b‐f in methanolic sodium hydroxide solution with sodium borohydride gave the dimeric dihydropyridine derivatives 3b‐f . Heating these dimers in hydrocarbon solvents at 110–207° resulted in the formation of the tricyclic amines 4c–f , which were shown to be products of an intramolecular Diels‐Alder addition within the intermediate dihydropyridines 2c–f . The structures of 4c–f were deduced from spectroscopic, mainly NMR. data.