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Synthesis of 1,4‐Dihydropyridine Nucleosides by Photochemical Cycloaddition
Author(s) -
Tietze Lutz F.,
Bergmann Andreas
Publication year - 1985
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198501271
Subject(s) - dihydropyridine , cycloaddition , chemistry , glycosyl , alkene , toluene , yield (engineering) , ring (chemistry) , photochemistry , medicinal chemistry , organic chemistry , calcium , materials science , catalysis , metallurgy
The 1,4‐dihydropyridine nucleosides 4 are formed in almost quantitative yield when 2‐hydroxytetrahydropyridines 3 are heated in toluene in the presence of a (4 Å) molecular sieve. The tetrahydropyridines 3 are likewise formed almost quantitatively on irradiation of a mixture of a N ‐glycosyl enaminecarbaldehyde 1 and an alkene 2 . The method enables wide variation of the substituents and labeling of the dihydropyridine ring (R 1 =sugar residue, R 2 , R 3 =H, CH 3 , CO 2 CH 3 , CO 2 t Bu).
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