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Azepines by photochemical ring enlargement of 9‐azidopodophyllotoxin‐ and 9‐azido‐9′ ‐demethylepipodophyllotoxin derivatives
Author(s) -
Laatsch Hartmut,
Erns Bernd Peter,
Hoffmann Dieter
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199510248
Subject(s) - chemistry , aziridine , podophyllotoxin , nitrene , ring (chemistry) , cyclohexene , photochemistry , stereochemistry , organic chemistry , catalysis
The azepines 5a‐5c were obtained by photochemical nitrene rearrangement of the azides 1e/1f and 4b/4c in cyclohexene, but not in other solvents. They are ring expansion products of podophyllotoxin ( 1a ) and resemble steganacin ( 9 ), but show only low biological activity. The triazenes 7a/8a and the aziridine 8b are also less active than 1a .