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Synthesis of an indole analog of magallanesine via the [1,2]‐meisenheimer rearrangement
Author(s) -
Yoneda Ryuji,
Kimura Tetsuya,
Kinomoto Junko,
Harusawa Shinya,
Kurihara Takushi
Publication year - 1996
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.5570330658
Subject(s) - chemistry , indole test , intramolecular force , ring (chemistry) , heck reaction , medicinal chemistry , stereochemistry , organic chemistry , catalysis , palladium
Ring expansion of azetopyridoindole 11 via the [1,2]‐Meisenheimer rearrangement of the corresponding N ‐oxide 12 gave azocinoindole 14 , which was converted into the N ‐benzoylenaminone 18 in 5 steps. Intramolecular cyclization of 18 was accomplished by a modified Heck reaction followed by reductive desulfonylation to provide the indole analog 2, 5 H ‐isoindolo[2′,1′;1,2]azocino[5,6‐ b ]indole, of magallanesine 1 .