Synthesis of an indole analog of magallanesine  via  the [1,2]‐meisenheimer rearrangement | Zendy

Yoneda Ryuji | Zendy; Kimura Tetsuya | Zendy; Kinomoto Junko | Zendy; Harusawa Shinya | Zendy; Kurihara Takushi | Zendy

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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 .

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