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Reaction of 1‐benzoselenopyrylium salts with grignard reagents: Formation of 2,4‐disubstituted selenochromenes and their conversion into the corresponding 1‐benzoselenopyrylium salts
Author(s) -
Sashida Haruki,
Yoshida Masahiro,
Minamida Hiroshi,
Teranishi Masanori
Publication year - 2002
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.5570390226
Subject(s) - chemistry , halide , tetrafluoroborate , salt (chemistry) , reagent , magnesium , medicinal chemistry , alkyl , grignard reagent , nucleophile , nucleophilic addition , grignard reaction , organic chemistry , ionic liquid , catalysis
Treatment of 2‐ tert ‐butyl‐1‐benzoselenopyrylium salts 1A and 2‐phenyl‐1‐benzoselenopyrylium salts 1B with an alkyl(phenyl)magnesium halide resulted in nucleophilic addition at the C‐4 position to give the corresponding 2,4‐disubstituted 4 H ‐selenochromenes 2A and 2B in good yields, respectively. The obtained selenochromenes 2 were then easily converted into the 4‐substituted 2‐ tert ‐butyl‐1‐benzoselenopyrylium salts 6A by treatment with triphenylcarbenium tetrafluoroborate in high yields. The 4‐substituted 2‐phenyl derivatives 6B were also obtained in a similar manner. The reaction of the unsubstituted 1‐benzoselenopy‐rylium salt 1C with an alkylmagnesium halide is also described.