Premium
The reaction of arylmagnesium bromides with N ‐(ω‐bromoalkyl)phthalimides
Author(s) -
Braun Loren L.,
Xia Jing,
Cooney Mark J.,
Ahmed Mohammed K.,
Isaacson Eugene I.
Publication year - 1989
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.5570260538
Subject(s) - phenylmagnesium bromide , chemistry , phthalimides , reagent , organic chemistry , tetrahydrofuran , bromide , alcohol , grignard reaction , grignard reagent , ether , medicinal chemistry , phthalimide , solvent
The reaction of the N ‐(ω‐bromoalkyl)phthalimides, 1 and 2, with a series of arylmagnesium bromides in tetrahydrofuran yielded the corresponding oxazoloisoindoles 4a‐4h and oxazinoisoindoles 5a‐5f. At low temperatures, phenylmagnesium bromide, on treatment with 1 and 2 , yielded the open‐chain alcohols, 7 and 8. With 3, phenylmagnesium bromide yielded the corresponding alcohol 9 under any conditions utilized. In several cases, the products isolated from the reaction of 1 with arylmagnesium bromides were shown to depend on the order of addition, with monoarylated oxazoloisoindoles 4c and 4d being formed when the Grignard reagent was added to 1 , and triarylated products 10a and 10b formed when the order of addition was reversed. A further triarylated product 10c was also obtained by the latter method.