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Synthesis of 2,3‐dihydrospiro[benzofuran‐2,4′ ‐piperidines] and 2,3‐dihydrospiro[benzofuran‐2,3′‐pyrrolidines]
Author(s) -
Effland Richard C.,
Gardner Beth Ann,
Strupczewski Joseph
Publication year - 1981
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.5570180438
Subject(s) - benzofuran , chemistry , piperidine , pyrrolidine , nitration , yield (engineering) , derivative (finance) , organic chemistry , ketone , intramolecular force , medicinal chemistry , materials science , economics , financial economics , metallurgy
The synthesis of 2,3‐dihydrospiro[benzofuran‐2,4′‐piperidines] 3 and 2,3‐dihydrospiro[benzofuran‐2,3′]‐pyrrolidine] 6 is described. The synthesis was achieved by a Grignard reaction of a 2‐fluorobenzylhalide with an appropriate cycloazaalkyl ketone to yield the tertiary alcohols 1 and 4 . Subsequent intramolecular displacement of the aromatic fluoride by the derived alkoxides provided the novel system. Nitration of 1′‐acetyl‐2,3‐dihydrospiro[benzofuran‐2,4′‐piperidine] 7 resulted in a 5‐nitro derivative.