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Synthesis of 3‐benzoyl‐3,4‐dihydro‐2 H ‐ and 3,4‐dihydro‐2,2‐disubstituted‐benzopyrans via alkynyl grignard reagents
Author(s) -
Adegoke Emmanuel A.,
Emokpae T. A.,
EphraimBassey H.,
Oyelola C. A.
Publication year - 1987
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.5570240640
Subject(s) - chemistry , phenylacetylene , aldehyde , ketone , benzopyrans , allene , magnesium bromide , reagent , bromide , organic chemistry , magnesium , medicinal chemistry , catalysis
The versatility of the new route to a substituted chromane via a lithiated allene recently described by us [1] is reported. The relatively more stable alkynols 2–4 were readily identified and thus provide evidence for the formation of vinyl acetylene carbinol as an intermediate in the new route. Accordingly, phenylacetylene magnesium bromide [2] reacted with suitable aldehyde or ketone to give the alkynols 2–4 which condensed further with the same or different aldehyde or ketone to give 3‐benzoyl heteroring‐substituted chromanes 5–17.