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Synthesis of 3‐Bromoindenes from 4‐Alkynyl Alcohols/Sulfonamides and Aldehydes via Prins Cyclization, Ring‐Opening and Friedel‐Crafts Reactions
Author(s) -
Kotipalli Trimurtulu,
Hou DuenRen
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900292
Subject(s) - chemistry , prins reaction , friedel–crafts reaction , ring (chemistry) , yield (engineering) , aryl , brønsted–lowry acid–base theory , aldehyde , organic chemistry , medicinal chemistry , catalysis , materials science , alkyl , metallurgy
A one‐pot, two‐staged protocol has been developed for the synthesis of 3‐bromoindenes from aryl alkynyl alcohols/sulfonamides and aldehydes. Bromotrimethylsilane (TMSBr) initiated a halo‐Prins cyclization reaction to give 3‐(bromomethylene)‐tetrahydropyrans or ‐piperidines, which underwent ring‐opening and Friedel‐Crafts allylation to yield 3‐bromoindenes in the presence of Brønsted acids.