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Some novel cyclizations of propiophenones with chlorosulfonic acid
Author(s) -
Meyer Robert F.
Publication year - 1966
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.5570030213
Subject(s) - chemistry , pyrrolidine , nucleophile , ring (chemistry) , mannich reaction , medicinal chemistry , reaction conditions , organic chemistry , catalysis
The reaction of chlorosulfonie acid with propiophenones was found to give the 3‐chloro‐2‐methylbenzothiophene‐1, 1‐dioxides (I) and (VIII); reaction of Mannich bases of aceto‐phenone, with chlorosulfonie acid, gave the corresponding 3‐chloro‐2‐substituted amino‐methylbenzothiophene‐1,1‐dioxides (IX) and (X). The above structures were established by reaction with various nucleophiles and by hydrogenation. o ‐Hydroxypropiophenones, under the above conditions, are cyclized to the cyclic sulfones (XII) and (XIII). Ring opening with pyrrolidine gave the corresponding phenolic sulfonamides (XIV) and (XV).