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Research on potentially bioactive aza and thiaza polycyclic compounds containing a bridgehead nitrogen atom. III . Synthesis and antimicrobial activity of some 1,4‐benzothiazines and pyrrolobenzothiazines
Author(s) -
Armenise Domenico,
Trapani Giuseppe,
Arrivo Vittorio,
Laraspata Elena,
Morlacchi Flaviano
Publication year - 2000
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.5570370634
Subject(s) - chemistry , benzothiazine , antimicrobial , nitrogen atom , chloroform , sulfide , nitrogen , organic chemistry , medicinal chemistry , combinatorial chemistry , group (periodic table)
Cyclization reactions of N ‐(2,2‐dialkoxyethyl)‐1,4‐benzothiazine lactams 2 and 1,4‐benzothiazine‐sulfones 10 lead to the corresponding pyrrolo[1,2,3‐ de ]‐1,4‐benzothiazines 4 and 12, respectively, by using the dioxane/ p ‐toluenesulfonic acid or polyphosphoric acid/chloroform systems. In contrast, in the same reaction conditions, 1,4‐benzothiazines 5a‐h do not provide the expected pyrrolobenzothiazines 7, and as for 5c‐h considerable amount of the 2‐amino‐phenyl‐sulfide 8 was obtained. The results of microbiological assays are reported.