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Preparation of potentially bioactive aza and thiaza polycyclic compounds containing a bridgehead nitrogen atom. Synthesis of pyrrolo[1,2,3‐ de ]‐1,4‐benzothiazine derivatives
Author(s) -
Armenise Domenico,
Trapani Giuseppe,
Arrivo Vittorio,
Morlacchi Flaviano
Publication year - 1990
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.5570270601
Subject(s) - benzothiazine , chemistry , nitrogen atom , alkylation , yield (engineering) , nitrogen , medicinal chemistry , stereochemistry , organic chemistry , combinatorial chemistry , ring (chemistry) , catalysis , materials science , metallurgy
The synthesis of some pyrrolo[1,2,3‐ de ]‐1,4‐benzothiazine derivatives by using a modified Bischler type cyclization of N ‐(2,2‐diethoxyethyl)‐2 H ‐1,4‐benzothiazines as a crucial step is described. The alternative approach based on Friedel‐Crafts alkylation of the N ‐(2‐chloroethyl)‐2 H ‐1,4‐benzothiazines is shown to be impractical due to the low yield obtained.