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The Rearrangment of 3‐Aminobenzo‐[ b ]thiophenes to Tricyclic Benzoisothiazoles as Result of a Simple Azo‐coupling Procedure
Author(s) -
Klimas Susann,
Beckert Rainer,
Hartmann Horst,
Görls Helmar
Publication year - 2016
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.2475
Subject(s) - chemistry , cinnoline , tricyclic , sulfanyl , benzothiophene , derivative (finance) , carboxylate , medicinal chemistry , salt (chemistry) , stereochemistry , computational chemistry , organic chemistry , thiophene , economics , financial economics
As a result of the reaction of ethyl 3‐amino‐4‐dimethylamino‐benzothiophene‐2‐carboxylate ( 1 ) with 2‐thiazolediazonium salt 2 , tricyclic ethyl 5‐(thiazol‐2‐yl)‐8‐(thiazol‐2‐yldiazenyl)‐5H‐isothiazolo[3,4,5‐d,e]cinnoline‐3‐carboxylate 4 , instead of the expected 7‐thiazolylazo derivative 3 , is formed. A mechanism in which sulfanyl cations occur as intermediates is proposed.