The Rearrangment of 3‐Aminobenzo‐[ b ]thiophenes to Tricyclic Benzoisothiazoles as Result of a Simple Azo‐coupling Procedure | Zendy

Klimas Susann | Zendy; Beckert Rainer | Zendy; Hartmann Horst | Zendy; Görls Helmar | Zendy

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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.

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