Unexpected Formation of Benzothiazoles in the Synthesis of New Heterocycles: Benzo-1,2,4-dithiazines

FAJKUSOVÁ, Dagmar and Pavel PAZDERA. Unexpected Formation of Benzothiazoles in the Synthesis of New Heterocycles: Benzo-1,2,4-dithiazines. Synthesis. Stuttgart - New York: Georg Thieme Verlag, 2008, vol. 2008, No 8, p. 1297-1305. ISSN 0039-7881.

Basic information

• Original name: Unexpected Formation of Benzothiazoles in the Synthesis of New Heterocycles: Benzo-1,2,4-dithiazines
• Name in Czech: Unexpected Formation of Benzothiazoles in the Synthesis of New Heterocycles: Benzo-1,2,4-dithiazines
• Authors: FAJKUSOVÁ, Dagmar (203 Czech Republic) and Pavel PAZDERA (203 Czech Republic, guarantor).
• Edition: Synthesis, Stuttgart - New York, Georg Thieme Verlag, 2008, 0039-7881.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10401 Organic chemistry
• Country of publisher: Germany
• Confidentiality degree: is not subject to a state or trade secret
• Impact factor: Impact factor: 2.470
• RIV identification code: RIV/00216224:14310/08:00024702
• Organization unit: Faculty of Science
• UT WoS: 000255365400019
• Keywords in English: benzodithiazines; benzothiazoles; cyclizations; heterocycles; sulfur
• Tags: benzodithiazines, benzothiazoles, Cyclizations, heterocycles, Sulfur
• Tags: International impact, Reviewed

Abstract

The synthesis of benzo-1,2,4-dithiazines was investigated presuming a reversible sulfur-sulfur bond formation. 2-Aminothiophenol, when allowed to react with isothiocyanates, provided benzothiazoles. 2,2'-Diaminodiphenyl disulfide underwent cyclizations very readily without any reducing agent to give, according to the reaction conditions, benzothiazoles or benzo-1,2,4-dithiazines. The developed proceduře offers a simple and convenient way to prepare the title compounds in very good to excellent yields. Until now, benzo-1,2,4-dithiazines as well as 2,2'-diaminodiphenyl disulfides bearing aminocarbonothioyl groups were unknown.

Abstract (in Czech)

The synthesis of benzo-1,2,4-dithiazines was investigated presuming a reversible sulfur-sulfur bond formation. 2-Aminothiophenol, when allowed to react with isothiocyanates, provided benzothiazoles. 2,2'-Diaminodiphenyl disulfide underwent cyclizations very readily without any reducing agent to give, according to the reaction conditions, benzothiazoles or benzo-1,2,4-dithiazines. The developed proceduře offers a simple and convenient way to prepare the title compounds in very good to excellent yields. Until now, benzo-1,2,4-dithiazines as well as 2,2'-diaminodiphenyl disulfides bearing aminocarbonothioyl groups were unknown.

Links

• GA203/01/1333, research and development project: Name: Chalkogenorganické sloučeniny - příprava, transformace a strukturní studie

Investor: Czech Science Foundation, Chalcogen organic compounds - synthesis, transformation and structure elucidation

• MSM 143100011, plan (intention): Name: Struktura a vazebné poměry, vlastnosti a analýza syntetických a přírodních molekulových ansamblů

Investor: Ministry of Education, Youth and Sports of the CR, Structure and character of bonding, properties and analysis of synthetic and natural molecular ensembles

• 2A-1TP1/090, research and development project: Name: Nové katalyzátory a činidla pro udržitelné zelené syntézy a kombinatoriální syntézy.

Investor: Ministry of Industry and Trade of the CR, New catalysts and reagents for sustainable green syntheses and combinatorial syntheses