Synthesis of bis[1,2]dithiolo[1,4]thiazine imines from Hünig's base

Amelichev, Stanislav A.; Barriga, Susana; Konstantinova, Lidia S.; Markova, Tatjana B.; Ракитин, Олег А.; Rees, Charles W.; Torroba, Tomás

doi:10.1039/b105243h

Cited by 18 publications

(7 citation statements)

References 9 publications

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“…The complete sulfuration of the Hünig's base, affordable by extensive reaction with S 2 Cl 2 and DABCO, gave rise to a expected intermediate disalt E, from which a complete range of di [1,2]dithiolo [1,4]thiazine derivatives could be obtained by trapping of the intermediate salts with sulfur and oxygen nucleophiles, [19,20] as well as nitrogen nucleophiles, [21] giving rise to several dithiole derivatives 46-50 (Scheme 13). Scheme 13. The sulfur atom of the 1,4-thiazine ring was easily extruded in all the N-substituted di [1,2]dithiolo- [1,4]thiazine derivatives (but not in the N-unsubstituted) yielding pyrrole derivatives 51-53 (Scheme 14).…”

Section: 2-dithioles From Isopropylaminesmentioning

confidence: 99%

Heterocyclic Chemistry of Sulfur Chlorides – Fast Ways to Complex Heterocycles

Garcı́a-Valverde

Torroba

2006

Eur J Org Chem

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This microreview highlights the most important advances in the synthetic applications of sulfur dichloride and disulfur dichloride for the preparation of heterocycles. Sulfur chlorides can be considered some of the best sulfur‐transfer reagents for the synthesis of heterocyclic systems. Their high reactivity towards nucleophilic organic compounds such as alkenes, alkynes, amines, nitriles, oximes, and their both chlorinating and sulfurating character explain the extensive use of these reagents. In many cases, the initial reactions give rise to reactive intermediates that can be trapped by nucleophiles in a tandem fashion, expanding the possibilities of the reactions. In this way, several new heterocyclic systems can be obtained by a careful selection of the appropriate combination of reagents. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Section: 2-dithioles From Isopropylaminesmentioning

confidence: 99%

Heterocyclic Chemistry of Sulfur Chlorides – Fast Ways to Complex Heterocycles

Garcı́a-Valverde

Torroba

2006

Eur J Org Chem

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“…Konstantinova and coworkers synthesized the bis(1,2)dithiolo derivative of 1,4-thiazine class (Scheme 16) by treating 4-isopropylamino-5-chloro-1,2-dithiole-3-ones with sulfuryl chloride in acetonitrile as a solvent that resulted in the formation of an intermediate salt of bis(1,2)dithiolo(1,4)thiazine chloride [31,32]. When this intermediate salt is further treated with triethylamine (Scheme 16), it resulted in the desired product [31].…”

Section: Green Syntheses Of Thiazines and Their Derivativesmentioning

confidence: 99%

Bioactive Thiazine and Benzothiazine Derivatives: Green Synthesis Methods and Their Medicinal Importance

Badshah

Akhtar

2016

Molecules

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Abstract:Thiazines are a group of heterocyclic organic compounds that are still largely unexplored for their pharmacological activities. There are different available methods for the synthesis of thiazine derivatives in the literature. In this review, we discuss available methods of thiazine preparation through green synthesis methods. Beside their synthesis, many thiazine derivatives are biologically active and play an important role in the treatment of various diseases and show promising results of varying degrees, where they act as antibacterial, antifungal, antitumor, antimalarial, antineoplastic, antiviral, anti-inflammatory, analgesic and anticancer agents and thus they represent an interesting class of heterocyclic medicinal compounds worthy of further exploration.

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“…Dichlorodithiolium salt 123, obtained from diisopropylethylamine, S 2 Cl 2 and DABCO in chloroform at room temperature, reacts with arylsulfamides and their N,N H -dichloro derivatives to form diimines Ð bis(arylsulfonylimino)bis(dithiolo)thiazines 127 Ð in moderate yield (Scheme 63) 91. …”

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confidence: 99%