An improved synthesis of 4-chlorocoumarin-3-sulfonyl chloride and its reactions with different bidentate nucleophiles to give pyrido[1′, 2′:2,3]- and thiazino[3′,2′:2,3]-1,2,4-thiadiazino[6,5-c] benzopyran-6-one 7,7-dioxides

verfasst von

Ahmed Jashari, Evamarie Hey-Hawkins, Bozhana Mikhova, Gerald Draeger, Emil Popovski

Abstract

An improved synthetic method affording 4-chlorocoumarin-3-sulfonyl chloride (4) in very good yield (ca. 85 %) is reported. This compound was reacted with various bidentate nucleophiles such as 2-aminopyridines and 2-aminothiazoles in order to obtain substituted pyrido- and thiazino-1,2,4-thiadiazino-benzopyranone dioxides (potential anticancer and anti-HIV agents). These reactions occurred rapidly at room temperature giving yellowish precipitates, which are insoluble in common organic solvents, making the purification process challenging. Further investigation has shown that these fused heterocycles are not stable and decompose with opening of the 1,2,4-thiadiazine ring.

Organisationseinheit(en)

Institut für Organische Chemie

Externe Organisation(en)

Ss. Cyril and Methodius University
Universität Leipzig
Bulgarian Academy of Sciences (BAS)

Typ

Artikel

Journal

MOLECULES

Band

12

Seiten

2017-2028

Anzahl der Seiten

12

ISSN

1420-3049

Publikationsdatum

08.2007

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Analytische Chemie, Chemie (sonstige), Molekularmedizin, Pharmazeutische Wissenschaften, Wirkstoffforschung, Physikalische und Theoretische Chemie, Organische Chemie

Ziele für nachhaltige Entwicklung

SDG 3 – Gute Gesundheit und Wohlergehen

Elektronische Version(en)

https://doi.org/10.3390/12082017 (Zugang: Offen)