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

authored by

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.

Organisation(s)

Institute of Organic Chemistry

External Organisation(s)

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

Type

Article

Journal

MOLECULES

Volume

12

Pages

2017-2028

No. of pages

12

ISSN

1420-3049

Publication date

08.2007

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

Analytical Chemistry, Chemistry (miscellaneous), Molecular Medicine, Pharmaceutical Science, Drug Discovery, Physical and Theoretical Chemistry, Organic Chemistry

Sustainable Development Goals

SDG 3 - Good Health and Well-being

Electronic version(s)

https://doi.org/10.3390/12082017 (Access: Open)