Details
| Original language | English |
|---|---|
| Pages (from-to) | 2017-2028 |
| Number of pages | 12 |
| Journal | MOLECULES |
| Volume | 12 |
| Issue number | 8 |
| Publication status | Published - Aug 2007 |
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.
Keywords
- 1,2,4-thiadiazines, Coumarin, Fused heterocycles, Synthesis
ASJC Scopus subject areas
- Chemistry(all)
- Analytical Chemistry
- Chemistry(all)
- Chemistry (miscellaneous)
- Biochemistry, Genetics and Molecular Biology(all)
- Molecular Medicine
- Pharmacology, Toxicology and Pharmaceutics(all)
- Pharmaceutical Science
- Pharmacology, Toxicology and Pharmaceutics(all)
- Drug Discovery
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
Sustainable Development Goals
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In: MOLECULES, Vol. 12, No. 8, 08.2007, p. 2017-2028.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - 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
AU - Jashari, Ahmed
AU - Hey-Hawkins, Evamarie
AU - Mikhova, Bozhana
AU - Draeger, Gerald
AU - Popovski, Emil
N1 - Copyright: Copyright 2009 Elsevier B.V., All rights reserved.
PY - 2007/8
Y1 - 2007/8
N2 - 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.
AB - 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.
KW - 1,2,4-thiadiazines
KW - Coumarin
KW - Fused heterocycles
KW - Synthesis
UR - http://www.scopus.com/inward/record.url?scp=34548402110&partnerID=8YFLogxK
U2 - 10.3390/12082017
DO - 10.3390/12082017
M3 - Article
C2 - 17960102
AN - SCOPUS:34548402110
VL - 12
SP - 2017
EP - 2028
JO - MOLECULES
JF - MOLECULES
SN - 1420-3049
IS - 8
ER -