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

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

doi:10.3390/12082017

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

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

^*Corresponding author for this work

Institute of Organic Chemistry

Research output: Contribution to journal › Article › Research › peer review

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.

Original language	English
Pages (from-to)	2017-2028
Number of pages	12
Journal	MOLECULES
Volume	12
Issue number	8
DOIs	https://doi.org/10.3390/12082017
Publication status	Published - Aug 2007

UN Sustainable Development Goals (SDGs)

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

1,2,4-thiadiazines
Coumarin
Fused heterocycles
Synthesis

ASJC Scopus subject areas

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

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10.3390/12082017

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Jashari, A., Hey-Hawkins, E., Mikhova, B., Draeger, G., & Popovski, E. (2007). 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. MOLECULES, 12(8), 2017-2028. https://doi.org/10.3390/12082017

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title = "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",

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",

author = "Ahmed Jashari and Evamarie Hey-Hawkins and Bozhana Mikhova and Gerald Draeger and Emil Popovski",

year = "2007",

month = aug,

doi = "10.3390/12082017",

language = "English",

volume = "12",

pages = "2017--2028",

journal = "MOLECULES",

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Jashari, A, Hey-Hawkins, E, Mikhova, B, Draeger, G & Popovski, E 2007, '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', MOLECULES, vol. 12, no. 8, pp. 2017-2028. https://doi.org/10.3390/12082017

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. / Jashari, Ahmed; Hey-Hawkins, Evamarie; Mikhova, Bozhana et al.
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

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

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U2 - 10.3390/12082017

DO - 10.3390/12082017

M3 - Article

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AN - SCOPUS:34548402110

SN - 1420-3049

VL - 12

SP - 2017

EP - 2028

JO - MOLECULES

JF - MOLECULES

IS - 8

ER -

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

Abstract

UN Sustainable Development Goals (SDGs)

Keywords

ASJC Scopus subject areas

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