e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

Extrusion reactions-VII

H Singh, SK Aggarwal, N Malhotra

Index: Singh, Harjit; Aggarwal, Sunil K.; Malhotra, Nageshwar Tetrahedron, 1984 , vol. 40, # 23 p. 4941 - 4946

Full Text: HTML

Citation Number: 0

Abstract

ω-(2, 6-Dimethyl-4-pyrimidinylthio-(4), 2-methyl-4-quinazolinylthio-(9), and 4-oxo-2-quinazo- linylthio)-(10) acetophenones with hydrochloric or perchloric acid provide 2, 5-diaryl-1, 4- dithiins (7) whereas α)-(6-methyl-4-pyrimidinylthio) acetophenones (11) with aq HCl/HClO4, or POCl3 followed by hydrolysis provide 1-(4-aryl-2-thiazolyl)-2-propanones (12). Likewise, 2-(6-methyl-4-pyrimidinylthio) cyclohexanone (13) give the thiazole derivative (14).

4'-chloro-ω-(4-(2,6-dimethylpyrimidinyl)thio)-acetophenone Structure

4'-chloro-ω-(4-...

~53%

2,6-Dimethyl-4(1H)-pyrimidinone Structure

2,6-Dimethyl-4(...

2,5-Di(4-chlorophenyl)-1,4-dithiin Structure

2,5-Di(4-chloro...

Benzoyleneurea Structure

2-[2-(4-chloro-phenyl)-2-oxo-ethylsulfanyl]-3H-quinazolin-4-one Structure

2-[2-(4-chloro-...

~58%

2,5-Di(4-chlorophenyl)-1,4-dithiin Structure

2,5-Di(4-chloro...

Benzoyleneurea Structure

1-(4-chlorophenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-chlorophen...

~15%

4-Hydroxy-6-methylpyrimidine Structure

4-Hydroxy-6-met...

2,5-Di(4-chlorophenyl)-1,4-dithiin Structure

2,5-Di(4-chloro...

1-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]propan-2-one Structure

1-[4-(4-chlorop...

2-Bromo-4'-chloroacetophenone Structure

2-Bromo-4'-chlo...

~%

2,5-Di(4-chlorophenyl)-1,4-dithiin Structure

2,5-Di(4-chloro...

1-(4-chlorophenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-chlorophen...

~10%

2,5-Di(4-chlorophenyl)-1,4-dithiin Structure

2,5-Di(4-chloro...

1-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]propan-2-one Structure

1-[4-(4-chlorop...

4(1H)-Pyrimidinethione, 6-methyl- (9CI) Structure

4(1H)-Pyrimidin...

2-Bromoacetophenone Structure

2-Bromoacetophenone

~77%

2-(6-methylpyrimidin-4-yl)sulfanyl-1-phenylethanone Structure

2-(6-methylpyri...

4-Hydroxy-6-methylpyrimidine Structure

4-Hydroxy-6-met...

~%

2-(6-methylpyrimidin-4-yl)sulfanyl-1-phenylethanone Structure

2-(6-methylpyri...

PTP inhibitor 1 Structure

PTP inhibitor 1

~%

2,5-Bis(4-methoxyphenyl)-1,4-dithiin Structure

2,5-Bis(4-metho...

4'-methoxy-ω-(4-(2,6-dimethylpyrimidinyl)thio)-acetophenone Structure

4'-methoxy-ω-(4...

~45%

2,6-Dimethyl-4(1H)-pyrimidinone Structure

2,6-Dimethyl-4(...

2,5-Bis(4-methoxyphenyl)-1,4-dithiin Structure

2,5-Bis(4-metho...

Benzoyleneurea Structure

2-(p-methoxyphenacylthio)quinazolin-4(3H)-one Structure

2-(p-methoxyphe...

~61%

2,5-Bis(4-methoxyphenyl)-1,4-dithiin Structure

2,5-Bis(4-metho...

Benzoyleneurea Structure

1-(4-methoxyphenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-methoxyphe...

~19%

4-Hydroxy-6-methylpyrimidine Structure

4-Hydroxy-6-met...

2,5-Bis(4-methoxyphenyl)-1,4-dithiin Structure

2,5-Bis(4-metho...

1-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]propan-2-one Structure

1-[4-(4-methoxy...

1-(4-methoxyphenyl)-2-((2-methylquinazolin-4-yl)thio)ethan-1-one Structure

1-(4-methoxyphe...

~51%

2-Methylquinazolin-4-ol Structure

2-Methylquinazo...

2,5-Bis(4-methoxyphenyl)-1,4-dithiin Structure

2,5-Bis(4-metho...

4(3H)-Quinazolinethione,2-methyl- Structure

4(3H)-Quinazoli...

~%

2,5-Bis(4-methoxyphenyl)-1,4-dithiin Structure

2,5-Bis(4-metho...

1-(4-methoxyphenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-methoxyphe...

~5%

2,5-Bis(4-methoxyphenyl)-1,4-dithiin Structure

2,5-Bis(4-metho...

1-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]propan-2-one Structure

1-[4-(4-methoxy...

4(1H)-Pyrimidinethione, 2,6-dimethyl- (9CI) Structure

4(1H)-Pyrimidin...

2,4′-dibromoacetophenone Structure

2,4′-dibromoace...

~70%

1-(4-bromophenyl)-2-(2,6-dimethylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-bromopheny...

4(1H)-Pyrimidinethione, 6-methyl- (9CI) Structure

4(1H)-Pyrimidin...

UNII:1134E5H2KV Structure

UNII:1134E5H2KV

~51%

2-(6-methylpyrimidin-4-yl)sulfanylcyclohexan-1-one Structure

2-(6-methylpyri...

4-Hydroxy-6-methylpyrimidine Structure

4-Hydroxy-6-met...

~%

2-(6-methylpyrimidin-4-yl)sulfanylcyclohexan-1-one Structure

2-(6-methylpyri...

1-(4-chlorophenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-chlorophen...

~40%

4-Hydroxy-6-methylpyrimidine Structure

4-Hydroxy-6-met...

2,5-Di(4-chlorophenyl)-1,4-dithiin Structure

2,5-Di(4-chloro...

1-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]propan-2-one Structure

1-[4-(4-chlorop...

1-(4-chlorophenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-chlorophen...

~48%

2,5-Di(4-chlorophenyl)-1,4-dithiin Structure

2,5-Di(4-chloro...

1-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]propan-2-one Structure

1-[4-(4-chlorop...

1-(4-bromophenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-bromopheny...

~38%

4-Hydroxy-6-methylpyrimidine Structure

4-Hydroxy-6-met...

2,5-Bis(4-bromophenyl)-1,4-dithiin Structure

2,5-Bis(4-bromo...

1-[4-(4-bromophenyl)-1,3-thiazol-2-yl]propan-2-one Structure

1-[4-(4-bromoph...

1-(4-bromophenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-bromopheny...

~50%

2,5-Bis(4-bromophenyl)-1,4-dithiin Structure

2,5-Bis(4-bromo...

1-[4-(4-bromophenyl)-1,3-thiazol-2-yl]propan-2-one Structure

1-[4-(4-bromoph...

1-(4-methylphenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-methylphen...

~34%

4-Hydroxy-6-methylpyrimidine Structure

4-Hydroxy-6-met...

2,5-Bis(4-methylphenyl)-1,4-dithiin Structure

2,5-Bis(4-methy...

1-[4-(4-methylphenyl)-1,3-thiazol-2-yl]propan-2-one Structure

1-[4-(4-methylp...

1-(4-methylphenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-methylphen...

~44%

2,5-Bis(4-methylphenyl)-1,4-dithiin Structure

2,5-Bis(4-methy...

1-[4-(4-methylphenyl)-1,3-thiazol-2-yl]propan-2-one Structure

1-[4-(4-methylp...

2-(2,6-dimethylpyrimidin-4-yl)sulfanyl-1-phenylethanone Structure

2-(2,6-dimethyl...

~50%

2,6-Dimethyl-4(1H)-pyrimidinone Structure

2,6-Dimethyl-4(...

p-Dithiin, 2,5-diphenyl- Structure

p-Dithiin, 2,5-...

2-(6-methylpyrimidin-4-yl)sulfanyl-1-phenylethanone Structure

2-(6-methylpyri...

~15%

4-Hydroxy-6-methylpyrimidine Structure

4-Hydroxy-6-met...

2-Propanone, 1-(4-phenyl-2-thiazolyl)- Structure

2-Propanone, 1-...

p-Dithiin, 2,5-diphenyl- Structure

p-Dithiin, 2,5-...

N/A Structure

~56%

2-Methylquinazolin-4-ol Structure

2-Methylquinazo...

p-Dithiin, 2,5-diphenyl- Structure

p-Dithiin, 2,5-...

2-Bromoacetophenone Structure

2-Bromoacetophenone

~%

p-Dithiin, 2,5-diphenyl- Structure

p-Dithiin, 2,5-...

4(3H)-Quinazolinethione,2-methyl- Structure

4(3H)-Quinazoli...

~%

p-Dithiin, 2,5-diphenyl- Structure

p-Dithiin, 2,5-...

2-(6-methylpyrimidin-4-yl)sulfanyl-1-phenylethanone Structure

2-(6-methylpyri...

~5%

2-Propanone, 1-(4-phenyl-2-thiazolyl)- Structure

2-Propanone, 1-...

p-Dithiin, 2,5-diphenyl- Structure

p-Dithiin, 2,5-...

4'-chloro-ω-(4-(2,6-dimethylpyrimidinyl)thio)-acetophenone Structure

4'-chloro-ω-(4-...

~0%

2,6-Dimethyl-4(1H)-pyrimidinone Structure

2,6-Dimethyl-4(...

2,5-Di(4-chlorophenyl)-1,4-dithiin Structure

2,5-Di(4-chloro...

Benzoyleneurea Structure

1-(4-bromophenyl)-2-(2,6-dimethylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-bromopheny...

~0%

2,6-Dimethyl-4(1H)-pyrimidinone Structure

2,6-Dimethyl-4(...

2,5-Bis(4-bromophenyl)-1,4-dithiin Structure

2,5-Bis(4-bromo...

Benzoyleneurea Structure

4'-methyl-ω-(4-(2,6-dimethylpyrimidinyl)thio)-acetophenone Structure

4'-methyl-ω-(4-...

~0%

2,6-Dimethyl-4(1H)-pyrimidinone Structure

2,6-Dimethyl-4(...

2,5-Bis(4-methylphenyl)-1,4-dithiin Structure

2,5-Bis(4-methy...

Benzoyleneurea Structure

4'-methoxy-ω-(4-(2,6-dimethylpyrimidinyl)thio)-acetophenone Structure

4'-methoxy-ω-(4...

~0%

2,6-Dimethyl-4(1H)-pyrimidinone Structure

2,6-Dimethyl-4(...

2,5-Bis(4-methoxyphenyl)-1,4-dithiin Structure

2,5-Bis(4-metho...

Benzoyleneurea Structure

2-[2-(4-bromo-phenyl)-2-oxo-ethylsulfanyl]-3H-quinazolin-4-one Structure

2-[2-(4-bromo-p...

~0%

2,5-Bis(4-bromophenyl)-1,4-dithiin Structure

2,5-Bis(4-bromo...

Benzoyleneurea Structure

2-[2-(4-chloro-phenyl)-2-oxo-ethylsulfanyl]-3H-quinazolin-4-one Structure

2-[2-(4-chloro-...

~0%

2,5-Di(4-chlorophenyl)-1,4-dithiin Structure

2,5-Di(4-chloro...

Benzoyleneurea Structure

2-(p-methoxyphenacylthio)quinazolin-4(3H)-one Structure

2-(p-methoxyphe...

~0%

2,5-Bis(4-methoxyphenyl)-1,4-dithiin Structure

2,5-Bis(4-metho...

Benzoyleneurea Structure

2-(2,6-dimethylpyrimidin-4-yl)sulfanyl-1-phenylethanone Structure

2-(2,6-dimethyl...

~0%

2,6-Dimethyl-4(1H)-pyrimidinone Structure

2,6-Dimethyl-4(...

p-Dithiin, 2,5-diphenyl- Structure

p-Dithiin, 2,5-...

4'-chloro-ω-(4-(2,6-dimethylpyrimidinyl)thio)-acetophenone Structure

4'-chloro-ω-(4-...

~0%

2,6-Dimethyl-4(1H)-pyrimidinone Structure

2,6-Dimethyl-4(...

2,5-Di(4-chlorophenyl)-1,4-dithiin Structure

2,5-Di(4-chloro...

Benzoyleneurea Structure

1-(4-bromophenyl)-2-(2,6-dimethylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-bromopheny...

~0%

2,6-Dimethyl-4(1H)-pyrimidinone Structure

2,6-Dimethyl-4(...

2,5-Bis(4-bromophenyl)-1,4-dithiin Structure

2,5-Bis(4-bromo...

Benzoyleneurea Structure

4'-methyl-ω-(4-(2,6-dimethylpyrimidinyl)thio)-acetophenone Structure

4'-methyl-ω-(4-...

~0%

2,6-Dimethyl-4(1H)-pyrimidinone Structure

2,6-Dimethyl-4(...

2,5-Bis(4-methylphenyl)-1,4-dithiin Structure

2,5-Bis(4-methy...

Benzoyleneurea Structure

4'-methoxy-ω-(4-(2,6-dimethylpyrimidinyl)thio)-acetophenone Structure

4'-methoxy-ω-(4...

~0%

2,6-Dimethyl-4(1H)-pyrimidinone Structure

2,6-Dimethyl-4(...

2,5-Bis(4-methoxyphenyl)-1,4-dithiin Structure

2,5-Bis(4-metho...

Benzoyleneurea Structure

4(1H)-Pyrimidinethione, 6-methyl- (9CI) Structure

4(1H)-Pyrimidin...

2-Bromo-4'-chloroacetophenone Structure

2-Bromo-4'-chlo...

~73%

1-(4-chlorophenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-chlorophen...

4-Hydroxy-6-methylpyrimidine Structure

4-Hydroxy-6-met...

~%

1-(4-chlorophenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-chlorophen...

4(1H)-Pyrimidinethione, 6-methyl- (9CI) Structure

4(1H)-Pyrimidin...

2,4′-dibromoacetophenone Structure

2,4′-dibromoace...

~72%

1-(4-bromophenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-bromopheny...

4-Hydroxy-6-methylpyrimidine Structure

4-Hydroxy-6-met...

~%

1-(4-bromophenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-bromopheny...

4-Hydroxy-6-methylpyrimidine Structure

4-Hydroxy-6-met...

~%

1-(4-methylphenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-methylphen...

N/A Structure

~0%

2-Methylquinazolin-4-ol Structure

2-Methylquinazo...

2,5-Bis(4-methylphenyl)-1,4-dithiin Structure

2,5-Bis(4-methy...

N/A Structure

~0%

2-Methylquinazolin-4-ol Structure

2-Methylquinazo...

p-Dithiin, 2,5-diphenyl- Structure

p-Dithiin, 2,5-...

1-(4-methoxyphenyl)-2-((2-methylquinazolin-4-yl)thio)ethan-1-one Structure

1-(4-methoxyphe...

~0%

2-Methylquinazolin-4-ol Structure

2-Methylquinazo...

2,5-Bis(4-methoxyphenyl)-1,4-dithiin Structure

2,5-Bis(4-metho...

4(1H)-Pyrimidinethione, 2,6-dimethyl- (9CI) Structure

4(1H)-Pyrimidin...

2-Bromoacetophenone Structure

2-Bromoacetophenone

~78%

2-(2,6-dimethylpyrimidin-4-yl)sulfanyl-1-phenylethanone Structure

2-(2,6-dimethyl...

4(1H)-Pyrimidinethione, 6-methyl- (9CI) Structure

4(1H)-Pyrimidin...

2-bromo-4'-methylacetophenone Structure

2-bromo-4'-meth...

~66%

1-(4-methylphenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-methylphen...

4(1H)-Pyrimidinethione, 6-methyl- (9CI) Structure

4(1H)-Pyrimidin...

PTP inhibitor 1 Structure

PTP inhibitor 1

~64%

1-(4-methoxyphenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-methoxyphe...

4-Hydroxy-6-methylpyrimidine Structure

4-Hydroxy-6-met...

~%

1-(4-methoxyphenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-methoxyphe...

1-(4-methoxyphenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-methoxyphe...

~35%

4-Hydroxy-6-methylpyrimidine Structure

4-Hydroxy-6-met...

2,5-Bis(4-methoxyphenyl)-1,4-dithiin Structure

2,5-Bis(4-metho...

1-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]propan-2-one Structure

1-[4-(4-methoxy...

1-(4-methoxyphenyl)-2-(6-methylpyrimidin-4-yl)sulfanylethanone Structure

1-(4-methoxyphe...

~45%

2,5-Bis(4-methoxyphenyl)-1,4-dithiin Structure

2,5-Bis(4-metho...

1-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]propan-2-one Structure

1-[4-(4-methoxy...

Thermal and photochemical rearrangements of 1, 4-dithiin sul...

[Kobayashi, Keiji; Mutai, Kiyoshi Tetrahedron Letters, 1981 , vol. 22, # 51 p. 5201 - 5204]

SKELETAL REARRANGEMENT OF 2, 5-DIARYL-1, 4-DITHIIN-1-OXIDES ...

[Kobayashi, Keiji; Mutai, Kiyoshi Chemistry Letters, 1981 , p. 1105 - 1108]