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

Reaction of 4??Amino??1, 2, 4??triazines with phosphorus pentasulfide. Deamination during aromatization

MM Eid, MA Badawy, MAH Ghazala…

Index: Eid, M. M.; Badawy, M. A.; Ghazala, M. A. H.; Ibrahim, Yehia A. Journal of Heterocyclic Chemistry, 1983 , vol. 20, p. 1709 - 1711

Full Text: HTML

Citation Number: 13

Abstract

Abstract Synthesis of several derivatives of thieno [2, 3-e]-1, 2, 4-triazines has been achieved via the action of phosphorus pentasulfide on 6-vinyl-or 6-acylmethyl-5-oxo-1, 2, 4- triazine derivatives. During these investigations interesting synthetically useful functions for phosphorus pentasulfide in pyridine were observed, among which the deamination of certain N-amino heterocycles is unprecedented.

6-styryl-2,3,4,5-tetrahydro-3-thioxo-1,2,4-triazin-5-one Structure

6-styryl-2,3,4,...

~67%

6-phenyl-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-phenyl-2H-thi...

N/A Structure

~61%

6-phenyl-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-phenyl-2H-thi...

6-phenacyl-3-sulfanylidene-2H-1,2,4-triazin-5-one Structure

6-phenacyl-3-su...

~60%

6-phenyl-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-phenyl-2H-thi...

4-(benzylideneamino)-3-mercapto-6-styryl-1,2,4-triazin-5(4H)-one Structure

4-(benzylidenea...

~56%

6-phenyl-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-phenyl-2H-thi...

N/A Structure

~34%

Thieno[2,3-e]-1,2,4-triazine,3-(methylthio)-6-phenyl- Structure

Thieno[2,3-e]-1...

6-phenyl-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-phenyl-2H-thi...

bpa Structure

~%

6-phenyl-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-phenyl-2H-thi...

Ethyl 4-phenyl-2,4-dioxobutyrate Structure

Ethyl 4-phenyl-...

~%

6-phenyl-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-phenyl-2H-thi...

N/A Structure

~%

6-phenyl-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-phenyl-2H-thi...

6-β-(4-methoxyphenyl)vinyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one Structure

6-β-(4-methoxyp...

~65%

6-(4-methoxyphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methoxyphe...

3-Mercapto-6-[2-(4-methoxy-phenyl)-2-oxo-ethyl]-2H-[1,2,4]triazin-5-one Structure

3-Mercapto-6-[2...

~62%

6-(4-methoxyphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methoxyphe...

4-amino-3-(methylthio)-6-(4-methoxystyryl)-1,2,4-triazin-5(4H)-one Structure

4-amino-3-(meth...

~30%

6-(4-methoxyphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methoxyphe...

6-(4-methoxyphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methoxyphe...

4-amino-3,4-dihydro-6-(4-methoxystyryl)-3-thioxo-1,2,4-triazin-5(2H)-one Structure

4-amino-3,4-dih...

~%

6-(4-methoxyphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methoxyphe...

4-(4-Methoxy-phenyl)-2,4-dioxo-butyric acid Structure

4-(4-Methoxy-ph...

~%

6-(4-methoxyphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methoxyphe...

Ethyl 4-[4-methoxyphenyl]-2,4-dioxobutyrate Structure

Ethyl 4-[4-meth...

~%

6-(4-methoxyphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methoxyphe...

N/A Structure

~8%

Thieno[2,3-e]-1,2,4-triazine,3-(methylthio)-6-phenyl- Structure

Thieno[2,3-e]-1...

6-phenyl-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-phenyl-2H-thi...

6-β-p-tolylvinyl-3-mercapto-5-oxo-2,5-dihydro-1,2,4-triazine Structure

6-β-p-tolylviny...

~73%

6-(4-methylphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methylphen...

4-amino-6-p-methylstyryl-2,3-dihydro-3-thioxo-1,2,4-triazin-5(4H)-one Structure

4-amino-6-p-met...

~71%

6-(4-methylphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methylphen...

3-mercapto-6-(2-oxo-2-(p-tolyl)ethyl)-1,2,4-triazin-5(2H)-one Structure

3-mercapto-6-(2...

~72%

6-(4-methylphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methylphen...

4-amino-6-(4-methylstyryl)-3-(methylthio)-1,2,4-triazin-5(4H)-one Structure

4-amino-6-(4-me...

~38%

6-(4-methylphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methylphen...

6-(4-methylphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methylphen...

Ethyl 4-(4-methylphenyl)-2,4-dioxobutanoate Structure

Ethyl 4-(4-meth...

~%

6-(4-methylphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methylphen...

(E)-2-oxo-4-p-tolylbut-3-enoic acid Structure

(E)-2-oxo-4-p-t...

~%

6-(4-methylphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methylphen...

bpa Structure

~%

Thieno[2,3-e]-1,2,4-triazine,3-(methylthio)-6-phenyl- Structure

Thieno[2,3-e]-1...

Ethyl 4-phenyl-2,4-dioxobutyrate Structure

Ethyl 4-phenyl-...

~%

Thieno[2,3-e]-1,2,4-triazine,3-(methylthio)-6-phenyl- Structure

Thieno[2,3-e]-1...

6-styryl-2,3,4,5-tetrahydro-3-thioxo-1,2,4-triazin-5-one Structure

6-styryl-2,3,4,...

~%

Thieno[2,3-e]-1,2,4-triazine,3-(methylthio)-6-phenyl- Structure

Thieno[2,3-e]-1...

N/A Structure

~%

Thieno[2,3-e]-1,2,4-triazine,3-(methylthio)-6-phenyl- Structure

Thieno[2,3-e]-1...

6-phenacyl-3-sulfanylidene-2H-1,2,4-triazin-5-one Structure

6-phenacyl-3-su...

~%

Thieno[2,3-e]-1,2,4-triazine,3-(methylthio)-6-phenyl- Structure

Thieno[2,3-e]-1...

N/A Structure

~%

Thieno[2,3-e]-1,2,4-triazine,3-(methylthio)-6-phenyl- Structure

Thieno[2,3-e]-1...

N/A Structure

~%

Thieno[2,3-e]-1,2,4-triazine,3-(methylthio)-6-phenyl- Structure

Thieno[2,3-e]-1...

4-(benzylideneamino)-3-mercapto-6-styryl-1,2,4-triazin-5(4H)-one Structure

4-(benzylidenea...

~%

Thieno[2,3-e]-1,2,4-triazine,3-(methylthio)-6-phenyl- Structure

Thieno[2,3-e]-1...

6-phenyl-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-phenyl-2H-thi...

methyl iodide Structure

~%

Thieno[2,3-e]-1,2,4-triazine,3-(methylthio)-6-phenyl- Structure

Thieno[2,3-e]-1...

4-amino-6-(4-methylstyryl)-3-(methylthio)-1,2,4-triazin-5(4H)-one Structure

4-amino-6-(4-me...

~10%

6-(4-methylphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methylphen...

6-(4-methylphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methylphen...

Ethyl 4-(4-methylphenyl)-2,4-dioxobutanoate Structure

Ethyl 4-(4-meth...

~%

6-(4-methylphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methylphen...

6-β-p-tolylvinyl-3-mercapto-5-oxo-2,5-dihydro-1,2,4-triazine Structure

6-β-p-tolylviny...

~%

6-(4-methylphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methylphen...

4-amino-6-p-methylstyryl-2,3-dihydro-3-thioxo-1,2,4-triazin-5(4H)-one Structure

4-amino-6-p-met...

~%

6-(4-methylphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methylphen...

3-mercapto-6-(2-oxo-2-(p-tolyl)ethyl)-1,2,4-triazin-5(2H)-one Structure

3-mercapto-6-(2...

~%

6-(4-methylphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methylphen...

4-amino-6-(4-methylstyryl)-3-(methylthio)-1,2,4-triazin-5(4H)-one Structure

4-amino-6-(4-me...

~%

6-(4-methylphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methylphen...

(E)-2-oxo-4-p-tolylbut-3-enoic acid Structure

(E)-2-oxo-4-p-t...

~%

6-(4-methylphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methylphen...

6-(4-methylphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methylphen...

methyl iodide Structure

~%

6-(4-methylphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methylphen...

N/A Structure

~66%

6-(4-methoxyphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methoxyphe...

4-amino-3-(methylthio)-6-(4-methoxystyryl)-1,2,4-triazin-5(4H)-one Structure

4-amino-3-(meth...

~8%

6-(4-methoxyphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methoxyphe...

6-(4-methoxyphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methoxyphe...

Ethyl 4-[4-methoxyphenyl]-2,4-dioxobutyrate Structure

Ethyl 4-[4-meth...

~%

6-(4-methoxyphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methoxyphe...

4-(4-Methoxy-phenyl)-2,4-dioxo-butyric acid Structure

4-(4-Methoxy-ph...

~%

6-(4-methoxyphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methoxyphe...

6-β-(4-methoxyphenyl)vinyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one Structure

6-β-(4-methoxyp...

~%

6-(4-methoxyphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methoxyphe...

4-amino-3,4-dihydro-6-(4-methoxystyryl)-3-thioxo-1,2,4-triazin-5(2H)-one Structure

4-amino-3,4-dih...

~%

6-(4-methoxyphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methoxyphe...

3-Mercapto-6-[2-(4-methoxy-phenyl)-2-oxo-ethyl]-2H-[1,2,4]triazin-5-one Structure

3-Mercapto-6-[2...

~%

6-(4-methoxyphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methoxyphe...

4-amino-3-(methylthio)-6-(4-methoxystyryl)-1,2,4-triazin-5(4H)-one Structure

4-amino-3-(meth...

~%

6-(4-methoxyphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methoxyphe...

6-(4-methoxyphenyl)-2H-thieno[2,3-e][1,2,4]triazine-3-thione Structure

6-(4-methoxyphe...

methyl iodide Structure

~%

6-(4-methoxyphenyl)-3-methylsulfanylthieno[2,3-e][1,2,4]triazine Structure

6-(4-methoxyphe...