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

The Journal of Organic Chemistry

Thiadiazoles. IV. 4-Ureido-and 4-Amino-1, 2, 5-thiadiazole-3-carboxylic Acid Derivatives from [1, 2, 5] Thiadiazolo [3, 4-d] pyrimidine-5, 7 (4H, 6H)-diones1

YF Shealy, JD Clayton

Index: Shealy,Y.F.; Clayton,J.D. Journal of Organic Chemistry, 1964 , vol. 29, p. 2141 - 2145

Full Text: HTML

Citation Number: 8

Abstract

Three thiadiazoles were isolated, depending on reaction conditions, from reactions of I11 with benzylamine. Treatment of I11 with refluxing benzylamine for 6.5 hr. resulted in the formation of 4-amino-N-benzyl-l12, 5-thiadiazole-3-carboxamide (XI); the byproduct, N, N'- dibenzylurea, was also isolated in high yield. N-Benzyl-4-(3-benz ylureido)-1, 2, 5- thiadiazole-3-carboxamide (Xa) was isolated following interaction of I11 and refluxing ...

[1,2,5]Thiadiazolo[3,4-d]pyrimidine-5,7 (3H,6H)-dione Structure

[1,2,5]Thiadiaz...

~%

[4-(hydrazinecarbonyl)-1,2,5-thiadiazol-3-yl]urea Structure

[4-(hydrazineca...

[1,2,5]Thiadiazolo[3,4-d]pyrimidine-5,7(4H,6H)- dione,4,6-dimethyl- Structure

[1,2,5]Thiadiaz...

~%

N-methyl-4-methylamino-1,2,5-thiadiazole-3-carboxamide Structure

N-methyl-4-meth...

N-methyl-4-methylamino-1,2,5-thiadiazole-3-carboxamide Structure

N-methyl-4-meth...

~%

4-Amino-1,2,5-thiadiazole-3-carboxylic acid Structure

4-Amino-1,2,5-t...

1,2,5-Thiadiazole-3-carboxylicacid, 4-[(aminocarbonyl)amino]- Structure

1,2,5-Thiadiazo...

~%

4-Amino-1,2,5-thiadiazole-3-carboxylic acid Structure

4-Amino-1,2,5-t...

[1,2,5]Thiadiazolo[3,4-d]pyrimidine-5,7 (3H,6H)-dione Structure

[1,2,5]Thiadiaz...

Benzylamine Structure

~%

N-benzyl-4-(carbamoylamino)-1,2,5-thiadiazole-3-carboxamide Structure

N-benzyl-4-(car...

Benzylamine Structure

~%

N-benzyl-4-(benzylcarbamoylamino)-1,2,5-thiadiazole-3-carboxamide Structure

N-benzyl-4-(ben...

[1,2,5]Thiadiazolo[3,4-d]pyrimidine-5,7 (3H,6H)-dione Structure

[1,2,5]Thiadiaz...

Benzylamine Structure

~%

N-benzyl-4-(benzylcarbamoylamino)-1,2,5-thiadiazole-3-carboxamide Structure

N-benzyl-4-(ben...

N-benzyl-4-(carbamoylamino)-1,2,5-thiadiazole-3-carboxamide Structure

N-benzyl-4-(car...

Benzylamine Structure

~%

N-benzyl-4-(benzylcarbamoylamino)-1,2,5-thiadiazole-3-carboxamide Structure

N-benzyl-4-(ben...

Pyrrolidine Structure

[1,2,5]Thiadiazolo[3,4-d]pyrimidine-5,7 (3H,6H)-dione Structure

[1,2,5]Thiadiaz...

~%

N-[4-(pyrrolidine-1-carbonyl)-1,2,5-thiadiazol-3-yl]pyrrolidine-1-carboxamide Structure

N-[4-(pyrrolidi...

1,2,5-Thiadiazole-3-carboxamide,4-[(aminocarbonyl)amino]-N-butyl- Structure

1,2,5-Thiadiazo...

~%

[1,2,5]Thiadiazolo[3,4-d]pyrimidine-5,7 (3H,6H)-dione Structure

[1,2,5]Thiadiaz...

[1,2,5]Thiadiazolo[3,4-d]pyrimidine-5,7 (3H,6H)-dione Structure

[1,2,5]Thiadiaz...

Ethylamine Structure

~%

4-(carbamoylamino)-N-ethyl-1,2,5-thiadiazole-3-carboxamide Structure

4-(carbamoylami...

1,2,5-Thiadiazole-3-carboxamide,4-amino- Structure

1,2,5-Thiadiazo...

Ethyl isocyanate Structure

Ethyl isocyanate

~%

4-(ethylcarbamoylamino)-1,2,5-thiadiazole-3-carboxamide Structure

4-(ethylcarbamo...

1,2,5-Thiadiazole-3-carboxamide,4-[(aminocarbonyl)amino]-N-butyl- Structure

1,2,5-Thiadiazo...

~%

1,2,5-Thiadiazole-3-carboxamide,4-amino-N-butyl- Structure

1,2,5-Thiadiazo...

[1,2,5]Thiadiazolo[3,4-d]pyrimidine-5,7 (3H,6H)-dione Structure

[1,2,5]Thiadiaz...

~%

1,2,5-Thiadiazole-3-carboxylicacid, 4-[(aminocarbonyl)amino]- Structure

1,2,5-Thiadiazo...

1,2,5-Thiadiazole-3-carboxamide,4-[(aminocarbonyl)amino]-N-butyl- Structure

1,2,5-Thiadiazo...

~%

1,2,5-Thiadiazole-3-carboxylicacid, 4-[(aminocarbonyl)amino]- Structure

1,2,5-Thiadiazo...

[1,2,5]Thiadiazolo[3,4-d]pyrimidine-5,7 (3H,6H)-dione Structure

[1,2,5]Thiadiaz...

n-butylamine Structure

~%

1,2,5-Thiadiazole-3-carboxamide,4-[(aminocarbonyl)amino]-N-butyl- Structure

1,2,5-Thiadiazo...

[1,2,5]Thiadiazolo[3,4-d]pyrimidine-5,7 (3H,6H)-dione Structure

[1,2,5]Thiadiaz...

~%

1,2,5-Thiadiazole-3-carboxylicacid, 4-amino-, hydrazide Structure

1,2,5-Thiadiazo...

1,2,5-Thiadiazole-3-carboxylicacid, 4-[(aminocarbonyl)amino]- Structure

1,2,5-Thiadiazo...

~%

1,2,5-Thiadiazole-3-carboxylicacid, 4-amino-, hydrazide Structure

1,2,5-Thiadiazo...