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

Synthesis of 6??amino??1, 2, 3??triazolo [4, 5??c] pyridin??4 (5H) one (8??aza??3??deazaguanine) and 6??amino??1??(β??D??ribofuranosyl)??1, 2, 3??triazolo [4, 5??c] pyridin??4 (5H) …

RHB Meyer, GR Revankar, P Dan Cook…

Index: Meyer Jr.; Revankar; Cook; et al. Journal of Heterocyclic Chemistry, 1980 , vol. 17, # 1 p. 159 - 169

Full Text: HTML

Citation Number: 13

Abstract

Abstract The total synthesis of 6-amino-1, 2, 3-triazolo [4, 5-c] pyridin-4 (5H) one (8-aza-3- deazaguanine, 3) and 6-amino-1-(β-D-ribofuranosyl)-1, 2, 3-triazolo [4, 5-c] pyridin-4 (5H) one (8-aza-3-deazaguano-sine, 22) has been described for the first time by a novel base- catalyzed ring closure of 4 (5)-cyanomethyl-1, 2, 3-triazole-5 (4) carboxamide (14) and methyl 5-cyanomethyl-1-(2, 3, 5-tri-O-ben-zoyl-β-D-ribofuranosyl)-1, 2, 3-triazole-4- ...

Dimethyl 3-oxoglutarate Structure

Dimethyl 3-oxog...

~%

methyl 5-(carbamoylmethyl)-2H-triazole-4-carboxylate Structure

methyl 5-(carba...

dimethyl 3-[(2,4-dinitrophenyl)hydrazinylidene]pentanedioate Structure

dimethyl 3-[(2,...

~%

methyl 5-(carbamoylmethyl)-2H-triazole-4-carboxylate Structure

methyl 5-(carba...

Methyl 5-Methoxycarbonylmethyl-1-(2,4-dinitroanilino)-1,2,3-triazole-4-carboxylate Structure

Methyl 5-Methox...

~%

methyl 5-(carbamoylmethyl)-2H-triazole-4-carboxylate Structure

methyl 5-(carba...

Methyl 4(5)Methoxycarbonylmethyl-1,2,3-triazole-5(4)carboxylate Structure

Methyl 4(5)Meth...

~99%

methyl 5-(carbamoylmethyl)-2H-triazole-4-carboxylate Structure

methyl 5-(carba...

Methyl 4(5)Methoxycarbonylmethyl-1,2,3-triazole-5(4)carboxylate Structure

Methyl 4(5)Meth...

~56%

4(5)Carbamoylmethyl-1,2,3-triazole-5(4)carboxamide Structure

4(5)Carbamoylme...

methyl 5-(carbamoylmethyl)-2H-triazole-4-carboxylate Structure

methyl 5-(carba...

Dimethyl 3-oxoglutarate Structure

Dimethyl 3-oxog...

2,4-Dinitrophenylhydrazine Structure

2,4-Dinitrophen...

~89%

dimethyl 3-[(2,4-dinitrophenyl)hydrazinylidene]pentanedioate Structure

dimethyl 3-[(2,...

Methyl 5-Cyanomethyl-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,3-triazole-4-carboxylate Structure

Methyl 5-Cyanom...

~37%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-1,5-dihydro-1-b-D-ribofuranosyl- Structure

4H-1,2,3-Triazo...

dimethyl 3-[(2,4-dinitrophenyl)hydrazinylidene]pentanedioate Structure

dimethyl 3-[(2,...

~%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-1,5-dihydro-1-b-D-ribofuranosyl- Structure

4H-1,2,3-Triazo...

Methyl 5-Methoxycarbonylmethyl-1-(2,4-dinitroanilino)-1,2,3-triazole-4-carboxylate Structure

Methyl 5-Methox...

~%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-1,5-dihydro-1-b-D-ribofuranosyl- Structure

4H-1,2,3-Triazo...

Methyl 4(5)Methoxycarbonylmethyl-1,2,3-triazole-5(4)carboxylate Structure

Methyl 4(5)Meth...

~%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-1,5-dihydro-1-b-D-ribofuranosyl- Structure

4H-1,2,3-Triazo...

b-D-Ribofuranose 1-acetate 2,3,5-tribenzoate Structure

b-D-Ribofuranos...

~%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-1,5-dihydro-1-b-D-ribofuranosyl- Structure

4H-1,2,3-Triazo...

1H-1,2,3-Triazole-4-carboxylicacid,5-(cyanomethyl)-,methylester(9CI) Structure

1H-1,2,3-Triazo...

~%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-1,5-dihydro-1-b-D-ribofuranosyl- Structure

4H-1,2,3-Triazo...

methyl 5-(carbamoylmethyl)-2H-triazole-4-carboxylate Structure

methyl 5-(carba...

~%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-1,5-dihydro-1-b-D-ribofuranosyl- Structure

4H-1,2,3-Triazo...

Methyl 5-Cyanomethyl-2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,3-triazole-4-carboxylate Structure

Methyl 5-Cyanom...

~83%

5-(cyanomethyl)-2-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]triazole-4-carboxamide Structure

5-(cyanomethyl)...

Dimethyl 3-oxoglutarate Structure

Dimethyl 3-oxog...

~%

5-(cyanomethyl)-2-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]triazole-4-carboxamide Structure

5-(cyanomethyl)...

dimethyl 3-[(2,4-dinitrophenyl)hydrazinylidene]pentanedioate Structure

dimethyl 3-[(2,...

~%

5-(cyanomethyl)-2-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]triazole-4-carboxamide Structure

5-(cyanomethyl)...

Methyl 5-Methoxycarbonylmethyl-1-(2,4-dinitroanilino)-1,2,3-triazole-4-carboxylate Structure

Methyl 5-Methox...

~%

5-(cyanomethyl)-2-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]triazole-4-carboxamide Structure

5-(cyanomethyl)...

Methyl 4(5)Methoxycarbonylmethyl-1,2,3-triazole-5(4)carboxylate Structure

Methyl 4(5)Meth...

~%

5-(cyanomethyl)-2-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]triazole-4-carboxamide Structure

5-(cyanomethyl)...

b-D-Ribofuranose 1-acetate 2,3,5-tribenzoate Structure

b-D-Ribofuranos...

~%

5-(cyanomethyl)-2-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]triazole-4-carboxamide Structure

5-(cyanomethyl)...

1H-1,2,3-Triazole-4-carboxylicacid,5-(cyanomethyl)-,methylester(9CI) Structure

1H-1,2,3-Triazo...

~%

5-(cyanomethyl)-2-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]triazole-4-carboxamide Structure

5-(cyanomethyl)...

methyl 5-(carbamoylmethyl)-2H-triazole-4-carboxylate Structure

methyl 5-(carba...

~%

5-(cyanomethyl)-2-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]triazole-4-carboxamide Structure

5-(cyanomethyl)...

Dimethyl 3-oxoglutarate Structure

Dimethyl 3-oxog...

~%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-3,5-dihydro- Structure

4H-1,2,3-Triazo...

dimethyl 3-[(2,4-dinitrophenyl)hydrazinylidene]pentanedioate Structure

dimethyl 3-[(2,...

~%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-3,5-dihydro- Structure

4H-1,2,3-Triazo...

Methyl 5-Methoxycarbonylmethyl-1-(2,4-dinitroanilino)-1,2,3-triazole-4-carboxylate Structure

Methyl 5-Methox...

~%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-3,5-dihydro- Structure

4H-1,2,3-Triazo...

1H-1,2,3-Triazole-4-carboxylicacid,5-(cyanomethyl)-,methylester(9CI) Structure

1H-1,2,3-Triazo...

~17%

1H-1,2,3-Triazole-4-carboxamide,5-(cyanomethyl)-(9CI) Structure

1H-1,2,3-Triazo...

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-3,5-dihydro- Structure

4H-1,2,3-Triazo...

1H-1,2,3-Triazole-4-carboxamide,5-(cyanomethyl)-(9CI) Structure

1H-1,2,3-Triazo...

~58%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-3,5-dihydro- Structure

4H-1,2,3-Triazo...

Methyl 4(5)Methoxycarbonylmethyl-1,2,3-triazole-5(4)carboxylate Structure

Methyl 4(5)Meth...

~%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-3,5-dihydro- Structure

4H-1,2,3-Triazo...

methyl 5-(carbamoylmethyl)-2H-triazole-4-carboxylate Structure

methyl 5-(carba...

~%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-3,5-dihydro- Structure

4H-1,2,3-Triazo...

1H-1,2,3-Triazole-4-carboxylicacid,5-(cyanomethyl)-,methylester(9CI) Structure

1H-1,2,3-Triazo...

~%

4H-1,2,3-Triazolo[4,5-c]pyridin-4-one,6-amino-3,5-dihydro- Structure

4H-1,2,3-Triazo...