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

Bromine analogs of quinoxidine, dioxidine, and amides of di-N-oxides of 3-hydroxymethylquinoxaline-2-carboxylic acid

…, NP Solov'eva, LM Polukhina, NY Moskalenko…

Index: Musatova, I. S.; Elina, A. S.; Solov'eva, N. P.; Polukhina, L. M.; Moskalenko, N. Yu.; Pershin, G. N. Pharmaceutical Chemistry Journal, 1983 , vol. 17, # 11 p. 779 - 784 Khimiko-Farmatsevticheskii Zhurnal, 1983 , vol. 17, # 11 p. 1307 - 1312

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Citation Number: 1

Abstract

Amides of 3-hydroxymethyl-7-bromoquinoxaline-2-carboxylic acid di-N-oxide (XXIIIa-i) were synthesized from 2-carbethoxy-3-methyl-7-bromoquinoxaline-di-N-oxide(V), which was in turn prepared by a known method: the reaction of 5 (6)-bromobenzofuroxane (VI) with esters of acetoacetic acid in the presence of various basic reagents [4, 5]. These authors recommended the use of the 7-and 6-bromo isomers of 2-carbalkoxy-3-methylquinoxaline ...

5-BROMOBENZO[C][1,2,5]OXADIAZOLE 1-OXIDE Structure

5-BROMOBENZO[C]...

Ethyl acetoacetate Structure

Ethyl acetoacetate

~%

ethyl 6-bromo-3-methylquinoxaline-2-carboxylate Structure

ethyl 6-bromo-3...

ethyl 7-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylate Structure

ethyl 7-bromo-3...

Detail

2-Carbethoxy-3-methyl-7-bromoquinoxaline-di-N-oxide Structure

2-Carbethoxy-3-...

~58%

7-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylic acid Structure

7-bromo-3-methy...

5-BROMOBENZO[C][1,2,5]OXADIAZOLE 1-OXIDE Structure

5-BROMOBENZO[C]...

~%

7-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylic acid Structure

7-bromo-3-methy...

Methanol Structure

7-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylic acid Structure

7-bromo-3-methy...

~76%

methyl 7-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylate Structure

methyl 7-bromo-...

5-BROMOBENZO[C][1,2,5]OXADIAZOLE 1-OXIDE Structure

5-BROMOBENZO[C]...

~%

methyl 7-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylate Structure

methyl 7-bromo-...

2-Carbethoxy-3-methyl-7-bromoquinoxaline-di-N-oxide Structure

2-Carbethoxy-3-...

~%

methyl 7-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylate Structure

methyl 7-bromo-...

Ethyl acetoacetate Structure

Ethyl acetoacetate

5-fluorobenzofuroxan Structure

5-fluorobenzofuroxan

~54%

ethyl 6-fluoro-1-hydroxybenzimidazole-2-carboxylate Structure

ethyl 6-fluoro-...

ethyl 7-fluoro-3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-carboxylate Structure

ethyl 7-fluoro-...

Ethyl acetoacetate Structure

Ethyl acetoacetate

5-fluorobenzofuroxan Structure

5-fluorobenzofuroxan

~18%

ethyl 6-fluoro-1-hydroxybenzimidazole-2-carboxylate Structure

ethyl 6-fluoro-...

ethyl 7-fluoro-3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-carboxylate Structure

ethyl 7-fluoro-...

2-Carboethoxy-3-acetoxymethyl-7-bromoquinoxaline-di-N-oxide Structure

2-Carboethoxy-3...

~95%

6-bromo-9-oxido-4-oxo-1H-furo[3,4-b]quinoxalin-4-ium-3-one Structure

6-bromo-9-oxido...

5-BROMOBENZO[C][1,2,5]OXADIAZOLE 1-OXIDE Structure

5-BROMOBENZO[C]...

~%

6-bromo-9-oxido-4-oxo-1H-furo[3,4-b]quinoxalin-4-ium-3-one Structure

6-bromo-9-oxido...

2-Carboethoxy-3-bromomethyl-7-bromoquinoxaline-di-N-oxide Structure

2-Carboethoxy-3...

~%

6-bromo-9-oxido-4-oxo-1H-furo[3,4-b]quinoxalin-4-ium-3-one Structure

6-bromo-9-oxido...

2-Carbethoxy-3-methyl-7-bromoquinoxaline-di-N-oxide Structure

2-Carbethoxy-3-...

~%

6-bromo-9-oxido-4-oxo-1H-furo[3,4-b]quinoxalin-4-ium-3-one Structure

6-bromo-9-oxido...

6-bromo-9-oxido-4-oxo-1H-furo[3,4-b]quinoxalin-4-ium-3-one Structure

6-bromo-9-oxido...

~99%

7-bromo-3-(hydroxymethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-carboxamide Structure

7-bromo-3-(hydr...

5-BROMOBENZO[C][1,2,5]OXADIAZOLE 1-OXIDE Structure

5-BROMOBENZO[C]...

~%

7-bromo-3-(hydroxymethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-carboxamide Structure

7-bromo-3-(hydr...

2-Carboethoxy-3-bromomethyl-7-bromoquinoxaline-di-N-oxide Structure

2-Carboethoxy-3...

~%

7-bromo-3-(hydroxymethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-carboxamide Structure

7-bromo-3-(hydr...

2-Carboethoxy-3-acetoxymethyl-7-bromoquinoxaline-di-N-oxide Structure

2-Carboethoxy-3...

~%

7-bromo-3-(hydroxymethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-carboxamide Structure

7-bromo-3-(hydr...

2-Carbethoxy-3-methyl-7-bromoquinoxaline-di-N-oxide Structure

2-Carbethoxy-3-...

~%

7-bromo-3-(hydroxymethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-carboxamide Structure

7-bromo-3-(hydr...

2,3-Dimethyl-7(6)-bromoquinoxaline-di-N-oxide Structure

2,3-Dimethyl-7(...

~96%

6-bromo-2,3-bis(bromomethyl)-4-oxidoquinoxalin-1-ium 1-oxide Structure

6-bromo-2,3-bis...

5-BROMOBENZO[C][1,2,5]OXADIAZOLE 1-OXIDE Structure

5-BROMOBENZO[C]...

Ethyl acetoacetate Structure

Ethyl acetoacetate

~%

ethyl 7-bromo-3-methylquinoxaline-2-carboxylate Structure

ethyl 7-bromo-3...

ethyl 7-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylate Structure

ethyl 7-bromo-3...

Detail

5-BROMOBENZO[C][1,2,5]OXADIAZOLE 1-OXIDE Structure

5-BROMOBENZO[C]...

Ethyl acetoacetate Structure

Ethyl acetoacetate

~%

ethyl 6-bromo-3-methylquinoxaline-2-carboxylate Structure

ethyl 6-bromo-3...

ethyl 7-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylate Structure

ethyl 7-bromo-3...

Detail

5-BROMOBENZO[C][1,2,5]OXADIAZOLE 1-OXIDE Structure

5-BROMOBENZO[C]...

Ethyl acetoacetate Structure

Ethyl acetoacetate

~%

ethyl 7-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylate Structure

ethyl 7-bromo-3...

ethyl 6-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylate Structure

ethyl 6-bromo-3...

Detail

5-BROMOBENZO[C][1,2,5]OXADIAZOLE 1-OXIDE Structure

5-BROMOBENZO[C]...

Ethyl acetoacetate Structure

Ethyl acetoacetate

~%

ethyl 7-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylate Structure

ethyl 7-bromo-3...

ethyl 6-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylate Structure

ethyl 6-bromo-3...

Detail

5-BROMOBENZO[C][1,2,5]OXADIAZOLE 1-OXIDE Structure

5-BROMOBENZO[C]...

Ethyl acetoacetate Structure

Ethyl acetoacetate

~%

ethyl 7-bromo-3-methylquinoxaline-2-carboxylate Structure

ethyl 7-bromo-3...

ethyl 7-bromo-3-methyl-4-oxidoquinoxalin-4-ium-2-carboxylate Structure

ethyl 7-bromo-3...

Detail