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

Synthesis of 1, 2, 3, 4-tetrahydroisoquinolines containing electron-withdrawing groups

GJ Quallich, TW Makowski, AF Sanders…

Index: Quallich, George J.; Makowski, Teresa W.; Sanders, Andrew F.; Urban, Frank J.; Vazquez, Enrique Journal of Organic Chemistry, 1998 , vol. 63, # 12 p. 4116 - 4119

Full Text: HTML

Citation Number: 38

Abstract

Synthesis of tetrahydroisoquinolines containing electronwithdrawing groups in the aryl ring was required for the preparation of novel pharmaceutical agents. Unfortunately, many of the isoquinoline (Pomeranz-Fritsch) 1, dihydroisoquinoline (Bischler-Napieralski), 2 and ...

2-(2-(HYDROXYMETHYL)-5-NITROPHENYL)ETHANOLDIMESYLATE Structure

2-(2-(HYDROXYME...

~%

6-Nitro-1,2,3,4-tetrahydro-isoquinoline Structure

6-Nitro-1,2,3,4...

2-Chloro-4-nitrobenzoic acid Structure

2-Chloro-4-nitr...

~%

6-Nitro-1,2,3,4-tetrahydro-isoquinoline Structure

6-Nitro-1,2,3,4...

2-(Carboxymethyl)-4-nitrobenzoic acid Structure

2-(Carboxymethy...

~%

6-Nitro-1,2,3,4-tetrahydro-isoquinoline Structure

6-Nitro-1,2,3,4...

2-(2-(HYDROXYMETHYL)-5-NITROPHENYL)-ETHANOL Structure

2-(2-(HYDROXYME...

~%

6-Nitro-1,2,3,4-tetrahydro-isoquinoline Structure

6-Nitro-1,2,3,4...

2-(2-carboxy-5-nitrophenyl)malonic acid Structure

2-(2-carboxy-5-...

~%

6-Nitro-1,2,3,4-tetrahydro-isoquinoline Structure

6-Nitro-1,2,3,4...

2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-4-nitrobenzoic acid Structure

2-(1,3-dimethox...

~%

6-Nitro-1,2,3,4-tetrahydro-isoquinoline Structure

6-Nitro-1,2,3,4...

2-(Carboxymethyl)-4-nitrobenzoic acid Structure

2-(Carboxymethy...

~89%

2-(2-(HYDROXYMETHYL)-5-NITROPHENYL)-ETHANOL Structure

2-(2-(HYDROXYME...

2-Chloro-4-nitrobenzoic acid Structure

2-Chloro-4-nitr...

~%

2-(2-(HYDROXYMETHYL)-5-NITROPHENYL)-ETHANOL Structure

2-(2-(HYDROXYME...

2-(2-carboxy-5-nitrophenyl)malonic acid Structure

2-(2-carboxy-5-...

~%

2-(2-(HYDROXYMETHYL)-5-NITROPHENYL)-ETHANOL Structure

2-(2-(HYDROXYME...

2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-4-nitrobenzoic acid Structure

2-(1,3-dimethox...

~%

2-(2-(HYDROXYMETHYL)-5-NITROPHENYL)-ETHANOL Structure

2-(2-(HYDROXYME...

2-Chloro-4-nitrobenzoic acid Structure

2-Chloro-4-nitr...

Dimethyl malonate Structure

Dimethyl malonate

~71%

2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-4-nitrobenzoic acid Structure

2-(1,3-dimethox...

2-Chloro-4-nitrobenzoic acid Structure

2-Chloro-4-nitr...

Diethyl malonate Structure

Diethyl malonate

~0%

2-(1,3-diethoxy-1,3-dioxopropan-2-yl)-4-nitrobenzoic acid Structure

2-(1,3-diethoxy...

2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-4-nitrobenzoic acid Structure

2-(1,3-dimethox...

2-Chloro-4-nitrobenzoic acid Structure

2-Chloro-4-nitr...

~%

2-(Carboxymethyl)-4-nitrobenzoic acid Structure

2-(Carboxymethy...

2-(2-carboxy-5-nitrophenyl)malonic acid Structure

2-(2-carboxy-5-...

~%

2-(Carboxymethyl)-4-nitrobenzoic acid Structure

2-(Carboxymethy...

2-Chloro-4-nitrobenzoic acid Structure

2-Chloro-4-nitr...

Sodium Methylate Structure

Sodium Methylate

Diethyl malonate Structure

Diethyl malonate

~%

2-(1,3-diethoxy-1,3-dioxopropan-2-yl)-4-nitrobenzoic acid Structure

2-(1,3-diethoxy...

Detail

2-Chloro-4-nitrobenzoic acid Structure

2-Chloro-4-nitr...

~%

2-(2-(HYDROXYMETHYL)-5-NITROPHENYL)ETHANOLDIMESYLATE Structure

2-(2-(HYDROXYME...

2-(Carboxymethyl)-4-nitrobenzoic acid Structure

2-(Carboxymethy...

~%

2-(2-(HYDROXYMETHYL)-5-NITROPHENYL)ETHANOLDIMESYLATE Structure

2-(2-(HYDROXYME...

2-(2-carboxy-5-nitrophenyl)malonic acid Structure

2-(2-carboxy-5-...

~%

2-(2-(HYDROXYMETHYL)-5-NITROPHENYL)ETHANOLDIMESYLATE Structure

2-(2-(HYDROXYME...

2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-4-nitrobenzoic acid Structure

2-(1,3-dimethox...

~%

2-(2-(HYDROXYMETHYL)-5-NITROPHENYL)ETHANOLDIMESYLATE Structure

2-(2-(HYDROXYME...

2-Chloro-4-nitrobenzoic acid Structure

2-Chloro-4-nitr...

~%

6-nitro-3,4-dihydro-1H-isochromene Structure

6-nitro-3,4-dih...

2-(Carboxymethyl)-4-nitrobenzoic acid Structure

2-(Carboxymethy...

~%

6-nitro-3,4-dihydro-1H-isochromene Structure

6-nitro-3,4-dih...

2-(2-carboxy-5-nitrophenyl)malonic acid Structure

2-(2-carboxy-5-...

~%

6-nitro-3,4-dihydro-1H-isochromene Structure

6-nitro-3,4-dih...

2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-4-nitrobenzoic acid Structure

2-(1,3-dimethox...

~%

6-nitro-3,4-dihydro-1H-isochromene Structure

6-nitro-3,4-dih...

2,5-Dibromobenzoic acid Structure

2,5-Dibromobenz...

~%

5-Bromo-2-(carboxymethyl)benzoic acid Structure

5-Bromo-2-(carb...

2-(4-bromo-2-carboxyphenyl)malonic acid dimethyl ester Structure

2-(4-bromo-2-ca...

~%

5-Bromo-2-(carboxymethyl)benzoic acid Structure

5-Bromo-2-(carb...

2-Chloro-5-(trifluoromethyl)benzoic acid Structure

2-Chloro-5-(tri...

~%

2-carboxymethyl-5-trifluoromethyl-benzoic acid Structure

2-carboxymethyl...

5-trifluoromethyl-2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)benzoic acid Structure

5-trifluorometh...

~%

2-carboxymethyl-5-trifluoromethyl-benzoic acid Structure

2-carboxymethyl...

Synthesis and flow cytometric evaluation of novel 1, 2, 3, 4...

[Zhu, Zhengxiang; Furr, John; Buolamwini, John K. Journal of Medicinal Chemistry, 2003 , vol. 46, # 5 p. 831 - 837]

Synthesis and flow cytometric evaluation of novel 1, 2, 3, 4...

[Zhu, Zhengxiang; Furr, John; Buolamwini, John K. Journal of Medicinal Chemistry, 2003 , vol. 46, # 5 p. 831 - 837]

Synthesis and flow cytometric evaluation of novel 1, 2, 3, 4...

[Zhu, Zhengxiang; Furr, John; Buolamwini, John K. Journal of Medicinal Chemistry, 2003 , vol. 46, # 5 p. 831 - 837]

Synthesis and flow cytometric evaluation of novel 1, 2, 3, 4...

[Zhu, Zhengxiang; Furr, John; Buolamwini, John K. Journal of Medicinal Chemistry, 2003 , vol. 46, # 5 p. 831 - 837]

Synthesis and flow cytometric evaluation of novel 1, 2, 3, 4...

[Zhu, Zhengxiang; Furr, John; Buolamwini, John K. Journal of Medicinal Chemistry, 2003 , vol. 46, # 5 p. 831 - 837]