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

Organic letters

Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; synthesis of dimebolin

H Dong, RT Latka, TG Driver

Index: Dong, Huijun; Latka, Regina T.; Driver, Tom G. Organic Letters, 2011 , vol. 13, # 10 p. 2726 - 2729

Full Text: HTML

Citation Number: 39

Abstract

A range of γ-carbolines were produced stereoselectively from ruthenium (III)-catalyzed reactions of 3-pyridyl substituted aryl azides. Other catalysts and conditions were neither as selective nor as high-yielding. This method was used to synthesize dimebolin in a concise and efficient manner.

8-methoxy-2-methyl-5H-pyrido[4,3-b]indol-2-ium trifluoromethanesulfonate Structure

8-methoxy-2-met...

~%

8-Methoxy-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole Structure

8-Methoxy-2-met...

1-methyl-3-(2-azido-5-methoxyphenyl)pyridinium triflate Structure

1-methyl-3-(2-a...

~%

8-Methoxy-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole Structure

8-Methoxy-2-met...

4-methoxy-2-pyridin-3-ylaniline Structure

4-methoxy-2-pyr...

~%

8-Methoxy-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole Structure

8-Methoxy-2-met...

2-Bromo-4-methoxyaniline Structure

2-Bromo-4-metho...

~%

8-Methoxy-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole Structure

8-Methoxy-2-met...

3-Pyridylboronic acid Structure

3-Pyridylboroni...

~%

8-Methoxy-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole Structure

8-Methoxy-2-met...

2,8-dimethyl-5H-pyrido[4,3-b]indol-2-ium trifluoromethanesulfonate Structure

2,8-dimethyl-5H...

~%

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole Structure

2,8-Dimethyl-2,...

2-benzyl-8-methyl-5H-pyrido[4,3-b]indol-2-ium bromide Structure

2-benzyl-8-meth...

~%

2-benzyl-8-methyl-1,3,4,5-tetrahydropyrido[4,3-b]indole Structure

2-benzyl-8-meth...

3-(2-azido-5-methylphenyl)pyridine Structure

3-(2-azido-5-me...

~%

2-benzyl-8-methyl-1,3,4,5-tetrahydropyrido[4,3-b]indole Structure

2-benzyl-8-meth...

3-(2-azido-5-methylphenyl)-1-benzylpyridin-1-ium bromide Structure

3-(2-azido-5-me...

~%

2-benzyl-8-methyl-1,3,4,5-tetrahydropyrido[4,3-b]indole Structure

2-benzyl-8-meth...

3-(2-amino-5-methylphenyl)pyridine Structure

3-(2-amino-5-me...

~%

2-benzyl-8-methyl-1,3,4,5-tetrahydropyrido[4,3-b]indole Structure

2-benzyl-8-meth...

2-Bromo-p-toluidine Structure

2-Bromo-p-toluidine

~%

2-benzyl-8-methyl-1,3,4,5-tetrahydropyrido[4,3-b]indole Structure

2-benzyl-8-meth...

3-Pyridylboronic acid Structure

3-Pyridylboroni...

~%

2-benzyl-8-methyl-1,3,4,5-tetrahydropyrido[4,3-b]indole Structure

2-benzyl-8-meth...

8-fluoro-2-methyl-5H-pyrido[4,3-b]indol-2-ium trifluoromethanesulfonate Structure

8-fluoro-2-meth...

~%

8-Fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole Structure

8-Fluoro-2-meth...

3-(2-azido-5-fluorophenyl)pyridine Structure

3-(2-azido-5-fl...

~%

8-Fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole Structure

8-Fluoro-2-meth...

1-methyl-3-(2-azido-5-fluorophenyl)pyridinium triflate Structure

1-methyl-3-(2-a...

~%

8-Fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole Structure

8-Fluoro-2-meth...

2-Bromo-4-fluoroaniline Structure

2-Bromo-4-fluor...

~%

8-Fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole Structure

8-Fluoro-2-meth...

3-Pyridylboronic acid Structure

3-Pyridylboroni...

~%

8-Fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole Structure

8-Fluoro-2-meth...

2-methyl-5H-pyrido[4,3-b]indol-2-ium trifluoromethanesulfonate Structure

2-methyl-5H-pyr...

~%

1H-Pyrido[4,3-b]indole,2,3,4,5-tetrahydro-2-methyl- Structure

1H-Pyrido[4,3-b...

2-(PYRIDIN-3-YL)ANILINE Structure

2-(PYRIDIN-3-YL...

~%

1H-Pyrido[4,3-b]indole,2,3,4,5-tetrahydro-2-methyl- Structure

1H-Pyrido[4,3-b...

1-methyl-3-(2-azidophenyl)pyridinium triflate Structure

1-methyl-3-(2-a...

~%

1H-Pyrido[4,3-b]indole,2,3,4,5-tetrahydro-2-methyl- Structure

1H-Pyrido[4,3-b...

3-(2-azidophenyl)pyridine Structure

3-(2-azidopheny...

~%

1H-Pyrido[4,3-b]indole,2,3,4,5-tetrahydro-2-methyl- Structure

1H-Pyrido[4,3-b...

3-Pyridylboronic acid Structure

3-Pyridylboroni...

~%

1H-Pyrido[4,3-b]indole,2,3,4,5-tetrahydro-2-methyl- Structure

1H-Pyrido[4,3-b...

2-Bromoaniline Structure

~%

1H-Pyrido[4,3-b]indole,2,3,4,5-tetrahydro-2-methyl- Structure

1H-Pyrido[4,3-b...

4-(2-azidophenyl)pyridine Structure

4-(2-azidopheny...

~%

2-methyltryptoline Structure

2-methyltryptoline

1-methyl-4-(2-azidophenyl)pyridinium triflate Structure

1-methyl-4-(2-a...

~%

2-methyltryptoline Structure

2-methyltryptoline

Pyridine-4-boronic acid Structure

Pyridine-4-boro...

~%

2-methyltryptoline Structure

2-methyltryptoline

2-PYRIDIN-4-YL-PHENYLAMINE Structure

2-PYRIDIN-4-YL-...

~%

2-methyltryptoline Structure

2-methyltryptoline

2-Bromoaniline Structure

~%

2-methyltryptoline Structure

2-methyltryptoline

Novel Carboline Derivatives as Potent Antifungal Lead Compou...

[Wang, Shengzheng; Wang, Yan; Liu, Wei; Liu, Na; Zhang, Yongqiang; Dong, Guoqiang; Liu, Yang; Li, Zhengang; He, Xiaomeng; Miao, Zhenyuan; Yao, Jianzhong; Li, Jian; Zhang, Wannian; Sheng, Chunquan ACS Medicinal Chemistry Letters, 2014 , vol. 5, # 5 p. 506 - 511]

Novel Carboline Derivatives as Potent Antifungal Lead Compou...

[Wang, Shengzheng; Wang, Yan; Liu, Wei; Liu, Na; Zhang, Yongqiang; Dong, Guoqiang; Liu, Yang; Li, Zhengang; He, Xiaomeng; Miao, Zhenyuan; Yao, Jianzhong; Li, Jian; Zhang, Wannian; Sheng, Chunquan ACS Medicinal Chemistry Letters, 2014 , vol. 5, # 5 p. 506 - 511]