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

Tetrahedron

The preparation and some chemistry of 2, 2-dimethyl-1, 2-dihydroquinolines

NM Williamson, AD Ward

Index: Williamson, Natalie M.; Ward, A. David Tetrahedron, 2005 , vol. 61, # 1 p. 155 - 165

Full Text: HTML

Citation Number: 23

Abstract

The cyclisation of N-(1, 1-dimethylpropargyl) anilines, using cuprous chloride in refluxing toluene, yields 6-substituted-2, 2-dimethyl-1, 2-dihydroquinolines. The reactivity of the double bond in the heterocyclic ring of these products is exemplified by chlorination, to yield 6-substituted-3, 4-cis-dichloro-2, 2-dimethyl-1, 2, 3, 4-tetrahydroquinolines which can be selectively dechlorinated to provide 6-substituted-3-chloro-2, 2-dimethyl-1, 2, 3, 4- ...

2,2,6-trimethyl-1,2-dihydroquinoline Structure

2,2,6-trimethyl...

Trifluoroacetic anhydride Structure

Trifluoroacetic...

~72%

2,2,2-trifluoro-1-(2,2,6-trimethylquinolin-1-yl)ethanone Structure

2,2,2-trifluoro...

N-(1,1-Dimethyl-2-propynyl)-p-toluidine Structure

N-(1,1-Dimethyl...

~%

2,2,2-trifluoro-1-(2,2,6-trimethylquinolin-1-yl)ethanone Structure

2,2,2-trifluoro...

6-methoxy-2,2-dimethyl-1H-quinoline Structure

6-methoxy-2,2-d...

Trifluoroacetic anhydride Structure

Trifluoroacetic...

~42%

2,2,2-trifluoro-1-(6-methoxy-2,2-dimethylquinolin-1-yl)ethanone Structure

2,2,2-trifluoro...

N/A Structure

~%

2,2,2-trifluoro-1-(6-methoxy-2,2-dimethylquinolin-1-yl)ethanone Structure

2,2,2-trifluoro...

1-acetyl-2,2,6-trimethyl-1,2-dihydroquinoline Structure

1-acetyl-2,2,6-...

~14%

1-(4-hydroxy-2,2,6-trimethyl-3,4-dihydroquinolin-1-yl)ethanone Structure

1-(4-hydroxy-2,...

2,2,6-trimethyl-1,2-dihydroquinoline Structure

2,2,6-trimethyl...

~%

1-(4-hydroxy-2,2,6-trimethyl-3,4-dihydroquinolin-1-yl)ethanone Structure

1-(4-hydroxy-2,...

N-(1,1-Dimethyl-2-propynyl)-p-toluidine Structure

N-(1,1-Dimethyl...

~%

1-(4-hydroxy-2,2,6-trimethyl-3,4-dihydroquinolin-1-yl)ethanone Structure

1-(4-hydroxy-2,...

2,2,6-trimethyl-1,2-dihydroquinoline Structure

2,2,6-trimethyl...

~%

1-(3-chloro-2,2,6-trimethylquinolin-1-yl)ethanone Structure

1-(3-chloro-2,2...

N-(1,1-Dimethyl-2-propynyl)-p-toluidine Structure

N-(1,1-Dimethyl...

~%

1-(3-chloro-2,2,6-trimethylquinolin-1-yl)ethanone Structure

1-(3-chloro-2,2...

1-acetyl-2,2,6-trimethyl-1,2-dihydroquinoline Structure

1-acetyl-2,2,6-...

~%

1-(3-chloro-2,2,6-trimethylquinolin-1-yl)ethanone Structure

1-(3-chloro-2,2...

6-bromo-2,2-dimethyl-1,2-dihydroquinoline Structure

6-bromo-2,2-dim...

Trifluoroacetic anhydride Structure

Trifluoroacetic...

~88%

1-(6-bromo-2,2-dimethylquinolin-1-yl)-2,2,2-trifluoroethanone Structure

1-(6-bromo-2,2-...

4-bromo-N-(2-methylbut-3-yn-2-yl)benzenamine Structure

4-bromo-N-(2-me...

~%

1-(6-bromo-2,2-dimethylquinolin-1-yl)-2,2,2-trifluoroethanone Structure

1-(6-bromo-2,2-...

N/A Structure

Trifluoroacetic anhydride Structure

Trifluoroacetic...

~86%

2,2,2-trifluoro-1-(6-hydroxy-2,2-dimethylquinolin-1-yl)ethanone Structure

2,2,2-trifluoro...

N-(2,2-dimethyl-1,2-dihydro-6-quinolyl)acetamide Structure

N-(2,2-dimethyl...

Trifluoroacetic anhydride Structure

Trifluoroacetic...

~49%

N-[2,2-dimethyl-1-(2,2,2-trifluoroacetyl)quinolin-6-yl]acetamide Structure

N-[2,2-dimethyl...

ethyl 4-(1,1-dimethyl-2-propynylamino)phenylacetate Structure

ethyl 4-(1,1-di...

~55%

ethyl 2-(2,2-dimethyl-1H-quinolin-6-yl)acetate Structure

ethyl 2-(2,2-di...

2,2-Dimethyl-1,2-dihydro-quinoline Structure

2,2-Dimethyl-1,...

Trifluoroacetic anhydride Structure

Trifluoroacetic...

~67%

1-(2,2-dimethylquinolin-1-yl)-2,2,2-trifluoroethanone Structure

1-(2,2-dimethyl...

N/A Structure

Trifluoroacetic anhydride Structure

Trifluoroacetic...

~%

1-(2,2-dimethylquinolin-1-yl)-2,2,2-trifluoroethanone Structure

1-(2,2-dimethyl...

6-iodo-2,2-dimethyl-1,2-dihydroquinoline Structure

6-iodo-2,2-dime...

Trifluoroacetic anhydride Structure

Trifluoroacetic...

~74%

2,2,2-trifluoro-1-(6-iodo-2,2-dimethylquinolin-1-yl)ethanone Structure

2,2,2-trifluoro...

3,4-epoxy-1-trifluoroacetyl-2,2,6-trimethyl-1,2,3,4-tetrahydroquinoline Structure

3,4-epoxy-1-tri...

~69%

2,2,2-trifluoro-1-(3-hydroxy-2,2,6-trimethyl-3,4-dihydroquinolin-1-yl)ethanone Structure

2,2,2-trifluoro...

2,2,6-trimethyl-1,2-dihydroquinoline Structure

2,2,6-trimethyl...

~%

2,2,2-trifluoro-1-(3-hydroxy-2,2,6-trimethyl-3,4-dihydroquinolin-1-yl)ethanone Structure

2,2,2-trifluoro...

N-(1,1-Dimethyl-2-propynyl)-p-toluidine Structure

N-(1,1-Dimethyl...

~%

2,2,2-trifluoro-1-(3-hydroxy-2,2,6-trimethyl-3,4-dihydroquinolin-1-yl)ethanone Structure

2,2,2-trifluoro...

2,2,2-trifluoro-1-(2,2,6-trimethylquinolin-1-yl)ethanone Structure

2,2,2-trifluoro...

~%

2,2,2-trifluoro-1-(3-hydroxy-2,2,6-trimethyl-3,4-dihydroquinolin-1-yl)ethanone Structure

2,2,2-trifluoro...