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- ...

 Related Synthetic Route
2,2,6-trimethyl-1,2-dihydroquinoline Structure

14465-54-4

2,2,6-trimethyl...

Trifluoroacetic anhydride Structure

407-25-0

Trifluoroacetic...

~72%

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

828938-83-6

2,2,2-trifluoro...

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

14465-52-2

N-(1,1-Dimethyl...

~%

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

828938-83-6

2,2,2-trifluoro...

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

41549-16-0

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

Trifluoroacetic anhydride Structure

407-25-0

Trifluoroacetic...

~42%

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

828938-84-7

2,2,2-trifluoro...

Learn More
N/A Structure

14465-44-2

N/A

~%

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

828938-84-7

2,2,2-trifluoro...

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

171898-86-5

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

~14%

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

828939-18-0

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

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

14465-54-4

2,2,6-trimethyl...

~%

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

828939-18-0

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

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

14465-52-2

N-(1,1-Dimethyl...

~%

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

828939-18-0

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

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

14465-54-4

2,2,6-trimethyl...

~%

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

828939-20-4

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

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

14465-52-2

N-(1,1-Dimethyl...

~%

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

828939-20-4

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

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

171898-86-5

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

~%

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

828939-20-4

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

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

137434-04-9

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

Trifluoroacetic anhydride Structure

407-25-0

Trifluoroacetic...

~88%

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

828938-85-8

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

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

142559-77-1

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

~%

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

828938-85-8

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

Learn More
N/A Structure

171898-77-4

N/A

Trifluoroacetic anhydride Structure

407-25-0

Trifluoroacetic...

~86%

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

828938-86-9

2,2,2-trifluoro...

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

171898-78-5

N-(2,2-dimethyl...

Trifluoroacetic anhydride Structure

407-25-0

Trifluoroacetic...

~49%

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

828938-87-0

N-[2,2-dimethyl...

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

87547-10-2

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

~55%

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

87547-15-7

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

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

14465-61-3

2,2-Dimethyl-1,...

Trifluoroacetic anhydride Structure

407-25-0

Trifluoroacetic...

~67%

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

828938-88-1

1-(2,2-dimethyl...

Learn More
N/A Structure

171898-79-6

N/A

Trifluoroacetic anhydride Structure

407-25-0

Trifluoroacetic...

~%

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

828938-88-1

1-(2,2-dimethyl...

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

171898-80-9

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

Trifluoroacetic anhydride Structure

407-25-0

Trifluoroacetic...

~74%

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

828938-90-5

2,2,2-trifluoro...

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

828939-12-4

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

~69%

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

828939-13-5

2,2,2-trifluoro...

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

14465-54-4

2,2,6-trimethyl...

~%

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

828939-13-5

2,2,2-trifluoro...

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

14465-52-2

N-(1,1-Dimethyl...

~%

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

828939-13-5

2,2,2-trifluoro...

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

828938-83-6

2,2,2-trifluoro...

~%

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

828939-13-5

2,2,2-trifluoro...

Learn More

Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer

Copyright © 2026 ChemSrc All Rights Reserved