2-Benzazepines. 9. Synthesis and chemistry of 3H-2-benzazepine and pyrimido [4, 5-d][2] benzazepine derivatives

EJ Trybulski, RI Fryer, E Reeder, S Vitone…

Index: Trybulski, E.J.; Fryer, R.I.; Reeder, E.; Vitone, S.; Todaro, L. Journal of Organic Chemistry, 1986 , vol. 51, # 12 p. 2191 - 2202

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Citation Number: 14

Abstract

The synthesis of 8-chloro-l-phenyl-3H-2-benzazepine analogues 6a-c and their dihydro derivatives 9a-c from the corresponding alkynes la-c is discussed. The bromination followed by dehydrobromination of 6a-c led to the formation of the corresponding 5-bromo-l-phenyl- 3H-2-benzazepines 14a-c which were useful synthetic intermediates in the synthesis of more complex 2-benzazepine derivatives. An example of the utility for the vinyl bromides ...

 Related Synthetic Route
8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine hydrobromide Structure

101713-12-6

8-chloro-1-(2-c...

~86%

8-chloro-1-(2-chlorophenyl)-2-oxido-3H-2-benzazepin-2-ium Structure

81078-25-3

8-chloro-1-(2-c...

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N/A Structure

101713-13-7

N/A

~%

5-bromo-8-chloro-1-(2-fluorophenyl)-3H-2-benzazepine Structure

737712-15-1

5-bromo-8-chlor...

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8-chloro-1-(2-fluorophenyl)-4,5-dibromo-4,5-dihydro-3H-2-benzazepine Structure

101713-23-9

8-chloro-1-(2-f...

~0%

N/A Structure

101713-27-3

N/A

8-chloro-1-(2-fluorophenyl)-3H-2-benzazepine Structure

89376-31-8

8-chloro-1-(2-f...

5-bromo-8-chloro-1-(2-fluorophenyl)-3H-2-benzazepine Structure

737712-15-1

5-bromo-8-chlor...

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Methanol Structure

67-56-1

Methanol

8-chloro-1-(2-fluorophenyl)-4,5-dibromo-4,5-dihydro-3H-2-benzazepine Structure

101713-23-9

8-chloro-1-(2-f...

~%

5-bromo-8-chloro-1-(2-fluorophenyl)-3H-2-benzazepine Structure

737712-15-1

5-bromo-8-chlor...

8-chloro-1-(2-fluorophenyl)-3-methoxy-3H-2-benzazepine Structure

101713-25-1

8-chloro-1-(2-f...

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8-chloro-1-(2-fluorophenyl)-4,5-dibromo-4,5-dihydro-3H-2-benzazepine Structure

101713-23-9

8-chloro-1-(2-f...

tert-Butanol Structure

75-65-0

tert-Butanol

~0%

N/A Structure

101713-27-3

N/A

8-chloro-1-(2-fluorophenyl)-3H-2-benzazepine Structure

89376-31-8

8-chloro-1-(2-f...

Detail Learn More
8-chloro-1-phenyl-3H-2-benzazepine hydrobromide Structure

101713-14-8

8-chloro-1-phen...

~%

4,5-dibromo-8-chloro-1-phenyl-4,5-dihydro-3H-2-benzazepine Structure

81078-28-6

4,5-dibromo-8-c...

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4,5-dibromo-8-chloro-1-phenyl-4,5-dihydro-3H-2-benzazepine Structure

81078-28-6

4,5-dibromo-8-c...

~86%

5-bromo-8-chloro-1-phenyl-3H-2-benzazepine,hydrochloride Structure

81078-32-2

5-bromo-8-chlor...

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8-chloro-1-phenyl-3H-2-benzazepine hydrobromide Structure

101713-14-8

8-chloro-1-phen...

~%

5-bromo-8-chloro-1-phenyl-3H-2-benzazepine,hydrochloride Structure

81078-32-2

5-bromo-8-chlor...

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[2-(3-aminoprop-1-ynyl)-5-chlorophenyl]-(2-fluorophenyl)methanone Structure

76049-63-3

[2-(3-aminoprop...

~%

8-chloro-1-(2-fluorophenyl)-3H-2-benzazepine Structure

89376-31-8

8-chloro-1-(2-f...

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N/A Structure

101713-13-7

N/A

~%

8-chloro-1-(2-fluorophenyl)-3H-2-benzazepine Structure

89376-31-8

8-chloro-1-(2-f...

Learn More
8-chloro-1-(2-fluorophenyl)-4,5-dibromo-4,5-dihydro-3H-2-benzazepine Structure

101713-23-9

8-chloro-1-(2-f...

~0%

N/A Structure

101713-27-3

N/A

8-chloro-1-(2-fluorophenyl)-3H-2-benzazepine Structure

89376-31-8

8-chloro-1-(2-f...

5-bromo-8-chloro-1-(2-fluorophenyl)-3H-2-benzazepine Structure

737712-15-1

5-bromo-8-chlor...

Learn More
8-chloro-1-(2-fluorophenyl)-4,5-dibromo-4,5-dihydro-3H-2-benzazepine Structure

101713-23-9

8-chloro-1-(2-f...

tert-Butanol Structure

75-65-0

tert-Butanol

~0%

N/A Structure

101713-27-3

N/A

8-chloro-1-(2-fluorophenyl)-3H-2-benzazepine Structure

89376-31-8

8-chloro-1-(2-f...

Detail Learn More
8-chloro-1-phenyl-3H-2-benzazepine hydrobromide Structure

101713-14-8

8-chloro-1-phen...

~92%

8-Chloro-1-phenyl-3H-2-benzazepine 2-oxide Structure

81078-23-1

8-Chloro-1-phen...

Learn More
N/A Structure

101713-22-8

N/A

tert-Butanol Structure

75-65-0

tert-Butanol

~46%

5-bromo-8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine Structure

81078-36-6

5-bromo-8-chlor...

8-chloro-1-(2-chlorophenyl)-3-(1,1,-dimethylethoxy)-3H-2-benzazepine Structure

101713-24-0

8-chloro-1-(2-c...

Detail Learn More
Methanol Structure

67-56-1

Methanol

N/A Structure

101713-22-8

N/A

~21%

5-bromo-8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine Structure

81078-36-6

5-bromo-8-chlor...

8-chloro-1-(2-chlorophenyl)-3-methoxy-3H-2-benzazepine Structure

81078-37-7

8-chloro-1-(2-c...

Learn More
8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine hydrobromide Structure

101713-12-6

8-chloro-1-(2-c...

~%

5-bromo-8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine Structure

81078-36-6

5-bromo-8-chlor...

Learn More
N/A Structure

101713-22-8

N/A

~46%

5-bromo-8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine Structure

81078-36-6

5-bromo-8-chlor...

8-chloro-1-(2-chlorophenyl)-3-(1,1,-dimethylethoxy)-3H-2-benzazepine Structure

101713-24-0

8-chloro-1-(2-c...

8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine Structure

81078-18-4

8-chloro-1-(2-c...

Learn More
Methanol Structure

67-56-1

Methanol

N/A Structure

101713-22-8

N/A

~65%

5-bromo-8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine Structure

81078-36-6

5-bromo-8-chlor...

8-chloro-1-(2-chlorophenyl)-3-methoxy-3H-2-benzazepine Structure

81078-37-7

8-chloro-1-(2-c...

Learn More
8-chloro-1-(2-chlorophenyl)-5H-2-benzazepin-5-one Structure

101713-42-2

8-chloro-1-(2-c...

~%

8-chloro-1-(2-chlorophenyl)-3-methoxy-3H-2-benzazepine Structure

81078-37-7

8-chloro-1-(2-c...

Learn More
8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine hydrobromide Structure

101713-12-6

8-chloro-1-(2-c...

~%

8-chloro-1-(2-chlorophenyl)-3-methoxy-3H-2-benzazepine Structure

81078-37-7

8-chloro-1-(2-c...

Learn More
N/A Structure

101713-47-7

N/A

~%

8-chloro-1-(2-chlorophenyl)-3-methoxy-3H-2-benzazepine Structure

81078-37-7

8-chloro-1-(2-c...

Learn More
N/A Structure

101713-41-1

N/A

~%

8-chloro-1-(2-chlorophenyl)-3-methoxy-3H-2-benzazepine Structure

81078-37-7

8-chloro-1-(2-c...

Learn More
8-chloro-1-(2-chlorophenyl)-5H-2-benzazepin-5-ol Structure

101713-43-3

8-chloro-1-(2-c...

~%

8-chloro-1-(2-chlorophenyl)-3-methoxy-3H-2-benzazepine Structure

81078-37-7

8-chloro-1-(2-c...

Learn More
4,5-dibromo-8-chloro-1-phenyl-4,5-dihydro-3H-2-benzazepine Structure

81078-28-6

4,5-dibromo-8-c...

~85%

5-bromo-8-chloro-1-phenyl-3H-2-benzazepine Structure

89376-32-9

5-bromo-8-chlor...

Learn More
8-chloro-1-phenyl-3H-2-benzazepine hydrobromide Structure

101713-14-8

8-chloro-1-phen...

~%

5-bromo-8-chloro-1-phenyl-3H-2-benzazepine Structure

89376-32-9

5-bromo-8-chlor...

Learn More
Methanol Structure

67-56-1

Methanol

4,5-dibromo-8-chloro-1-phenyl-4,5-dihydro-3H-2-benzazepine Structure

81078-28-6

4,5-dibromo-8-c...

~%

5-bromo-8-chloro-1-phenyl-3H-2-benzazepine Structure

89376-32-9

5-bromo-8-chlor...

8-chloro-3-methoxy-1-phenyl-3H-2-benzazepine Structure

81078-33-3

8-chloro-3-meth...

Learn More
[2-(3-aminoprop-1-ynyl)-5-chlorophenyl]-(2-chlorophenyl)methanone Structure

76049-64-4

[2-(3-aminoprop...

~%

8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine Structure

81078-18-4

8-chloro-1-(2-c...

Learn More
N/A Structure

101713-22-8

N/A

tert-Butanol Structure

75-65-0

tert-Butanol

~2%

5-bromo-8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine Structure

81078-36-6

5-bromo-8-chlor...

8-chloro-1-(2-chlorophenyl)-3-(1,1,-dimethylethoxy)-3H-2-benzazepine Structure

101713-24-0

8-chloro-1-(2-c...

Detail Learn More
8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine hydrobromide Structure

101713-12-6

8-chloro-1-(2-c...

~%

8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine Structure

81078-18-4

8-chloro-1-(2-c...

Learn More
N/A Structure

101713-22-8

N/A

~3%

5-bromo-8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine Structure

81078-36-6

5-bromo-8-chlor...

8-chloro-1-(2-chlorophenyl)-3-(1,1,-dimethylethoxy)-3H-2-benzazepine Structure

101713-24-0

8-chloro-1-(2-c...

8-chloro-1-(2-chlorophenyl)-3H-2-benzazepine Structure

81078-18-4

8-chloro-1-(2-c...

Learn More
carbon monoxide Structure

201230-82-2

carbon monoxide

5-bromo-8-chloro-1-phenyl-3H-2-benzazepine,hydrochloride Structure

81078-32-2

5-bromo-8-chlor...

Butanol Structure

71-36-3

Butanol

~13%

butyl 8-chloro-1-phenyl-3H-2-benzazepine-5-carboxylate Structure

81993-61-5

butyl 8-chloro-...

Detail Learn More
4,5-dibromo-8-chloro-1-phenyl-4,5-dihydro-3H-2-benzazepine Structure

81078-28-6

4,5-dibromo-8-c...

~%

butyl 8-chloro-1-phenyl-5H-2-benzazepine-5-carboxylate Structure

81993-60-4

butyl 8-chloro-...

Learn More
8-chloro-1-phenyl-3H-2-benzazepine hydrobromide Structure

101713-14-8

8-chloro-1-phen...

~%

butyl 8-chloro-1-phenyl-5H-2-benzazepine-5-carboxylate Structure

81993-60-4

butyl 8-chloro-...

Learn More
carbon monoxide Structure

201230-82-2

carbon monoxide

5-bromo-8-chloro-1-phenyl-3H-2-benzazepine,hydrochloride Structure

81078-32-2

5-bromo-8-chlor...

Butanol Structure

71-36-3

Butanol

~29%

butyl 8-chloro-1-phenyl-3H-2-benzazepine-5-carboxylate Structure

81993-61-5

butyl 8-chloro-...

Detail Learn More
4,5-dibromo-8-chloro-1-phenyl-4,5-dihydro-3H-2-benzazepine Structure

81078-28-6

4,5-dibromo-8-c...

~%

butyl 8-chloro-1-phenyl-3H-2-benzazepine-5-carboxylate Structure

81993-61-5

butyl 8-chloro-...

Learn More
8-chloro-1-phenyl-3H-2-benzazepine hydrobromide Structure

101713-14-8

8-chloro-1-phen...

~%

butyl 8-chloro-1-phenyl-3H-2-benzazepine-5-carboxylate Structure

81993-61-5

butyl 8-chloro-...

Learn More
[2-(3-aminoprop-1-ynyl)-5-chlorophenyl]-phenylmethanone Structure

76049-61-1

[2-(3-aminoprop...

~%

8-chloro-1-phenyl-3H-2-benzazepine Structure

81078-22-0

8-chloro-1-phen...

Learn More
N/A Structure

101713-13-7

N/A

~92%

8-chloro-1-(2-fluorophenyl)-2-oxido-3H-2-benzazepin-2-ium Structure

81078-24-2

8-chloro-1-(2-f...

Learn More

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