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

2-Benzazepines. 8. Zerovalent nickel mediated biaryl synthesis of an anxiolytic pyrimido [5, 4-d][2] benzazepine

…, B Schaer, FT Bizzarro, JB Cheung

Index: Coffen; Schaer; Bizzarro; Cheung Journal of Organic Chemistry, 1984 , vol. 49, # 2 p. 296 - 300

Full Text: HTML

Citation Number: 21

Abstract

9-Chloro-7-(2-chlorophenyl) pyrimido [5, 4-d][2] benzazepine, a potent anxiolytic agent, was synthesized in three steps from 4-chloro-5-methylpyrimidine and 2-iodo-2', 5- dichlorobenzophenon~ In the key step these materials were coupled in an unsymmetrical biaryl synthesis mediated with zerovalent nickel. The methyl group of the resulting product was brominated with NBS, and the seven-membered ring was closed with ammonia. ...

N-[(5-chloro-2-iodophenyl)-(2-chlorophenyl)methylidene]hydroxylamine Structure

N-[(5-chloro-2-...

~93%

5-Chloro-3-(2-chlorophenyl)benzo[d]isoxazole Structure

5-Chloro-3-(2-c...

2-Amino-2',5-dichlorobenzophenone Structure

2-Amino-2',5-di...

~%

5-Chloro-3-(2-chlorophenyl)benzo[d]isoxazole Structure

5-Chloro-3-(2-c...

(5-chloro-2-iodophenyl)-(2-chlorophenyl)methanone Structure

(5-chloro-2-iod...

~%

5-Chloro-3-(2-chlorophenyl)benzo[d]isoxazole Structure

5-Chloro-3-(2-c...

3,3-Diethoxy-2-methylpropanoic acid ethyl ester Structure

3,3-Diethoxy-2-...

thiourea Structure

~48%

thiothymine Structure

2-Amino-2',5-dichlorobenzophenone Structure

2-Amino-2',5-di...

~%

(2-CHLOROPHENYL)(3-CHLOROPHENYL)METHANONE Structure

(2-CHLOROPHENYL...

(5-chloro-2-iodophenyl)-(2-chlorophenyl)methanone Structure

(5-chloro-2-iod...

2-amino-2',5-dichlorobenzophenone oxime Structure

2-amino-2',5-di...

~83%

6-chloro-4-(2-chlorophenyl)-3-oxido-1,2,3-benzotriazin-3-ium Structure

6-chloro-4-(2-c...

2-Amino-2',5-dichlorobenzophenone Structure

2-Amino-2',5-di...

~%

6-chloro-4-(2-chlorophenyl)-3-oxido-1,2,3-benzotriazin-3-ium Structure

6-chloro-4-(2-c...

(5-chloro-2-iodophenyl)-(2-chlorophenyl)methanone Structure

(5-chloro-2-iod...

~%

6-chloro-4-(2-chlorophenyl)-3-oxido-1,2,3-benzotriazin-3-ium Structure

6-chloro-4-(2-c...

2-Amino-2',5-dichlorobenzophenone Structure

2-Amino-2',5-di...

~%

(2-CHLOROPHENYL)(3-CHLOROPHENYL)METHANONE Structure

(2-CHLOROPHENYL...

(5-chloro-2-iodophenyl)-(2-chlorophenyl)methanone Structure

(5-chloro-2-iod...

2',5-Dichloro-2-(5-(bromomethyl)-4-pyrimidinyl)benzophenone Structure

2',5-Dichloro-2...

~65%

Ro 22-3245 Structure

[5-chloro-2-(5-methylpyrimidin-4-yl)phenyl]-(2-chlorophenyl)methanone Structure

[5-chloro-2-(5-...

~%

Ro 22-3245 Structure

4-Chloro-5-methylpyrimidine Structure

4-Chloro-5-meth...

(5-chloro-2-iodophenyl)-(2-chlorophenyl)methanone Structure

(5-chloro-2-iod...

~13%

9H-Fluoren-9-one,2-chloro- Structure

9H-Fluoren-9-on...

5-methyl-4-(5-methylpyrimidin-4-yl)pyrimidine Structure

5-methyl-4-(5-m...

Detail

4-Chloro-5-methylpyrimidine Structure

4-Chloro-5-meth...

(5-chloro-2-iodophenyl)-(2-chlorophenyl)methanone Structure

(5-chloro-2-iod...

~27%

9H-Fluoren-9-one,2-chloro- Structure

9H-Fluoren-9-on...

5-methyl-4-(5-methylpyrimidin-4-yl)pyrimidine Structure

5-methyl-4-(5-m...

Detail

4-Chloro-5-methylpyrimidine Structure

4-Chloro-5-meth...

(5-chloro-2-iodophenyl)-(2-chlorophenyl)methanone Structure

(5-chloro-2-iod...

~16%

9H-Fluoren-9-one,2-chloro- Structure

9H-Fluoren-9-on...

5-methyl-4-(5-methylpyrimidin-4-yl)pyrimidine Structure

5-methyl-4-(5-m...

Detail

4-Chloro-5-pyrimidinecarbonitrile Structure

4-Chloro-5-pyri...

(5-chloro-2-iodophenyl)-(2-chlorophenyl)methanone Structure

(5-chloro-2-iod...

~8%

4-[4-chloro-2-(2-chlorobenzoyl)phenyl]pyrimidine-5-carbonitrile Structure

4-[4-chloro-2-(...

2-Amino-2',5-dichlorobenzophenone Structure

2-Amino-2',5-di...

~%

4-[4-chloro-2-(2-chlorobenzoyl)phenyl]pyrimidine-5-carbonitrile Structure

4-[4-chloro-2-(...

(5-chloro-2-iodophenyl)-(2-chlorophenyl)methanone Structure

(5-chloro-2-iod...

~7%

N-[(5-chloro-2-iodophenyl)-(2-chlorophenyl)methylidene]hydroxylamine Structure

N-[(5-chloro-2-...

2',5-Dichloro-2-iodobenzophenone (E)-Oxime Structure

2',5-Dichloro-2...

2-Amino-2',5-dichlorobenzophenone Structure

2-Amino-2',5-di...

~%

N-[(5-chloro-2-iodophenyl)-(2-chlorophenyl)methylidene]hydroxylamine Structure

N-[(5-chloro-2-...