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

Spiropiperidines. I. Synthesis of 1'-substituted spiro (4H-3, 1-benzoxazine-4, 4'-piperidin)-2 (1H)-one derivatives and evaluation of their antihypertensive activity.

高井春樹，小場瀬宏之，寺西正行，唐沢啓…

Index: Takai; Obase; Teranishi; Karasawa; Kubo; Shuto; Kasuya; Hashikami; Karashima; Shigenobu Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 3 p. 1129 - 1139

Full Text: HTML

Citation Number: 13

Abstract

... The eluent was worked up in the usual manner to give 3a (17.5 g, 29.1%) as the free base. ... Kubo, K. Shuto, and N. Nakamizo, Abstracts of Papers, the 102nd Annual Meeting of the Pharmaceutical Society of Japan, Osaka, April 1982, p. 383; b) H. Takai, H. Obase, N. Nakamizo ...

1'-benzyl-6-chlorospiro(4H-3,1-benzoxazine-4,4'-piperidin)-2(1H)-one Structure

1'-benzyl-6-chl...

~88%

Spiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one hydrochloride Structure

Spiro[benzo[d][...

N-Benzyl-4-piperidone Structure

N-Benzyl-4-pipe...

~%

Spiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one hydrochloride Structure

Spiro[benzo[d][...

4-Chloropivalanilide Structure

4-Chloropivalanilide

~%

Spiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one hydrochloride Structure

Spiro[benzo[d][...

1-benzyl-4-hydroxy-4-(2-pivaloylamino-5-chlorophenyl)piperidine Structure

1-benzyl-4-hydr...

~%

Spiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one hydrochloride Structure

Spiro[benzo[d][...

4-(2-amino-5-chlorophenyl)-1-benzylpiperidin-4-ol Structure

4-(2-amino-5-ch...

~%

Spiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one hydrochloride Structure

Spiro[benzo[d][...

1-benzyl-4-hydroxy-4-(2-amino-5-chlorophenyl)piperidine Structure

1-benzyl-4-hydr...

~%

Spiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one hydrochloride Structure

Spiro[benzo[d][...

1'-(2-oxo-2-phenylethyl)spiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one Structure

1'-(2-oxo-2-phe...

~95%

1'-(2-hydroxy-2-phenylethyl)spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-(2-hydroxy-2...

N-Benzyl-4-piperidone Structure

N-Benzyl-4-pipe...

~%

1'-(2-hydroxy-2-phenylethyl)spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-(2-hydroxy-2...

4-Chloropivalanilide Structure

4-Chloropivalanilide

~%

1'-(2-hydroxy-2-phenylethyl)spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-(2-hydroxy-2...

1-benzyl-4-hydroxy-4-(2-pivaloylamino-5-chlorophenyl)piperidine Structure

1-benzyl-4-hydr...

~%

1'-(2-hydroxy-2-phenylethyl)spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-(2-hydroxy-2...

4-(2-amino-5-chlorophenyl)-1-benzylpiperidin-4-ol Structure

4-(2-amino-5-ch...

~%

1'-(2-hydroxy-2-phenylethyl)spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-(2-hydroxy-2...

1-benzyl-4-hydroxy-4-(2-amino-5-chlorophenyl)piperidine Structure

1-benzyl-4-hydr...

~%

1'-(2-hydroxy-2-phenylethyl)spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-(2-hydroxy-2...

1'-benzyl-6-chlorospiro(4H-3,1-benzoxazine-4,4'-piperidin)-2(1H)-one Structure

1'-benzyl-6-chl...

~%

1'-(2-hydroxy-2-phenylethyl)spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-(2-hydroxy-2...

Spiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one hydrochloride Structure

Spiro[benzo[d][...

~%

1'-(2-hydroxy-2-phenylethyl)spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-(2-hydroxy-2...

1-benzyl-4-hydroxy-4-(2-pivaloylamino-5-chlorophenyl)piperidine Structure

1-benzyl-4-hydr...

~61%

4-(2-amino-5-chlorophenyl)-1-benzylpiperidin-4-ol Structure

4-(2-amino-5-ch...

N-Benzyl-4-piperidone Structure

N-Benzyl-4-pipe...

~%

4-(2-amino-5-chlorophenyl)-1-benzylpiperidin-4-ol Structure

4-(2-amino-5-ch...

4-Chloropivalanilide Structure

4-Chloropivalanilide

~%

4-(2-amino-5-chlorophenyl)-1-benzylpiperidin-4-ol Structure

4-(2-amino-5-ch...

N/A Structure

~94%

1'-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-[2-(3,4-dime...

N-Benzyl-4-piperidone Structure

N-Benzyl-4-pipe...

~%

1'-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-[2-(3,4-dime...

4-Chloropivalanilide Structure

4-Chloropivalanilide

~%

1'-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-[2-(3,4-dime...

1-benzyl-4-hydroxy-4-(2-pivaloylamino-5-chlorophenyl)piperidine Structure

1-benzyl-4-hydr...

~%

1'-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-[2-(3,4-dime...

4-(2-amino-5-chlorophenyl)-1-benzylpiperidin-4-ol Structure

4-(2-amino-5-ch...

~%

1'-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-[2-(3,4-dime...

1-benzyl-4-hydroxy-4-(2-amino-5-chlorophenyl)piperidine Structure

1-benzyl-4-hydr...

~%

1'-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-[2-(3,4-dime...

1'-benzyl-6-chlorospiro(4H-3,1-benzoxazine-4,4'-piperidin)-2(1H)-one Structure

1'-benzyl-6-chl...

~%

1'-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-[2-(3,4-dime...

Spiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one hydrochloride Structure

Spiro[benzo[d][...

~%

1'-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

1'-[2-(3,4-dime...

1'-(4-chlorobenzoylmethyl)-6-chlorospiro(4H-3,1-bezoxazine-4,4'-piperidin)-2(1H)-one Structure

1'-(4-chloroben...

~89%

6-chloro-1'-[2-(4-chlorophenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

6-chloro-1'-[2-...

N-Benzyl-4-piperidone Structure

N-Benzyl-4-pipe...

~%

6-chloro-1'-[2-(4-chlorophenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

6-chloro-1'-[2-...

4-Chloropivalanilide Structure

4-Chloropivalanilide

~%

6-chloro-1'-[2-(4-chlorophenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

6-chloro-1'-[2-...

1-benzyl-4-hydroxy-4-(2-pivaloylamino-5-chlorophenyl)piperidine Structure

1-benzyl-4-hydr...

~%

6-chloro-1'-[2-(4-chlorophenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

6-chloro-1'-[2-...

4-(2-amino-5-chlorophenyl)-1-benzylpiperidin-4-ol Structure

4-(2-amino-5-ch...

~%

6-chloro-1'-[2-(4-chlorophenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

6-chloro-1'-[2-...

1-benzyl-4-hydroxy-4-(2-amino-5-chlorophenyl)piperidine Structure

1-benzyl-4-hydr...

~%

6-chloro-1'-[2-(4-chlorophenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

6-chloro-1'-[2-...

1'-benzyl-6-chlorospiro(4H-3,1-benzoxazine-4,4'-piperidin)-2(1H)-one Structure

1'-benzyl-6-chl...

~%

6-chloro-1'-[2-(4-chlorophenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

6-chloro-1'-[2-...

vinyl 6-chloro-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-carboxylate Structure

vinyl 6-chloro-...

~%

6-chloro-1'-[2-(4-chlorophenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

6-chloro-1'-[2-...

2,2,2-trichloroethyl 6-chloro-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-carboxylate Structure

2,2,2-trichloro...

~%

6-chloro-1'-[2-(4-chlorophenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

6-chloro-1'-[2-...

6-chlorospiro(4H-3,1-benzoxazine-4,4'-piperidin)-2(1H)-one*HCl Structure

6-chlorospiro(4...

~%

6-chloro-1'-[2-(4-chlorophenyl)-2-hydroxyethyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Structure

6-chloro-1'-[2-...