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

Electrophilic aromatic substitution with N-methoxy-N-acylnitrenium ions generated from N-chloro-N-methoxy amides: syntheses of nitrogen heterocyclic compounds …

M Kawase, T Kitamura, Y Kikugawa

Index: Kawase, Masami; Kitamura, Takahiro; Kikugawa, Yasuo Journal of Organic Chemistry, 1989 , vol. 54, # 14 p. 3394 - 3403

Full Text: HTML

Citation Number: 117

Abstract

N-Methoxy-N-acylnitrenium ions (11), generated by treatment of N-chloro-N-methoxyamides with silver carbonate in trifluoroacetic acid, react with arenes to give N-aryl-N- methoxyamides in good yields. In the case of the intramolecular cyclization of N-chloro-N- methoxy-2-phenylacetamides, the mode of cyclization is highly dependent on the nature of ortho or para substituent groups. Nitrenium ions I1 can primarily attack three positions (C- ...

1,5,6-trimethoxyindolin-2-one Structure

1,5,6-trimethox...

~90%

5,6-dimethoxy-1,3-dihydroindol-2-one Structure

5,6-dimethoxy-1...

3,4-Dimethoxyphenylacetic acid Structure

3,4-Dimethoxyph...

~%

5,6-dimethoxy-1,3-dihydroindol-2-one Structure

5,6-dimethoxy-1...

2-(3,4-dimethoxyphenyl)-N-methoxyacetamide Structure

2-(3,4-dimethox...

~%

5,6-dimethoxy-1,3-dihydroindol-2-one Structure

5,6-dimethoxy-1...

O-Methoxyamine HCl Structure

O-Methoxyamine HCl

3-Phenylpropanoyl chloride Structure

3-Phenylpropano...

~92%

N-methoxy-3-phenylpropanamide Structure

N-methoxy-3-phe...

1-methoxy-6-methylindolin-2-one Structure

1-methoxy-6-met...

~88%

6-Methylindolin-2-one Structure

6-Methylindolin...

N-chloro-N-methoxy-2-(2-nitrophenyl)acetamide Structure

N-chloro-N-meth...

~54%

(2-Nitrophenyl)acetic acid Structure

(2-Nitrophenyl)...

1-methoxy-4-nitroindolin-2-one Structure

1-methoxy-4-nit...

Benzeneacetyl chloride,2-nitro- Structure

Benzeneacetyl c...

~%

(2-Nitrophenyl)acetic acid Structure

(2-Nitrophenyl)...

N-methoxy-2-(2-nitrophenyl)acetamide Structure

N-methoxy-2-(2-...

~%

(2-Nitrophenyl)acetic acid Structure

(2-Nitrophenyl)...

N-methoxybenzamide Structure

N-methoxybenzamide

~90%

N-chloro-N-methoxybenzamide Structure

N-chloro-N-meth...

N/A Structure

~96%

6-Methoxyoxindole Structure

6-Methoxyoxindole

O-Methoxyamine HCl Structure

O-Methoxyamine HCl

Phenylacetyl chloride Structure

Phenylacetyl ch...

~95%

N-methoxy-2-phenylacetamide Structure

N-methoxy-2-phe...

1,5-dimethoxyindolin-2-one Structure

1,5-dimethoxyin...

~78%

5-Methoxyoxindole Structure

5-Methoxyoxindole

1-methoxy-4-methylindolin-2-one Structure

1-methoxy-4-met...

~94%

4-Methylindolin-2-one Structure

4-Methylindolin...

1,3-dihydro-1-methoxy-2H-benz[c]indol-2-one Structure

1,3-dihydro-1-m...

~85%

1,3-dihydrobenzo[e]indol-2-one Structure

1,3-dihydrobenz...

1-Naphthylacetyl chloride Structure

1-Naphthylacety...

~%

1,3-dihydrobenzo[e]indol-2-one Structure

1,3-dihydrobenz...

2-Naphthylacetyl chloride Structure

2-Naphthylacety...

~%

1,3-dihydrobenzo[e]indol-2-one Structure

1,3-dihydrobenz...

N-methoxy-2-(1-naphthyl)acetamide Structure

N-methoxy-2-(1-...

~%

1,3-dihydrobenzo[e]indol-2-one Structure

1,3-dihydrobenz...

N-chloro-N-methoxy-2-(1-naphthyl)acetamide Structure

N-chloro-N-meth...

~%

1,3-dihydrobenzo[e]indol-2-one Structure

1,3-dihydrobenz...

N-chloro-N-methoxy-2-(2-naphthyl)acetamide Structure

N-chloro-N-meth...

~%

1,3-dihydrobenzo[e]indol-2-one Structure

1,3-dihydrobenz...

4-chloro-1-methoxyindolin-2-one Structure

4-chloro-1-meth...

~40%

4-Chloroindole Structure

2-(2-bromophenyl)-N-methoxyacetamide Structure

2-(2-bromopheny...

~94%

2-(2-bromophenyl)-N-chloro-N-methoxyacetamide Structure

2-(2-bromopheny...

(2-Bromophenyl)acetyl chloride Structure

(2-Bromophenyl)...

~%

2-(2-bromophenyl)-N-chloro-N-methoxyacetamide Structure

2-(2-bromopheny...