Synthetic uses of open-chain analogs of Reissert compounds

…, AV Grossi, RJ MacDonald, AP Stamegna

Index: McEwen, William E.; Grossi, Anthony V.; MacDonald, Russell J.; Stamegna, Andrew P. Journal of Organic Chemistry, 1980 , vol. 45, # 7 p. 1301 - 1308

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Citation Number: 44

Abstract

Open-chain analogues, 2, of Reissert compounds are readily obtained by reaction of cyanohydrins with primary amines, the resulting aminonitriles, 1, then behg acylated. Hydrofluoroborate salts, 3, of 2 are prepared by reaction with fluoroboric acid in glacial acetic acid. The salts, 3, undergo 1, 3-dipolar addition reactions with reactive alkynes to give substituted pyrroles and with ethyl acrylate to give a different type of substituted pyrrole, ...

 Related Synthetic Route
N-(1-cyano-1-(3-methoxyphenyl)-2-phenylethyl)-N-phenylbenzamide Structure

72867-67-5

N-(1-cyano-1-(3...

~62%

3'-METHOXY-2-PHENYLACETOPHENONE Structure

62381-24-2

3'-METHOXY-2-PH...

2-(3-methyloxyphenyl)-2-(phenylamino)acetonitrile Structure

72867-30-2

2-(3-methyloxyp...

~%

3'-METHOXY-2-PHENYLACETOPHENONE Structure

62381-24-2

3'-METHOXY-2-PH...

Benzyl bromide Structure

100-39-0

Benzyl bromide

~%

3'-METHOXY-2-PHENYLACETOPHENONE Structure

62381-24-2

3'-METHOXY-2-PH...

N-(cyano(3-methoxyphenyl)methyl)-N-phenylbenzamide Structure

72867-41-5

N-(cyano(3-meth...

~%

3'-METHOXY-2-PHENYLACETOPHENONE Structure

62381-24-2

3'-METHOXY-2-PH...

N-(1-cyano-1-(2-methoxyphenyl)-2-phenylethyl)-N-phenylbenzamide Structure

72867-68-6

N-(1-cyano-1-(2...

~94%

Ethanone,1-(2-methoxyphenyl)-2-phenyl- Structure

33470-10-9

Ethanone,1-(2-m...

2-methoxy-α-(phenylamino)-benzeneacetonitrile Structure

72867-31-3

2-methoxy-α-(ph...

~%

Ethanone,1-(2-methoxyphenyl)-2-phenyl- Structure

33470-10-9

Ethanone,1-(2-m...

o-Anisaldehyde Structure

135-02-4

o-Anisaldehyde

~%

Ethanone,1-(2-methoxyphenyl)-2-phenyl- Structure

33470-10-9

Ethanone,1-(2-m...

N-(cyano(2-methoxyphenyl)methyl)-N-phenylbenzamide Structure

72867-42-6

N-(cyano(2-meth...

~%

Ethanone,1-(2-methoxyphenyl)-2-phenyl- Structure

33470-10-9

Ethanone,1-(2-m...

N-(1-cyano-1,2-diphenylethyl)-N-phenylbenzamide Structure

72867-62-0

N-(1-cyano-1,2-...

~65%

2-Phenylacetophenone Structure

451-40-1

2-Phenylacetophenone

N-(1-(4-chlorophenyl)-1-cyano-2-phenylethyl)-N-phenylbenzamide Structure

72867-63-1

N-(1-(4-chlorop...

~97%

Benzyl 4-chlorophenyl ketone Structure

1889-71-0

Benzyl 4-chloro...

Formaldehyde Structure

50-00-0

Formaldehyde

Benzylamine Structure

100-46-9

Benzylamine

~%

2-(benzylamino)acetonitrile Structure

3010-05-7

2-(benzylamino)...

Benzyl bromide Structure

100-39-0

Benzyl bromide

~%

Ethanone,1-(2-methoxyphenyl)-2-phenyl- Structure

33470-10-9

Ethanone,1-(2-m...

5-imino-2,3,4-triphenyl-1,3-oxazolinium fluoroborate Structure

72867-52-8

5-imino-2,3,4-t...

methylpropiolate Structure

922-67-8

methylpropiolate

~68%

1H-Pyrrole-3-carboxylicacid, 1,2,5-triphenyl-, methyl ester Structure

30082-52-1

1H-Pyrrole-3-ca...

N-[cyano(phenyl)methyl]-N-phenylbenzamide Structure

14062-91-0

N-[cyano(phenyl...

acrylic acid methyl ester Structure

292638-85-8

acrylic acid me...

~47%

1H-Pyrrole-3-carboxylicacid, 1,2,5-triphenyl-, methyl ester Structure

30082-52-1

1H-Pyrrole-3-ca...

Benzeneacetonitrile, a-(phenylamino)- Structure

4553-59-7

Benzeneacetonit...

~%

1H-Pyrrole-3-carboxylicacid, 1,2,5-triphenyl-, methyl ester Structure

30082-52-1

1H-Pyrrole-3-ca...

Benzoyl chloride Structure

98-88-4

Benzoyl chloride

~%

1H-Pyrrole-3-carboxylicacid, 1,2,5-triphenyl-, methyl ester Structure

30082-52-1

1H-Pyrrole-3-ca...

Benzaldehyde Structure

100-52-7

Benzaldehyde

~%

1H-Pyrrole-3-carboxylicacid, 1,2,5-triphenyl-, methyl ester Structure

30082-52-1

1H-Pyrrole-3-ca...

Structure

74497-02-2

~%

1H-Pyrrole-3-carboxylicacid, 1,2,5-triphenyl-, methyl ester Structure

30082-52-1

1H-Pyrrole-3-ca...

N-[cyano(phenyl)methyl]-N-phenylbenzamide Structure

14062-91-0

N-[cyano(phenyl...

~%

1H-Pyrrole-3-carboxylicacid, 1,2,5-triphenyl-, methyl ester Structure

30082-52-1

1H-Pyrrole-3-ca...

N-(1-cyano-2-(naphthalen-1-yl)-1-phenylethyl)-N-phenylbenzamide Structure

72867-71-1

N-(1-cyano-2-(n...

~71%

2-naphthalen-1-yl-1-phenylethanone Structure

16216-08-3

2-naphthalen-1-...

N-[cyano(phenyl)methyl]-N-phenylbenzamide Structure

14062-91-0

N-[cyano(phenyl...

~%

2-naphthalen-1-yl-1-phenylethanone Structure

16216-08-3

2-naphthalen-1-...

Benzoyl chloride Structure

98-88-4

Benzoyl chloride

~%

2-naphthalen-1-yl-1-phenylethanone Structure

16216-08-3

2-naphthalen-1-...

N-(1-(3-chlorophenyl)-1-cyano-2-phenylethyl)-N-phenylbenzamide Structure

72867-64-2

N-(1-(3-chlorop...

~90%

Ethanone,1-(3-chlorophenyl)-2-phenyl- Structure

62482-45-5

Ethanone,1-(3-c...

3-Chlorobenzaldehyde Structure

587-04-2

3-Chlorobenzaldehyde

~%

Ethanone,1-(3-chlorophenyl)-2-phenyl- Structure

62482-45-5

Ethanone,1-(3-c...

Benzyl bromide Structure

100-39-0

Benzyl bromide

~%

Ethanone,1-(3-chlorophenyl)-2-phenyl- Structure

62482-45-5

Ethanone,1-(3-c...

N-((3-chlorophenyl)(cyano)methyl)-N-phenylbenzamide Structure

72867-38-0

N-((3-chlorophe...

~%

Ethanone,1-(3-chlorophenyl)-2-phenyl- Structure

62482-45-5

Ethanone,1-(3-c...

N-(1-cyano-1-(3,4-dimethoxyphenyl)-2-phenylethyl)-N-phenylbenzamide Structure

72867-66-4

N-(1-cyano-1-(3...

~73%

1-(3,4-Dimethoxyphenyl)-2-phenylethanone Structure

3141-93-3

1-(3,4-Dimethox...

Benzaldehyde Structure

100-52-7

Benzaldehyde

Structure

74497-02-2

~%

Benzeneacetonitrile, a-(phenylamino)- Structure

4553-59-7

Benzeneacetonit...

N-(1-(2-chlorophenyl)-1-cyano-2-phenylethyl)-N-phenylbenzamide Structure

72867-65-3

N-(1-(2-chlorop...

~33%

1-(2-chlorophenyl)-2-phenylethanone Structure

72867-72-2

1-(2-chlorophen...

2-(N-anilino)-2-(3-chlorophenyl)acetonitrile Structure

72867-29-9

2-(N-anilino)-2...

~%

Ethanone,1-(3-chlorophenyl)-2-phenyl- Structure

62482-45-5

Ethanone,1-(3-c...

Benzeneacetonitrile, a-(phenylamino)- Structure

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Benzeneacetonit...

~%

2-anilino-1,2-diphenyl-ethanone Structure

5722-91-8

2-anilino-1,2-d...

Benzoyl chloride Structure

98-88-4

Benzoyl chloride

~%

2-anilino-1,2-diphenyl-ethanone Structure

5722-91-8

2-anilino-1,2-d...

Structure

74497-02-2

~%

2-anilino-1,2-diphenyl-ethanone Structure

5722-91-8

2-anilino-1,2-d...

N-[cyano(phenyl)methyl]-N-phenylbenzamide Structure

14062-91-0

N-[cyano(phenyl...

Benzaldehyde Structure

100-52-7

Benzaldehyde

~%

2-anilino-1,2-diphenyl-ethanone Structure

5722-91-8

2-anilino-1,2-d...

Benzaldehyde Structure

100-52-7

Benzaldehyde

4-Chloroaniline Structure

106-47-8

4-Chloroaniline

~%

2-(4-chloroanilino)-2-phenylacetonitrile Structure

4686-05-9

2-(4-chloroanil...

4-Chlorobenzaldehyde Structure

104-88-1

4-Chlorobenzaldehyde

Structure

74497-02-2

~%

2-anilino-2-(4-chlorophenyl)acetonitrile Structure

32377-36-9

2-anilino-2-(4-...

Benzaldehyde Structure

100-52-7

Benzaldehyde

~%

N-[cyano(phenyl)methyl]-N-phenylbenzamide Structure

14062-91-0

N-[cyano(phenyl...

Structure

74497-02-2

~%

N-[cyano(phenyl)methyl]-N-phenylbenzamide Structure

14062-91-0

N-[cyano(phenyl...


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