Journal of heterocyclic chemistry

Synthesis of indole derivatives from N??alkenyl??o??chloroanilines with zero??valent nickel complex

JG Rodriguez, L Canoira

Index: Rodriguez, J. G.; Canoira, L. Journal of Heterocyclic Chemistry, 1985 , vol. 22, p. 883 - 888

Full Text: HTML

Citation Number: 12

Abstract

Abstract Reaction of N-alkenyl-o-chloroanilines in toluene with tetrakis (triphenylphosphine) nickel (0) was carried out mainly to give indole and indoline derivatives in good yields. A detailed analysis of the reaction products has been done and it allows us to confirm the postulated mechanism of the cyclization reaction. Torsional hindrance around the N [BOND] C [BOND] Csp 2 bond seems to prevent the cyclization reaction.

 Related Synthetic Route
N/A Structure

13519-87-4

N/A

~16%

1H-Indole,1,3-dimethyl- Structure

875-30-9

1H-Indole,1,3-d...

(2-Ethylphenyl)methylamine Structure

1821-38-1

(2-Ethylphenyl)...

2-CHLORO-N-METHYLANILINE Structure

932-32-1

2-CHLORO-N-METH...

~%

(2-Ethylphenyl)methylamine Structure

1821-38-1

(2-Ethylphenyl)...

N-methyl-N-(o-chlorophenyl)-4-amino-2-butenenitrile Structure

101195-40-8

N-methyl-N-(o-c...

~51%

1-Methylindole-3-acetonitrile Structure

51584-17-9

1-Methylindole-...

N-methyl-N-(3-cyanopropyl)-o-chloroaniline Structure

101195-50-0

N-methyl-N-(3-c...

N/A Structure

101195-49-7

N/A

2-CHLORO-N-METHYLANILINE Structure

932-32-1

2-CHLORO-N-METH...

~%

1-Methylindole-3-acetonitrile Structure

51584-17-9

1-Methylindole-...

N-(β-cyanoethyl)-N-(o-chlorophenyl)-4-amino-2-butenenitrile Structure

101195-43-1

N-(β-cyanoethyl...

~0%

3-(3-Methyl-1H-indol-1-yl)propanenitrile Structure

4414-81-7

3-(3-Methyl-1H-...

N/A Structure

101195-51-1

N/A

1-(β-cyanoethyl)-2,3-dihydroindole-3-acetonitrile Structure

101195-52-2

1-(β-cyanoethyl...

N-(β-cyanoethyl)-N-(o-chlorophenyl)-4-amino-2-butenenitrile Structure

101195-42-0

N-(β-cyanoethyl...

~6%

3-(3-Methyl-1H-indol-1-yl)propanenitrile Structure

4414-81-7

3-(3-Methyl-1H-...

N/A Structure

101195-51-1

N/A

1-(β-cyanoethyl)-2,3-dihydroindole-3-acetonitrile Structure

101195-52-2

1-(β-cyanoethyl...

3-[(2-Chlorophenyl)Amino]Propanenitrile Structure

94-89-3

3-[(2-Chlorophe...

~%

3-(3-Methyl-1H-indol-1-yl)propanenitrile Structure

4414-81-7

3-(3-Methyl-1H-...

N-(β-cyanoethyl)-N-(o-chlorophenyl)-4-amino-2-butenenitrile Structure

101195-42-0

N-(β-cyanoethyl...

~%

3-(3-Methyl-1H-indol-1-yl)propanenitrile Structure

4414-81-7

3-(3-Methyl-1H-...

N/A Structure

101195-51-1

N/A

N-(Δ2-cyclohexenyl)-o-chloroaniline Structure

84487-67-2

N-(Δ2-cyclohexe...

~25%

N-cyclohex-2-en-1-ylaniline Structure

52034-22-7

N-cyclohex-2-en...

N/A Structure

101195-54-4

N/A

2-Chloroaniline Structure

95-51-2

2-Chloroaniline

~%

N-cyclohex-2-en-1-ylaniline Structure

52034-22-7

N-cyclohex-2-en...

3-Bromocyclohexene Structure

1521-51-3

3-Bromocyclohexene

~%

N-cyclohex-2-en-1-ylaniline Structure

52034-22-7

N-cyclohex-2-en...

2-(2-cyclohexen-1-yl)acetyl chloride Structure

3514-86-1

2-(2-cyclohexen...

2-Chloroaniline Structure

95-51-2

2-Chloroaniline

~%

N-(2-chlorophenyl)-2-cyclohex-2-en-1-ylacetamide Structure

101195-46-4

N-(2-chlorophen...

2'-Chloroacetanilide Structure

533-17-5

2'-Chloroacetanilide

~%

2-(1-acetylindol-3-yl)acetonitrile Structure

62485-98-7

2-(1-acetylindo...


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