Tandem directed metalation reactions. Short syntheses of polycyclic aromatic hydrocarbons and ellipticine alkaloids

M Watanabe, V Snieckus

Index: Watanabe; Snieckus Journal of the American Chemical Society, 1980 , vol. 102, # 4 p. 1457 - 1460

Full Text: HTML

Citation Number: 103

Abstract

(8) G. Fachinetti, J. Chem. SOC., Chem. Commun., 397 (1979).(9)[PPN] 2 [Fe4C0) 13] was synthesized by a modification of the procedure by W. Hieber and R. Werner, Chem. Ber., 90, 286 (1957); the structure of the anion is reported by RJ Dodens and LF Dahl, J. Am. Chem. SOC., 88, 4847 (1966).

 Related Synthetic Route
Benzophenone Structure

119-61-9

Benzophenone

N,N-DIETHYLBENZAMIDE Structure

1696-17-9

N,N-DIETHYLBENZAMIDE

~14%

10-hydroxy-10-phenyl-anthracen-9-one Structure

5146-30-5

10-hydroxy-10-p...

1,2:5,6-Dibenz-9, 10-anthraquinone Structure

3719-43-5

1,2:5,6-Dibenz-...

~44%

Benzo[a]tetracene Structure

226-88-0

Benzo[a]tetracene

3-Thiophenecarboxaldehyde Structure

498-62-4

3-Thiophenecarb...

1-Naphthalenecarboxamide,N,N-diethyl- Structure

5454-10-4

1-Naphthaleneca...

~37%

naphtho[2,1-f][1]benzothiole-7,11-dione Structure

7495-38-7

naphtho[2,1-f][...

N,N-DIETHYLBENZAMIDE Structure

1696-17-9

N,N-DIETHYLBENZAMIDE

o-Anisaldehyde Structure

135-02-4

o-Anisaldehyde

~10%

1-Methoxyanthraquinone Structure

82-39-3

1-Methoxyanthra...

METHYLLITHIUM Structure

917-54-4

METHYLLITHIUM

6-benzyl-6H-pyrido[4,3-b]carbazole-5,11-dione Structure

73540-74-6

6-benzyl-6H-pyr...

~%

ELLIPTICINE Structure

519-23-3

ELLIPTICINE

6H-Pyrido[4,3-b]carbazole, 5,11-dimethyl-6-(phenylmethyl)- Structure

74606-36-3

6H-Pyrido[4,3-b...

N,N-DIETHYLBENZAMIDE Structure

1696-17-9

N,N-DIETHYLBENZAMIDE

Acetophenone Structure

98-86-2

Acetophenone

~17%

10-hydroxy-10-methylanthracen-9-one Structure

17104-31-3

10-hydroxy-10-m...

N,N-DIETHYLBENZAMIDE Structure

1696-17-9

N,N-DIETHYLBENZAMIDE

4-Methoxybenzaldehyde Structure

123-11-5

4-Methoxybenzal...

~28%

2-METHOXYANTHRAQUINONE Structure

3274-20-2

2-METHOXYANTHRA...

1,2:5,6-Dibenz-9, 10-anthraquinone Structure

3719-43-5

1,2:5,6-Dibenz-...

~86%

Benzo[k]tetraphene Structure

53-70-3

Benzo[k]tetraphene

benzo[b]triphenylene-9,14-dione Structure

3228-74-8

benzo[b]triphen...

~45%

Benzo[f]tetraphene Structure

215-58-7

Benzo[f]tetraphene

N,N-DIETHYLBENZAMIDE Structure

1696-17-9

N,N-DIETHYLBENZAMIDE

p-Tolualdehyde Structure

104-87-0

p-Tolualdehyde

~15%

Tectoquinone Structure

84-54-8

Tectoquinone

3-Thiophenecarboxaldehyde Structure

498-62-4

3-Thiophenecarb...

N,N-DIETHYLBENZAMIDE Structure

1696-17-9

N,N-DIETHYLBENZAMIDE

~34%

Naphtho(2,3-b)thiophene-4,9-dione Structure

4968-81-4

Naphtho(2,3-b)t...

N-(methoxymethyl)-3-indolecarboxaldehyde Structure

73540-77-9

N-(methoxymethy...

~%

ELLIPTICINE Structure

519-23-3

ELLIPTICINE

METHYLLITHIUM Structure

917-54-4

METHYLLITHIUM

6-(methoxymethyl)-6H-pyrido[4,3-b]carbazole-5,11-dione Structure

73540-73-5

6-(methoxymethy...

~%

ELLIPTICINE Structure

519-23-3

ELLIPTICINE

METHYLLITHIUM Structure

917-54-4

METHYLLITHIUM

6-benzyl-6H-pyrido[4,3-b]carbazole-5,11-dione Structure

73540-74-6

6-benzyl-6H-pyr...

~%

ELLIPTICINE Structure

519-23-3

ELLIPTICINE

6H-Pyrido[4,3-b]carbazole, 5,11-dimethyl-6-(phenylmethyl)- Structure

74606-36-3

6H-Pyrido[4,3-b...


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