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Synthesis of polycyclic aromatic hydrocarbons via a novel annelation method

RG Harvey, C Cortez, SA Jacobs

文献索引：Harvey, Ronald G.; Cortez, Cecilia; Jacobs, Stephen A. Journal of Organic Chemistry, 1982 , vol. 47, # 11 p. 2120 - 2125

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被引用次数: 28

摘要

A new general synthetic approach to polycyclic aromatic hydrocarbons is described. The method is based on the convenient availability of o-lithioarylamides from regiospecific metalation of Nfl-diethylarylamides with alkyllithium-amine reagents. Addition of the o- lithioarylamide to an aryl ketone or aldehyde affords a lactone. Reduction of the latter with zinc and alkali or HI generates the free acid which undergoes cyclization with ZnClz and ...

acetic acid-(14-methyl-dibenz[a,h]anthracen-7-yl ester)结构式

acetic acid-(14...

~92%

14-methylnaphtho[1,2-b]phenanthrene结构式

14-methylnaphth...

14-acetoxy-7-methyldibenz[a,j]anthracene结构式

14-acetoxy-7-me...

~98%

7-Methyldibenz(a,j)anthracene结构式

7-Methyldibenz(...

3-Methyl-3-phenylnaphtho(1,2-c)furan-1(3H)-one结构式

3-Methyl-3-phen...

~93%

2-(1-phenylethyl)naphthalene-1-carboxylic acid结构式

2-(1-phenylethy...

1-萘甲酸结构式

~%

2-(1-phenylethyl)naphthalene-1-carboxylic acid结构式

2-(1-phenylethy...

1-萘甲酰氯结构式

~%

2-(1-phenylethyl)naphthalene-1-carboxylic acid结构式

2-(1-phenylethy...

11,12-dihydrobenzo[a]pyrene结构式

11,12-dihydrobe...

~%

苯并[a]芘结构式

1-萘甲酸结构式

~%

N,N-二乙基-1-萘羧酰胺结构式

N,N-二乙基-1-萘羧酰胺

N,N-二乙基-1-萘羧酰胺结构式

N,N-二乙基-1-萘羧酰胺

~%

2-(1-phenylethyl)naphthalene-1-carboxylic acid结构式

2-(1-phenylethy...

1-萘甲酸结构式

~%

3-Methyl-3-phenylnaphtho(1,2-c)furan-1(3H)-one结构式

3-Methyl-3-phen...

1-萘甲酰氯结构式

~%

3-Methyl-3-phenylnaphtho(1,2-c)furan-1(3H)-one结构式

3-Methyl-3-phen...

N,N-二乙基-1-萘羧酰胺结构式

N,N-二乙基-1-萘羧酰胺

苯乙酮结构式

~%

3-Methyl-3-phenylnaphtho(1,2-c)furan-1(3H)-one结构式

3-Methyl-3-phen...

dibenz[a.h]anthracen-7-ol acetate结构式

dibenz[a.h]anth...

~93%

二苯并(a,h)蒽结构式

二苯并(a,h)蒽

3-[1]naphthyl-3H-naphtho[1,2-c]furan-1-one结构式

3-[1]naphthyl-3...

~53%

二苯并(a,h)蒽结构式

二苯并(a,h)蒽

14-acetoxydibenz(a,j)anthracene结构式

14-acetoxydiben...

~89%

二苯并(a,j)蒽结构式

二苯并(a,j)蒽

3-(naphthalen-2-yl)naphtho[1,2-c]furan-1(3H)-one结构式

3-(naphthalen-2...

~80%

二苯并(a,j)蒽结构式

二苯并(a,j)蒽

1-萘甲酸结构式

~%

二苯并(a,j)蒽结构式

二苯并(a,j)蒽

N,N-二乙基-1-萘羧酰胺结构式

N,N-二乙基-1-萘羧酰胺

~%

二苯并(a,j)蒽结构式

二苯并(a,j)蒽

1-萘甲酰氯结构式

~%

二苯并(a,j)蒽结构式

二苯并(a,j)蒽

Benz[a]anthracen-12-ol, 7-methyl-, acetate结构式

Benz[a]anthrace...

~86%

7-甲基苯[a]蒽结构式

7-甲基苯[a]蒽

Synthesis of 3-methylcholanthrene

[Jacobs, Stephen A.; Harvey, Ronald G. Tetrahedron Letters, 1981 , vol. 22, p. 1093 - 1096]