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

Synthesis of polycyclic aromatic hydrocarbons via a novel annelation method

RG Harvey, C Cortez, SA Jacobs

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

Full Text: HTML

Citation Number: 28

Abstract

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) Structure

acetic acid-(14...

~92%

14-methylnaphtho[1,2-b]phenanthrene Structure

14-methylnaphth...

14-acetoxy-7-methyldibenz[a,j]anthracene Structure

14-acetoxy-7-me...

~98%

7-Methyldibenz(a,j)anthracene Structure

7-Methyldibenz(...

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

3-Methyl-3-phen...

~93%

2-(1-phenylethyl)naphthalene-1-carboxylic acid Structure

2-(1-phenylethy...

naphthoic acid Structure

~%

2-(1-phenylethyl)naphthalene-1-carboxylic acid Structure

2-(1-phenylethy...

1-Naphthoyl chloride Structure

1-Naphthoyl chloride

~%

2-(1-phenylethyl)naphthalene-1-carboxylic acid Structure

2-(1-phenylethy...

11,12-dihydrobenzo[a]pyrene Structure

11,12-dihydrobe...

~%

Benzo(a)pyrene Structure

naphthoic acid Structure

~%

1-Naphthalenecarboxamide,N,N-diethyl- Structure

1-Naphthaleneca...

1-Naphthalenecarboxamide,N,N-diethyl- Structure

1-Naphthaleneca...

~%

2-(1-phenylethyl)naphthalene-1-carboxylic acid Structure

2-(1-phenylethy...

naphthoic acid Structure

~%

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

3-Methyl-3-phen...

1-Naphthoyl chloride Structure

1-Naphthoyl chloride

~%

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

3-Methyl-3-phen...

1-Naphthalenecarboxamide,N,N-diethyl- Structure

1-Naphthaleneca...

Acetophenone Structure

~%

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

3-Methyl-3-phen...

dibenz[a.h]anthracen-7-ol acetate Structure

dibenz[a.h]anth...

~93%

Benzo[k]tetraphene Structure

Benzo[k]tetraphene

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

3-[1]naphthyl-3...

~53%

Benzo[k]tetraphene Structure

Benzo[k]tetraphene

14-acetoxydibenz(a,j)anthracene Structure

14-acetoxydiben...

~89%

Benzo[m]tetraphene Structure

Benzo[m]tetraphene

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

3-(naphthalen-2...

~80%

Benzo[m]tetraphene Structure

Benzo[m]tetraphene

naphthoic acid Structure

~%

Benzo[m]tetraphene Structure

Benzo[m]tetraphene

1-Naphthalenecarboxamide,N,N-diethyl- Structure

1-Naphthaleneca...

~%

Benzo[m]tetraphene Structure

Benzo[m]tetraphene

1-Naphthoyl chloride Structure

1-Naphthoyl chloride

~%

Benzo[m]tetraphene Structure

Benzo[m]tetraphene

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

Benz[a]anthrace...

~86%

7-Methyltetraphene Structure

7-Methyltetraphene

Synthesis of 3-methylcholanthrene

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