A new coumarin synthesis and its utilization for the synthesis of polycyclic coumarin compounds with anticarcinogenic properties

RG Harvey, C Cortez, TP Ananthanarayan…

Index: Harvey; Cortez; Ananthanarayan; Schmolka Journal of Organic Chemistry, 1988 , vol. 53, # 17 p. 3936 - 3943

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Citation Number: 84

Abstract

A novel synthesis of coumarins based on the ortho-directed metalation of methoxymethyl phenolic ethers with alkyllithium reagents is described. The method entails reaction of the ortho-lithiated intermediates with dimethylformamide to yield the corresponding ortho- aldehydes. Reaction of the latter with lithio-N, N-dimethylacetamide affords the addition products which on heating in refluxing acetic acid undergo smooth conversion directly to ...

 Related Synthetic Route
3-(5-chloro-2-(methoxymethoxy)phenyl)-3-hydroxy-N,N-dimethylpropanamide Structure

115560-50-4

3-(5-chloro-2-(...

~60%

2H-1-Benzopyran-2-one,6-chloro- Structure

2051-59-4

2H-1-Benzopyran...

4-Chlorophenol Structure

106-48-9

4-Chlorophenol

~%

2H-1-Benzopyran-2-one,6-chloro- Structure

2051-59-4

2H-1-Benzopyran...

4-Chloro-1-(methoxymethoxy)benzene Structure

826-26-6

4-Chloro-1-(met...

~%

2H-1-Benzopyran-2-one,6-chloro- Structure

2051-59-4

2H-1-Benzopyran...

4-Chlorophenol Structure

106-48-9

4-Chlorophenol

~%

5-chloro-2-(methoxymethoxy)benzaldehyde Structure

115560-38-8

5-chloro-2-(met...

4-Chloro-1-(methoxymethoxy)benzene Structure

826-26-6

4-Chloro-1-(met...

N,N-Dimethylformamide Structure

68-12-2

N,N-Dimethylfor...

~%

5-chloro-2-(methoxymethoxy)benzaldehyde Structure

115560-38-8

5-chloro-2-(met...

2-Hydroxy-naphthaldehyde Structure

708-06-5

2-Hydroxy-napht...

~%

3H-naphtho(2,1-b)pyran-3-one Structure

4352-89-0

3H-naphtho(2,1-...

p-Cresol Structure

106-44-5

p-Cresol

~%

2-(methoxymethoxy)benzaldehyde Structure

5533-04-0

2-(methoxymetho...

1-(Methoxymethoxy)-4-methylbenzene Structure

25458-49-5

1-(Methoxymetho...

N,N-Dimethylformamide Structure

68-12-2

N,N-Dimethylfor...

~%

2-(methoxymethoxy)benzaldehyde Structure

5533-04-0

2-(methoxymetho...

3-hydroxy-3-(2-(methoxymethoxy)-4-methylphenyl)-N,N-dimethylpropanamide Structure

115560-73-1

3-hydroxy-3-(2-...

~91%

7-Methylcoumarin Structure

2445-83-2

7-Methylcoumarin

1-Hydroxypyrene Structure

5315-79-7

1-Hydroxypyrene

~%

8-methylpyreno[1,2-b]pyran-9-one Structure

115560-63-9

8-methylpyreno[...


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