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Carbanion induced, base-catalyzed, synthesis of highly functionalized 8-aryl-3,4-dihydro-2(1H)-naphthalenones from 2H-pyran-2-ones

✍ Scribed by Vishnu Ji Ram; Nidhi Agarwal; Farhanullah


Book ID
104250947
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
83 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


A general and efficient synthesis of 8-aryl-5-methoxycarbonyl-6-methylsulfanyl-3,4-dihydro-2(1H)-naphthalenones 4a-i and 8-aryl-5-cyano-6-sec-amino-3,4-dihydro-2(1H)-naphthalenones 4l-r has been delineated from the acid hydrolysis of 8-aryl-5methoxycarbonyl-6-methylsulfanyl-3,4-dihydro-2(1H)-naphthalenone-(2,2-dimethyltrimethylene)ketals 3a-i and 8-aryl-5-cyano-6sec-amino-3,4-dihydro-2(1H)-naphthalenone-(2,2-dimethyltrimethylene) ketals 3l-r, obtained from the reaction of 6-aryl-3-methoxycarbonyl-4-methylsulfanyl-2H-pyran-2-ones 1a-i and 3-cyano-6-aryl-4-sec-amino-2H-pyran-2-ones 1l-r with 1,4-cyclohexanedione mono-(2,2-dimethyltrimethylene)ketal 2.


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