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Synthesis 2009(20): 3439-3442
DOI: 10.1055/s-0029-1216973
DOI: 10.1055/s-0029-1216973
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Regioselectivity Change in the Reaction of Naphthalene and 2-Naphthyl Ethers with 1,3,5-Triazines Depending on Reagent Quantities
Weitere Informationen
Received
8 June 2009
Publikationsdatum:
28. August 2009 (online)
Publikationsverlauf
Publikationsdatum:
28. August 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200920/lookinside/thumbnails/10.1055-s-0029-1216973-1.jpg)
Abstract
A new method for the synthesis of 4H-benzo[de]isoquinolin-4-ones has been developed, based on the reaction of 2-naphthyl ethers with an equimolar quantity of 1,3,5-triazines in polyphosphoric acid. With a 2.5 molar excess of 1,3,5-triazines in polyphosphoric acid, the products of 1,6-diacylation (diformylation) are formed. Isoquino[6′,5′,4′:10,5,6]anthra[2,1,9-def]isoquinoline is formed upon reaction of a 1.5 molar excess of 1,3,5-triazine with naphthalene in polyphosphoric acid at 130-140 ˚C.
Key words
1,3,5-triazines - polyphosphoric acid - naphthalenes - acylation - 4H-benzo[de]isoquinolin-4-ones - isoquino[6′,5′,4′:10,5,6]anthra[2,1,9-def]isoquinoline
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