88116-06-7Relevant academic research and scientific papers
Annulation Reactions Leading to Naphtalene Derivatives. New Syntheses of Natural 1,2- and 1,4-Naphthoquinones
Ghera, Eugene,Ben-David, Yoshua
, p. 3355 - 3359 (2007/10/02)
1-(Phenylsulfonyl)-2-oxo-3-(methoxycarbonyl)-1,2,3,4-tetrahydronaphthalene derivatives with various C-3 substituents were effectively prepared by a one-step cyclization involving 1--2-(bromomethyl)benzene derivatives and monosubstituted malonic esters.A high yield one-step decarboxylation-desulfonylation of the above products by lithium iodide led to C-3-substituted 2-naphthalenols 7a-g whereas prior C-1 alkylation of the cyclization products provided 1,3-dialkylated 2-naphthalenols 6s,b.Oxidations of compounds 7 to o-naphthoquinones 8a-f further oxidations of the above products to substituted 2-hydroxy-1,4-naphthoquinones provided a new pathway to naturally occuring naphthoquinones like phthiocol (9), droserone methyl ether (10), and lapachol (15).
NEW ANNULATION METHODS OF AROMATIC RINGS. NEW SYNTHESIS OF NAPHTHALENE, ANTHRACENE AND PHENANTHRENE STRUCTURES.
Ghera, Eugene,Ben-David, Yehoshua
, p. 3533 - 3536 (2007/10/02)
Condensation of 2-(phenylsulfonyl)methyl benzyl bromide and its derivatives with malonates, 1,3-ketoesters and lactones resulted in the regioselective formation of naphthalene derivatives and of other polycyclic systems.
