Detail of "14920-81-1"

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Annulation reactions leading to naphthalene derivatives

Annulation reactions leading to naphthalene derivatives. New syntheses of natural 1,2- and 1,4-naphthoquinones. Ghera, Eugene; Ben-David, Yoshua (Dep. Org. Chem.Chemical with cas number 14920-81-1 also plays role., Weizmann Inst. Sci., Rehovot 76100, Israel). J. Org. Chem., 50(18), 3355-9 (English) 1985. CODEN: JOCEAH. ISSN: 0022-3263. DOCUMENT TYPE: Journal CA Section: 26 (Biomolecules and Their Synthetic Analogs) Section cross-reference(s): 25 1-(Phenylsulfonyl)-2-oxo-3-(methoxycarbonyl)-1,2,3,4-tetrahydronaphtha lene derivs. with various C-3 substituents were effectively prepd. by a one-step cyclization involving 1-[(phenylsulfonyl)methyl]-2-bromomethylbenzene derivs. and monosubstituted malonic esters. A high yield one-step decarboxylation-desulfonylation of the above products by LiI led to C-3-substituted 2-naphthalenols (I) whereas prior C-1 alkylation of the cyclization products provided 1,3-dialkylated 2-naphthalenols. Oxidns. of I to o-naphthoquinones and further oxidns. of the above products to substituted 2-hydroxy-1,4-naphthoquinones provided a new pathway to naturally occurring naphthoquinones like phthiocol (II, R = H, R1 = Me) droserone Me ether (II, R = MeO, R1 = Me) and lapachol (II, R = H, R1 = Me2C:CHCH2). .