Studies of chemoselectivity in Diels-Alder reactions of 2-(p- tolylsulfinyl)-1,4-benzoquinone and styrenes: Formation of (p-tolylsulfinyl)- 1,4-phenanthrenequinones
Diels-Alder reactions of 2-(p-tolylsulfinyl)-1,4-benzoquinone 1 with 4- methoxystyrenes 2a-b in polar solvents afforded 2- and 3-(p-tolylsulfinyl)- 1,4-phenanthrenequinones 4a-b and 5a-b as major compounds. A second cycloaddition of 5a and 4a with 3,4-dimethoxystyrene 2a gave access to C- and S-shaped pentacyclic molecules 10 and 11 in a highly regioselective way. (C) 2000 Elsevier Science Ltd.
Synthesis of 1,4-phenanthrenequinones via stannic chloride-induced cyclizations
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Kraus, George A.,Melekhov, Alex
p. 1720 - 1722
(2007/10/03)
Improved synthesis of 1,4-phenanthrenequinones from Diels-Alder cycloadditions of 2-(p-Tolylsulfinyl)-1,4-benzoquinone
A wide range of substituted 1,4-phenanthrenequinones 5a-g and benz[c]- and benz[a]-1,4-phenanthrenequinones (5h) and (5i) were synthezised in one step through Diels-Alder cycloadditions of 2-(p-tolylsulfinyl)-1,4-benzoquinone 2 and vinylaromatic derivatives 1a-i under thermal and high pressure conditions in moderate to good yields (33-80%).
Carreno, M. Carmen,Mahugo, Jesus,Urbano, Antonio
p. 3047 - 3050
(2007/10/03)
Improved Synthesis of Methoxy-1,4-phenanthraquinones
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Manning, Wayne B.,Kelly, Terence P.,Muschik, Gary M.
p. 2535 - 2536
(2007/10/02)
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