Phthalazines. XIV. Reaction of Phthalazine 2-Oxide with Acetylenic Dienophiles
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Hetero-Diels-Alder reactions of hetaryl-thiochalcones with acetylenic dienophiles
Hetaryl-substituted thiochalcones react with acetylenic monoand diesters in the THF solution in the presence of LiClO4 at 65°C to give, after 24h, 4H-thiopyran carboxylates and dicarboxylates, respectively, in moderate to good yields. The same reactions were performed also in the THF solution without a catalyst under microwave irradiation. In that case, the reaction time was reduced to three mi...
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Selected hetaryl and aryl thioketones react with acetylenecarboxylates under thermal conditions in the presence of LiClO4 or, alternatively, under high-pressure conditions (5 kbar) at room temperature yielding thiopyran derivatives. The hetero-Diels-Alder reaction occurs in a chemo- and regioselective manner. The initially formed [4 + 2] cycloadducts rearrange via a 1,3-hydrogen shift sequence ...
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Substituted pyrroles were prepared by a gold(I)-catalyzed acetylenic Schmidt reaction of homopropargyl azides. The reaction allows for regiospecific substitution at each position of the pyrrole ring under mild conditions. A mechanism in which azides serve as nucleophiles toward gold(I)-activated alkynes with subsequent gold(I)-aided expulsion of dinitrogen is proposed.
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The Diels-Alder reactions of maleimide with the acetonide derivative (6a) of cis-3,5-cyclohexadiene-1,2-diol (1a) in various solvents showed facial selectivities ranging from 1 : 1 to 1 : 9. The same derivative 6a reacted in benzene with ethylenic dienophiles with generally modest facial selectivity, but acetylenic dienophiles added exclusively anti to the oxygen functions of 6a. Dimerization o...
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The adducts produced in the reaction between trialkyl phosphites and acetylenic esters were trapped by hydantoins to produce highly functionalized dialkyl 2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl) succinate in good yields.
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ژورنال
عنوان ژورنال: YAKUGAKU ZASSHI
سال: 1983
ISSN: 0031-6903,1347-5231
DOI: 10.1248/yakushi1947.103.1_34