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One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes.
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-07-22 , DOI: 10.3762/bjoc.16.150 Haruyasu Asahara 1, 2, 3 , Minami Hiraishi 1 , Nagatoshi Nishiwaki 1, 2
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-07-22 , DOI: 10.3762/bjoc.16.150 Haruyasu Asahara 1, 2, 3 , Minami Hiraishi 1 , Nagatoshi Nishiwaki 1, 2
Affiliation
β-Nitrostyrenes underwent a Diels–Alder reaction with Danishefsky’s diene to afford cyclohexenes together with the corresponding hydrolyzed products, 3-arylated-5-methoxy-4-nitrocyclohexanones. When the reaction was conducted in the presence of water, the cyclohexenes were efficiently hydrolyzed into cyclohexanones. Subsequent aromatization by heating the cyclohexanone with a catalytic amount of iodine in dimethyl sulfoxide gave 3-arylated-4-nitrophenols. The reaction of nitrostyrenes with Danishefsky’s diene could be conducted in one pot to directly afford the corresponding nitrophenols. Moreover, a heteroaryl group, e.g., a thienyl group could be introduced into the nitrophenol framework.
中文翻译:
通过多官能化的环己酮从β-硝基苯乙烯一锅无金属地合成3-芳基-4-硝基苯酚
β-硝基苯乙烯与Danishefsky的二烯进行Diels-Alder反应,得到环己烯以及相应的水解产物3-芳基-5-甲氧基-4-硝基环己酮。当反应在水的存在下进行时,环己烯被有效地水解成环己酮。随后通过将环己酮与催化量的碘在二甲基亚砜中加热来进行芳构化,得到3-芳基-4-硝基苯酚。硝基苯乙烯与Danishefsky的二烯的反应可以在一个罐中进行,以直接提供相应的硝基酚。此外,可以将杂芳基,例如噻吩基引入到硝基酚骨架中。
更新日期:2020-07-22
中文翻译:
通过多官能化的环己酮从β-硝基苯乙烯一锅无金属地合成3-芳基-4-硝基苯酚
β-硝基苯乙烯与Danishefsky的二烯进行Diels-Alder反应,得到环己烯以及相应的水解产物3-芳基-5-甲氧基-4-硝基环己酮。当反应在水的存在下进行时,环己烯被有效地水解成环己酮。随后通过将环己酮与催化量的碘在二甲基亚砜中加热来进行芳构化,得到3-芳基-4-硝基苯酚。硝基苯乙烯与Danishefsky的二烯的反应可以在一个罐中进行,以直接提供相应的硝基酚。此外,可以将杂芳基,例如噻吩基引入到硝基酚骨架中。