High-Pressure-Promoted Diels-Alder Approach to Biaryls: Application to the Synthesis of the Cannabinols Family
High-Pressure-Promoted Diels-Alder Approach to Biaryls: Application to the Synthesis of the Cannabinols Family
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DOI：
10.1021/jo301203k
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发表时间：
2012-09-21
影响因子：
3.6
通讯作者：
Ballerini, Eleonora
中科院分区：
文献类型：
--
作者：
Minuti, Lucio;Temperini, Andrea;Ballerini, Eleonora
研究了1-（烷氧基/烷基/卤素取代苯基）丁-1,3-二烯与丙酸甲酯在绿色乙醇介质中9 kbar压力下的Diels-Alder反应。使用高压作为Diels-Alder反应的激活方法，可以高效和区域选择性地生成一系列环己二烯-苯环加合物，这些环加合物被氧化成相应的双芳基。所制得的烷氧基/烷基基/卤素取代的双芳基是获得取代的6h -苯并[c]铬-6-酮和大麻酚家族的有用前体。
Diels-Alder reactions of a range of 1-(alkoxy/alkyl/halogen-substituted phenyl)buta-1,3-dienes with methyl propiolate carried out in a green ethanolic medium under 9 kbar pressure were investigated. The use of high pressure as activating method of the Diels-Alder reactions allows efficient and regioselective generation of a series of cyclohexadienyl-benzene cycloadducts that are oxidized to the corresponding biaryls. The alkoxy/alkyl/halogen-substituted biaryls produced are useful precursors for accessing substituted 6H-benzo[c]chromen-6-ones and the cannabinols family.