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首页> 外文期刊>The Journal of Organic Chemistry >Rearrangements and intramolecular diels-alder reactions of normal and vinylogous aza-morita-baylis-hillman products leading to isoindoline derivatives
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Rearrangements and intramolecular diels-alder reactions of normal and vinylogous aza-morita-baylis-hillman products leading to isoindoline derivatives

机译：正常和含乙烯基的aza-morita-baylis-hillman产品的重排和分子内diels-alder反应导致异吲哚啉衍生物

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摘要

Figure presented Aza-Morita-Baylis-Hillman (aza-MBH) products derived from arylimines and methyl acrylate or acrylonitrile were N-alkylated with (E)-5-bromopenta-1,3-diene, and the resulting trienes were subjected to intramolecular Diels-Alder (IMDA) cyloadditions to afford the corresponding trans- and cis-fused tetrahydroisoindolines as the major and minor products, respectively. Catalysis with boron trichloride improved the IMDA diastereoselectivities of the nitrile derivatives, while yields were improved in both the nitrile and ester series. Treatment of the nitrile-substituted trienes with DABCO in DMF resulted in unexpected transposition of the N-(pentadienyl)sulfonamide group to the β-position of the acrylonitrile moiety. Subsequent IMDA cycloadditions produced cis-fused positional isomers of the previous tetrahydroisoindolines. When the products of vinylogous aza-MBH reactions in the nitrile series were N-propargylated, the resulting dienynes underwent a similar transposition and IMDA reaction, producing trans and cis diastereomers of the corresponding dihydroisoindolines as the major and minor products, respectively. In all but one case, only the former products were observed in the presence of methylaluminum dichloride, while the corresponding aromatized isoindolines were obtained when the IMDA reactions were carried out in the presence of DDQ. Thus, a variety of aryl-substituted isoindoline products with different levels of unsaturation and complementary substitution patterns and stereochemistry are readily available through these processes.
机译：该图显示了衍生自芳丙胺和丙烯酸甲酯或丙烯腈的Aza-Morita-Baylis-Hillman（aza-MBH）产品经（E）-5-bromopenta-1,3-diene N-烷基化，所得三烯经过分子内处理Diels-Alder（IMDA）缩聚反应分别提供相应的反式和顺式融合的四氢异二氢吲哚作为主要产物和次要产物。三氯化硼催化提高了腈衍生物的IMDA非对映选择性，而腈和酯系列的收率均得到提高。在DMF中用DABCO处理腈取代的三烯导致N-（戊二烯基）磺酰胺基团意外地转位到丙烯腈部分的β位。随后的IMDA环加成产生了先前四氢异二氢吲哚的顺式-融合位置异构体。当腈系列中的含乙烯基氮杂-MBH反应的产物进行N-炔丙基化时，所得二烯进行相似的易位和IMDA反应，分别产生相应的二氢异二氢吲哚的反式和顺式非对映异构体，分别作为主要产物和次要产物。在除一种情况外的所有情况下，在二氯化甲基铝存在下仅观察到前一种产物，而在DDQ存在下进行IMDA反应则获得了相应的芳香化异吲哚啉。因此，通过这些方法可以容易地获得具有不同水平的不饱和度和互补取代模式以及立体化学的各种芳基取代的异吲哚啉产物。

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