5,6-未取代的1,4-二氢吡啶在惠斯根1,4-偶极环加成反应和形式上的[2 + 2]环加成反应中的独特反应活性。
The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition.
作者信息
Chen Xiu-Yu, Zheng Hui, Han Ying, Sun Jing, Yan Chao-Guo
机构信息
College of Chemistry & Chemical Engineering, Yangzhou University, Jiangsu, Yangzhou 225002, China.
出版信息
Beilstein J Org Chem. 2023 Jun 29;19:982-990. doi: 10.3762/bjoc.19.73. eCollection 2023.
The three-component reaction of isoquinolines, dialkyl acetylenedicarboxylates, and 5,6-unsubstituted 1,4-dihydropyridines in acetonitrile at room temperature afforded functionalized isoquinolino[1,2-][1,6]naphthyridines in good yields and with high diastereoselectivity. More importantly, the formal [2 + 2] cycloaddition reaction of dialkyl acetylenedicarboxylates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile gave unique 2-azabicyclo[4.2.0]octa-3,7-dienes as major products and 1,3a,4,6a-tetrahydrocyclopenta[]pyrroles as minor products via further rearrangement.
异喹喹啉、二烷基乙炔二羧酸酯和5,6-未取代的1,4-二氢吡啶在室温下于乙腈中发生的三组分反应，以良好的产率和高非对映选择性得到了官能化的异喹啉并[1,2 - ][1,6]萘啶。更重要的是，二烷基乙炔二羧酸酯和5,6-未取代的1,4-二氢吡啶在回流的乙腈中发生的形式上的[2 + 2]环加成反应，通过进一步重排，以独特的2-氮杂双环[4.2.0]辛-3,7-二烯作为主要产物，1,3a,4,6a-四氢环戊并[]吡咯作为次要产物。
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