A three-component domino protocol for the facile synthesis of highly functionalized tetrahydroisoquinolines by creation of their benzene ring

作者：Balamurugan Kamaraj; Jeyachandran Veerappan; Perumal Subbu^*; Carlos Menendez J

来源：Tetrahedron, 2011, 67(7): 1432-1437.

DOI：10.1016/j.tet.2010.12.052

A simple and efficient one-pot synthesis of novel 6-amino-8-aryl-2-methyl/benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline-5-carbonitriles from the reaction of 1-methyl/benzylpiperidin-4-one with beta-nitrostyrenes and malononitrile in the presence of morpholine is described. This transformation proceeds through the creation of three C=C bonds, leading to a new benzene ring, and presumably occurs via a domino sequence involving Knoevenagel, Michael, Thorpe-Ziegler, and dehydrogenation reactions.

• 出版日期2011-2-18