Mild and Simple Access to Diverse 4-Amino-substituted 2-Phenyl-1,2,3,4-tetrahydroquinolines and 2-Phenylquinolines Based on a Multicomponent Imino Diels-Alder Reaction

作者：Varma P Prabhakara^*; Sherigara Bailure S; Mahadevan Kittappa M; Hulikal Vijaykumar

来源：Synthetic Communications, 2010, 40(15): 2220-2231.

DOI：10.1080/00397910903221035

• Antimony trichloride
• 2-phenylquinolines
• tetrahydroquinoline
• N-vinylcaprolactam
• N-vinylpyrrolidin-2-one

A straightforward synthesis of new 1-(2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-ones/azepan-2-one from N-vinyl caprolactam/N-vinylpyrrolidin-2-one and N-benzylideneaniline via the imino Diels-Alder reaction has been reported for the first time. Antimony(III) chloride has been shown to effectively catalyze imino-Diels-Alder reaction to afford both 2-phenylquinoline and 2-phenyl-1,2,3,4-tetrahydroquinolin derivatives in excellent yields at ambient temperature. The cis diastereoselectivity to give cis 2-phenyl-1,2,3,4-tetrahydroquinolines is also highlighted in this reaction.

• 出版日期2010