Photosensitized Diels–Alder reactions of N-arylimines: synthesis of tetrahydroquinoline derivatives

✍ Scribed by Wei Zhang; Xiaodong Jia; Li Yang; Zhong-Li Liu

• Book ID: 104252475
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 101 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02328-6

✦ Synopsis

Irradiation (u>345 nm) of catalytic amounts of 2,4,6-triphenylpyrylium tetrafluoroborate (TPT) in a CH 2 Cl 2 solution of N-aryl imines and a-methylstyrene or styrene produced the corresponding [4+2] cycloaddition products, tetrahydroquinoline derivatives, in good yield. The reaction was controlled by the relative oxidation potentials of the dienophile and the diene.