Synthesis of 6-substituted tetrahydropyridinones and cyclization to indolizidine and quinolizidine structures

✍ Scribed by Shang-Shing P. Chou; Hao-Chieh Chiu; Chia-Cheng Hung

• Book ID: 104253791
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 170 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)01096-7

✦ Synopsis

3-Sulfolenes 1 with various substituents at C-2 underwent [4+2] cycloaddition reactions with p-toluenesulfonyl isocyanate to give the teterahydropyridinones 4. Through N-detosylation and Hg(II)-mediated electrophilic addition/intramolecular cyclization of 4e and 4f, the indolizidine and quinolizidine compounds 7a/7b and 8 were synthesized, respectively.