Novel domino reactions in β-carbolines with triple bonded dienophiles

✍ Scribed by Álvaro González-Gómez; Gema Domínguez; Ulises Amador; Javier Pérez-Castells

• Book ID: 104095597
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 245 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.07.025

✦ Synopsis

Vinylpyrrolo-[2,1-a]-b-carbolines 1 give different products upon reaction with dienophiles. With dimethyl acetylenedicarboxylate (DMAD), a novel domino process takes place, involving Michael attack and rearrangement, affording complex polycycles like 3, 4, and 5. Diels-Alder cycloadditions are favored in the presence of Lewis acids and are the only reactions with dimethyl maleate. When 3-butyn-2-one is used as dienophile, a Stevens rearrangement is observed giving product 9.