Research Article

Synthesis of 1,2-Dihydro-Substituted Aniline Analogues Involving N-Phenyl-3-aza-Cope Rearrangement Using a Metal-Free Catalytic Approach

Table 2

Scope of the annulation reaction of N-propargyl vinyl anilines.

EntryPropargyl acetateAnilineMichael acceptorsaPropargyl vinyl amine1,2-DihydropyridineYield (%)b

1Anilinea95
2p-Anisidinea88
3ā€‰4-Bromo anilinea76
4p-Anisidineb48
5p-Anisidineb56
6Anilinea81
7p-Anisidineb85
8Anilineb70
9p-Anisidineb84
10Anilineb92
11Anilinec68
12Anilinec61

a, ; b, ; c, ; isolated yields by column chromatography.