Table 1.
Comp.a | R | N‐alkyl | M.W. (g/mol) | Time, h | Yield, % b | M.p., °Cc |
---|---|---|---|---|---|---|
4aa | H | CH2=CHCH2 | 256 | 3 | 80 | Yellow oil |
4ab | CH3 | CH2=CHCH2 | 270 | 3 | 77 | Dark red oil |
4ac | OCH3 | CH2=CHCH2 | 286 | 3 | 84 | Orange oil |
4ad | Cl | CH2=CHCH2 | 290 | 3 | 93 | Red oil |
4ae | CH2CH3 | CH2=CHCH2 | 284 | 3 | 74 | Yellow oil |
4af | F | CH2=CHCH2 | 274 | 3 | 85 | Yellow oil |
4ag | Br | CH2=CHCH2 | 335 | 3 | 89 | Red oil |
4ba | H | HC≡CCH2 | 254 | 4 | 73 | 88–90 |
4bb | CH3 | HC≡CCH2 | 268 | 4 | 95 | 125–127 |
4bc | OCH3 | HC≡CCH2 | 284 | 4 | 92 | 123–125 |
4bd | Cl | HC≡CCH2 | 288 | 4 | 91 | 154–156 |
4be | CH2CH3 | HC≡CCH2 | 282 | 4 | 91 | 106–107 |
4bf | F | HC≡CCH2 | 272 | 4 | 85 | 131–132 |
4bg | Br | HC≡CCH2 | 333 | 4 | 93 | 118–120 |
Compounds 4aa‐ag were obtained using InCl3 (20 mol%) as catalyst, while compounds 4ba‐bg were obtained by using p‐TsOH (20 mol%).
Yields after column chromatography.
Uncorrected.