Synthesis of N-Bn-3-substituted-2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones 10 from 1 and N-Bn-α-amino acid methyl ester 9a.
Entryb | R1 | R2 | 1 | R3 | R4 | 9 | t (h) | 10 (%) |
---|---|---|---|---|---|---|---|---|
1 | H | H | 1a | CH2Ph | Me | 9a | 24 | 84 10a |
2 | H | H | 1a | CH(CH3)2 | Et | 9b | 48 | 71 10b |
3 | H | H | 1a | CH(CH3)(C2H5) | Me | 9c | 16 | 67 10c |
4 | Cl | H | 1d | CH(CH3)(C2H5) | Me | 9c | 17 | 54 10d |
5 | OMe | H | 1c | CH2Ph | Me | 9a | 16 | 68 10e |
Unless otherwise stated, reactions were carried out on a 0.290 mmol scale at 120 °C using 1.5 equiv. of 9, 2 equiv. of K2CO3 in 3.0 mL of MeCN.
Yields are given for isolated products.