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. 2023 Mar 29;13(15):10090–10096. doi: 10.1039/d3ra01335a

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.

graphic file with name d3ra01335a-u3.jpg
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
a

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.

b

Yields are given for isolated products.