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. 2021 May 26;11(31):19121–19127. doi: 10.1039/d1ra02347k

Tandem imines formation via auto-hydrogen transfer from alcohols to nitro compounds catalyzed by Cu-isatin Schiff base-γ Fe2O3.

graphic file with name d1ra02347k-u2.jpg
Entrya R1 R2 Product Time (h) Yield (%)
1 C6H5 C6H5 a 10 92
2 C6H5 4-OH–C6H4 b 8 90
3 C6H5 4-OMe–C6H4 c 8 84
4 C6H5 4-Me–C6H4 d 9 87
5 C6H5 4-Cl–C6H4 e 12 71
6 4-Me–C6H4 C6H5 f 13 91
7 4-Me–C6H4 4-Cl–C6H4 g 12 68
8 4-Me–C6H4 4-OMe–C6H4 h 10 85
9 4-Me–C6H4 4-Me–C6H4 i 12 83
10 4-OMe–C6H4 C6H5 j 12 75
11 4-OMe–C6H4 4-Cl–C6H4 k 13 72
12 4-OMe–C6H4 4-OMe–C6H4 l 11 84
13 4-OMe–C6H4 4-Me–C6H4 m 14 70
14 C6H5 CH3–CH2 n 10 72
15 CH3–CH3–CH2 C6H5 o 12 85
a

Reaction conditions: nitro compound (1 mmol), alcohol (1 mmol), KOH (1 mmol), solvent-free, catalyst (1 mol%), 100 °C. Melting points of the solid products were compared with the reported ones in the ESI (Table S1).