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. Author manuscript; available in PMC: 2013 Jul 29.
Published in final edited form as: Bioorg Med Chem Lett. 2010 Jun 10;20(15):4468–4471. doi: 10.1016/j.bmcl.2010.06.042

Table 1.

Reaction times and yields of 3-hydroxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)indolin-2-ones (3a-w)

Compd R1 R2 R3 Method-A Method-B

Yield (%) Time (sec) Yield (%) Time (hr)
3a H H H 92 20 80 6
3b F H H 94 30 81 6
3c Cl H H 91 40 78 6
3d Br H H 87 40 75 7
3e Br Br H 89 40 79 8
3f NO2 H H 92 40 83 8
3g H H -CH3 88 30 78 7
3h F H -CH3 90 40 76 7
3i Cl H -CH3 86 40 77 8
3j Br H -CH3 85 40 80 8
3k H H -Bz 87 30 72 7
3l Cl H -Bz 91 40 76 7
3m Br H -Bz 88 40 75 8
3n H H 4-OCH3 Bz 84 30 70 6
3o Cl H 4-OCH3 Bz 85 30 74 8
3p Br H 4-OCH3 Bz 83 40 79 8
3q H H 4-Cl Bz 92 40 77 7
3r H H 4-COOCH3Bz 87 20 75 6
3s H H 4-CN Bz 86 40 79 8
3t H H -C6H5 83 30 80 7
3u H H -COCH3 87 30 73 7
3v Cl H -COCH3 85 40 75 8
3w H H -SO2C6H5 89 30 78 6