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. Author manuscript; available in PMC: 2012 Sep 1.
Published in final edited form as: Synthesis (Stuttg). 2011 Sep 1;2011(17):2743–2750. doi: 10.1055/s-0030-1260112

Table 1.

Optimization of One-Pot Elimination and Double Aza-Michael Reactiona

graphic file with name nihms311382t1.jpg
Entry Base Temp, time Solvent Yield (%)b
1 Cs2CO3 (1 equiv) 40 °C, 12 h MeCN 50
2 Cs2CO3 (1 equiv) 40 °C, 12 h CH2Cl2 44
3 Cs2CO3 (1 equiv) 40 °C, 12 h MeOH   0
4 Cs2CO3 (1 equiv) 60 °C, 12 h MeCN 43
5 Cs2CO3 (2 equiv) 60 °C, 12 h MeCN 32
6 Cs2CO3 (1 equiv) 40 °C, 12 h DMF 42
7 DBU (0.5 equiv) r.t., 12 h MeCN 23
8 DBU (0.1 equiv) 40 °C, 1 h DMF 30
9 DBU (0.1 equiv) r.t., 12 h MeOH 69
10 DBU (0.1 equiv) 40 °C, 1 h MeOH 75
a

A solution of compound 3a (1 equiv) and cyclopentylamine (1.1 equiv) in solvent (0.1 M) was added base and stirred at the indicated temperature and time.

b

Isolated yields following silica gel chromatography.