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. Author manuscript; available in PMC: 2019 Aug 9.
Published in final edited form as: J Org Chem. 2016 Apr 12;81(9):3924–3928. doi: 10.1021/acs.joc.6b00338

Table 4.

One-Pot Isoquinolino[3,4–b]quinoxaline (7a) Optimization Studies

graphic file with name nihms-1044829-t0005.jpg
entry M+CN− solvent conditionsa yieldb (%)
1 KCN DMF under N2/NaCl 15
2 KCN DMF under N2/18-crown-6 28
3 KCN DMF under N2/none 31
4 KCN MeCN under N2/none 0
5 NaCN DMF under N2/none 37
6 NaCN DMF open air/none 36
7 NaCN MeCN under N2/none 0
8 NaCN HMPA under N2/none 0
9 NaCN DMSO under N2/none 0
10 NaCN THF under N2/Bu4NCl tracec
a

Conditions: under N2 or open to the air/additive.

b

Overall yield.

c

Trace; determined by LCMS of the crude reaction.