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. Author manuscript; available in PMC: 2017 Feb 19.
Published in final edited form as: Org Lett. 2016 Jan 19;18(4):631–633. doi: 10.1021/acs.orglett.5b03529

Table 1.

Evaluation of Reaction Conditionsa

graphic file with name nihms797531u2.jpg
entry solvent
(molarity)		 additive
(equiv)		 time
[h]		 yield 1a
(%)
1 PhMe (0.1) – 36 trace
2 PhMe (0.1) AcOH (0.2) 48 6
3 PhMe (0.1) AcOH (1) 48 28
4 PhMe (0.1) AcOH (5) 20 73
5 PhMe (0.1) AcOH (10) 20 52
6 xylenes (0.1) AcOH (5) 20 53
7 n-BuOH (0.1) AcOH (5) 20 55
8b DMF (0.1) AcOH (5) 18 52
9 PhMe (0.1) 2-EHA (5) 20 32
10 PhMe (0.1) BzOH (5) 20 63
11 PhMe (0.25) AcOH (5) 18 89
12 PhMe (0.5) AcOH (5) 15 75
13c PhMe (0.25) AcOH (5) 20 53
14d PhMe (0.25) AcOH (5) 20 85
a

Reactions were performed with 0.5 mmol of cyclohexylisocyanide. Yields are isolated yields of chromatographically purified compounds.

b

Reaction was performed at 135 °C.

c

With 3 equiv of pyrrolidine.

d

With 10 equiv of H2O.