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. Author manuscript; available in PMC: 2019 Aug 17.
Published in final edited form as: J Org Chem. 2018 Jun 27;83(16):9522–9529. doi: 10.1021/acs.joc.8b01249

Table 1.

Reaction Parameters for Annulations to Azolotriazines 6a

graphic file with name nihms-979964-f0007.jpg

entry imine variation Yield %b
1 1a none 75 (73)c
2 1a [Cp*RhCl2]2, AgSbF6d 60
3 1a [Cp*RhCl2]2(5 mol %) 8
4 1a no Rh 0
5 1a no PivOH 12
6 1a no NaOAc 16
7 1a NaOAc (1 equiv) 79
8 1a 100 oC 70
9 1a 0.2 M 46
10 1a toluene as solvent 11
11 1a DCE as solvent 9
12 1a MeCN as solvent 25
13 1a [Cp*IrCl2]2, AgSbF6d 10
14 1a [Cp*Co(MeCN)3](SbF6)2 0
15 1b none 53 (55)e
16 1b NaOAc (1 equiv) 37
17 1b 100 °C 43
a

Conditions: 1 (0.10 mmol), 4a (0.15 mmol), 0.1 M, 16 h.

b

Yield determined by 1H-NMR relative to 1,3,5-trimethoxybenzene as external standard.

c

Isolated yield of a 0.30 mmol scale (see Scheme 2).

d

[Cp*MCl2]2 (5 mol %) and AgSbF6 (20 mol %).

e

Isolated yield of a 0.30 mmol scale (see Scheme 3).