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. Author manuscript; available in PMC: 2012 Jun 17.
Published in final edited form as: J Org Chem. 2011 May 24;76(12):5092–5103. doi: 10.1021/jo200780x

Table 5.

Amidine Synthesis via Aza-Claisen Rearrangement.

entry ynamides aminesa amidine products yield [%]b
1 graphic file with name nihms296704t58.jpg 8b graphic file with name nihms296704t59.jpg graphic file with name nihms296704t60.jpg 56 94
2 graphic file with name nihms296704t61.jpg 8d graphic file with name nihms296704t62.jpg 57 58
3 graphic file with name nihms296704t63.jpg 8k graphic file with name nihms296704t64.jpg 58 77
4 graphic file with name nihms296704t65.jpg 8a graphic file with name nihms296704t66.jpg graphic file with name nihms296704t67.jpg 59 ≥95
5 graphic file with name nihms296704t68.jpg 8f graphic file with name nihms296704t69.jpg graphic file with name nihms296704t70.jpg 60 93
a

All reactions utilized 3.0 equiv of the amine and were run in toluene [concn = 0.05 M] at 110 °C over 24 h except it was 48 h for entry 4.

b

Isolated yields.