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. Author manuscript; available in PMC: 2013 Apr 1.
Published in final edited form as: Tetrahedron. 2012 Feb 9;68(13):2819–2826. doi: 10.1016/j.tet.2012.02.002

Table 4.

Synthesis of benzonaphthyridinones and a dibenzonaphthyridinonea

graphic file with name nihms356273t23.jpg

Entry Aryne
precursor
Amine Product Yieldb (%)
1 graphic file with name nihms356273t24.jpg graphic file with name nihms356273t25.jpg graphic file with name nihms356273t26.jpg 56
2 graphic file with name nihms356273t27.jpg graphic file with name nihms356273t28.jpg 48
3 graphic file with name nihms356273t29.jpg graphic file with name nihms356273t30.jpg 53
4 graphic file with name nihms356273t31.jpg graphic file with name nihms356273t32.jpg 52
5 graphic file with name nihms356273t33.jpg graphic file with name nihms356273t34.jpg 48
6 graphic file with name nihms356273t35.jpg graphic file with name nihms356273t36.jpg 66
7 graphic file with name nihms356273t37.jpg graphic file with name nihms356273t38.jpg 72
8 graphic file with name nihms356273t39.jpg graphic file with name nihms356273t40.jpg 50
9 graphic file with name nihms356273t41.jpg graphic file with name nihms356273t42.jpg graphic file with name nihms356273t43.jpg 32
a

All reactions were carried out on a 0.25 mmol scale with 2 equiv of CsF at room temperature. A solution of 1 in 4 mL of MeCN (solution A) and a solution of 4 and sF in 4 mL of MeCN (solution B) were prepared separately. Solution A was slowly added to solution B with a syringe pump over 8 h, the resulting solution was stirred for an additional 16 h.

b

Isolated yield.