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. Author manuscript; available in PMC: 2013 Feb 8.
Published in final edited form as: Tetrahedron Lett. 2012 Feb 8;53(6):612–615. doi: 10.1016/j.tetlet.2011.11.110

Table 2.

Preparation of benzisoxazolo[2,3-a]pyridinium tetrafluoroborates (1)a

graphic file with name nihms341497u2.jpg
Entry Acetanilide (4) Product (1) % Yieldb
1 4a graphic file with name nihms341497t17.jpg
1a
72
2 4b graphic file with name nihms341497t18.jpg
1b
77
3 4c graphic file with name nihms341497t19.jpg
1c
83
4 4d graphic file with name nihms341497t20.jpg
1d
79
5 4e graphic file with name nihms341497t21.jpg
1e
80
6 4f graphic file with name nihms341497t22.jpg
1f
71
7 4g graphic file with name nihms341497t23.jpg
1g
76
8 4h graphic file with name nihms341497t24.jpg
1h
74
a

Hydrolysis: 4 (1.0 mmol), HBF4 (50% aqueous solution, 1.2 mmol), water (1 mL), were refluxed until hydrolysis was complete. Diazotization/cyclization: the preceding mixture was evaporated in vacuo and dissolved in CH3CN (8 mL). tBuONO (1.2 mmol) was added. Mixture was stirred 1 hr at RT, then heated to reflux.

b

Isolated yields; average of at least 2 runs.