Table 1: Synthesis of the [3-(9H-purin-9-ylmethyl)-4,5-dihydroisoxazol-5-yl]methoxy-2H-chromen-2-ones 4a-o.

Entry Oxime Alkenyloxycoumarin Product (Yield %)
1 2a 3a 4a (68)
2 2b 3a 4b (68)
3 2a 3b 4c (66)
4 2b 3b 4d (71)
5 2c 3b 4e (69)
6 2a 3c 4f (73)
7 2b 3c 4g (70)
8 2a 3d 4h (64)
9 2b 3d 4i (65)
10 2c 3d 4j (67)
11 2a 3e 4k (71)*, 1a (17%)
12 2b 3e 4l (68)*, 1b (14%)
13 2c 3e 4m (65)*, 1c (14%)
14 2a 3f 4n (65)*, 1a (15%)
15 2b 3f 4o (67)*, 1b (12%)

* By using PIDA, TFA and not NCS, Et3N.