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. 2021 Nov 18;86(23):16425–16433. doi: 10.1021/acs.joc.1c01785

Table 2. Aza-Prins Reaction of 1 with Isatin Derivatives.

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entry isatin time (h) product yield (%)
1 R = H (5a) 22 6a 70
2 R = 5-NO2 (5b) 13 6b 69
3 R = 5-CF3O (5c) 8 6c 63
4 R = 5-F (5d) 46 6d 67
5 R = 5-Br (5e) 16 6e 74
6 R = 5-MeO (5f) 40 6f 33
7 R = 1-Me (5g) 40 6g 82
8a R = 6-Cl (5h) 22 6h 50
9 R = 7-Cl (5i) 19 6i 69
10a R = 4-Cl (5j) 72 6j 0
11 R = 6-CF3 (5k) 17 6k 66
12 R = 6-CH3O (5l) 43 6l 3.4
a

4 M HCl/dioxane was used as the acid.