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. 2024 Apr 30;89(10):6915–6928. doi: 10.1021/acs.joc.4c00277

Table 4. Analysis of the Scope with 2-Coumaranones 3 and Chalcones 13.

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entry lactones chalcones Ar Ar′ time (h) yield (%)a d.rb
1 3a, R = H 13a Ph Ph 4 15a, 81 64/36
2 3a, H 13b 4-ClC6H4 Ph 5.5 15b, 83 53/47
3 3a, H 13f 4-MeOC6H4 Ph 5 15c, 87 54/46
4 3b, 5-OAc 13a Ph Ph 2.5 15d, 89 59/41
5 3a, H 13i Ph 4-MeOC6H4 5 15e, 83 62/38
6 3a, H 13d 2-ClC6H4 Ph 8.5 15f, 81 54/46
7 3a, H 13e 4-FC6H4 Ph 6.5 15g, 79 64/36
8c 3c, 5-Cl 13a Ph Ph 36 15h, 75 63/37
9d 3d, 5-NO2 13a Ph Ph 24 -e -
10d 3d, 5-NO2 13f 4-MeOC6H4 Ph 40 -e -
a

Isolated yield.

b

Determined by 1H NMR on the crude material.

c

Reaction temperature at 50 °C.

d

Reaction temperature at 80 °C.

e

Starting materials recovered.