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. 2023 Jan 16;13(4):2365–2371. doi: 10.1039/d2ra07259a

Optimization of reaction conditionsa.

graphic file with name d2ra07259a-u3.jpg
S. no. Pd(OAc)2 PTSA (equiv.) Yieldsb (%)
1 10 mol% 0.75 60
2 10 mol% 1.0 56
3 10 mol% 0.25 69
4 15 mol% 0.25 46
5 7.5 mol% 0.25 69
6 5 mol% 0.25 74
7 3 mol% 0.25 70
8 5 mol% 0.25 64c
9 5 mol% 0.25 70d
10 5 mol% 0.25 61e
11 5 mol% 0.25 62f
12 5 mol% 0.25 84 g
13 5 mol% 0.25 65h
14 5 mol% 0.25 70i
a

Reagents and conditions: a mixture of 3-phenyl-2H-benzo[b][1,4]oxazin-2-one (1a, 1 equiv.), NBS (2a, 1.2 equiv.), Pd(OAc)2 and PTSA as indicated in the parenthesis were irradiated with microwave under indicated solvent at indicated temperature for given period of time in sealed reaction vial.

b

Isolated yields.

c

Reaction mixture was irradiated at 110 °C for 15 minutes.

d

Reaction mixture was irradiated at 90 °C for 30 minutes.

e

Reaction was irradiated at 80 °C for 30 minutes.

f

Reaction was irradiated at 100 °C for 25 minutes.

g

Reaction was irradiated at 100 °C for 15 minutes.

h

Reaction was irradiated at 100 °C for 10 minutes.

i

Reaction was carried out at 100 °C under conventional heating for 1 hour.