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. 2021 Jan 8;11(4):2221–2225. doi: 10.1039/d0ra00686f

Reaction of β-bromo-β-nitrostyrene 1a with 1,3-diphenylthiourea 2a under different conditions.

graphic file with name d0ra00686f-u1.jpg
Entrya Base Solvent Temperature (°C) Time (h) Yield (%)
1 K2CO3 THF rt 24 62
2b K2CO3 THF 70 10 60
3 Et3N THF rt 24 72
4b Et3N THF 70 10 65
5 DBU THF rt 24 63
6b DBU THF 70 10 58
7 KHCO3 THF rt 24 55
8b KHCO3 THF 70 10 60
9 DIPEA THF rt 24 68
10 None THF rt 24 29
11c Et3N THF rt 24 64
12d Et3N THF rt 24 58
13e Et3N THF rt 24 17
14 Et3N CH2Cl2 rt 24 45
15 Et3N Toluene rt 24 42
16b Et3N Toluene 110 5 40
a

Reactions were performed with β-bromo-β-nitrostyrene 1a (0.10 mmol) and 1,3-diphenylthiourea 2a (0.11 mmol) with base (0.02 mmol) in the indicated solvent (2.0 mL) under atmospheric air.

b

β-Bromo-β-nitrostyrene was completely consumed.

c

Reaction was carried out with 0.04 mmol of base.

d

Reaction was carried out with 0.01 mmol of base.

e

Reaction was carried out with 0.1 mmol of base.