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12 2 100 °C - -
13 2 100 °C Cu Powder (200 mesh) Traces
14 e - f 25 °C Cu(Oac)2, 5 24
a
All reactions were run on a 0.7 mmol scale of 3, applying phenyl acetylene (1.2
equiv) in ethanol: water (4:1, 1 mL) under microwave irradiation. The mixture was
irradiated in a sealed tube (CEM Discover @ ) at a ceiling temperature of 100 o C and 35
W maximum power for the stipulated time. b isolated yields. c 1.0 equiv of
NH2NH2.H2O used. d 5.0 equiv of NH2NH2.H2O used. e reaction carried out at room
temperature. f time 24 h.
Table-1: Copper Catalyzed One-Pot protocol: Catalyst, equiv of hydrazine, reaction
time and Temperature Effects on the model reaction to obtain 2-AI-T scaffold a .
4.3 Results and Discussion
Encouraged by these findings, the scope of this protocol was further explored. An
array of hydroxy salts 3 (a-j) (Table-2) were reacted with various acetylene using our
optimized conditions. In most cases, the reactions proceeded well affording the one
pot product in good to excellent yield (Table-2)
R 2
N
1
+
N
Br
2
N
H
O
R 1
N 3
n
MeCN, 75 o C,
3 Hrs
R 3
N N
n
3
N
Br N
R OH
2 R1 Cu(OAc) 2 (5 mol. %)
MW. 100 o N2H4 C
3 {a-j}
2-5 min, 85-90 %
One-pot Microwave-assisted
R 2
R 1
N
N
H
NH
N
N R3 N
n
4 {a-v}