Chemistry Reference
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N,N-dimethyl-4-aminopyridine (DMAP), under vibrational ball-milling to
synthesize the corresponding amides (Scheme 1.11).
13
Jin et al. have reported an ecient solvent and catalyst-free aza-Michael
addition of chalcone to amine under the high-speed vibration ball-milling in
a short reaction time (Scheme 1.12).
14
In general, excellent yields were ob-
tained, eliminating the usual side reactions. It was also observed that the
yields of the corresponding products obtained using anilines were lower
compared to those using benzyl amine or piperidine.
O
O
DMAP (1.5 equiv.)
vibration ball-milling
(28 Hz)
10 min
O
R
2
R
2
NH
2
+
N
R
1
H
R
1
O
O
65-94%
Some selected examples:
O
O
H
H
N
N
N
N
65%
90%
OMe
O
OH
O
N
H
Me
N
H
N
N
HO
72%
77%
Scheme 1.11 C-N bond forming reaction of propargylamine with N-hydroxysucci-
nimidyl p-(phenylazo)benzoate under ball milling.
R
3
O
NH
O
HSVM, 30 H
z
Catalyst-free
25 min.
+
R
3
NH
2
R
1
R
1
R
2
R
2
47-99%
Some selected examples:
NH
O
NH
O
NH
O
Br
OCH
3
O
2
N
OCH
3
F
3
C
90%
90%
99%
Cl
H
3
C
H
3
CO
NH
O
NH
O
NH
O
N
O
OCH
3
59%
52%
47%
89%
NO
2
Scheme 1.12 Aza-Michael addition of different amines to chalcones under HSVM
conditions.
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