1390
D. R. Merchan Arenas et al. / Tetrahedron Letters 52 (2011) 1388–1391
R4
R4
R3
R2
NH2
O
O
O
H
N
R1
9a-g
R3
+
O
O
10
R2
.
R1
10 % BF3 OEt2
10 % KOH/Alumina
OCH3
MeCN/60 ºC
6-10 h
OCH3
OCH3
8
OH
7
OH
OH 11a-g
Clove bud essential oil
60.5 % Eugenol
Modified essential oil
with trans/cis -isoeugenol
40-70 %
Scheme 3. Synthesis of new heterolignan-like THQs 11a–g.
Table 3
Comparative physicochemical parameters of heterolignan-like THQs
Compd 11.
R1
R2
R3
R4
Mp (°C)
Yielda (%)
40 (35)b
Reaction time (h)
b
a
b
c
d
e
f
H
OH
H
H
H
H
H
H
OMe
OH
OMe
OMe
H
H
H
H
H
H
H
H
OMe
220–221
238–239
244–245
258–260
205–206
212–213
209–210
10 (7)
b
b
55 (55)
47 (40)
45 (40)
8 (6)
8 (7)
b
b
OH
OH
OMe
OMe
OMe
b
b
6 (4)
50
58
64
9
9
9
H
H
g
a
Isolated yield after column chromatographic purification.
Isolated yield for the synthesis with transformed EO and carry out in PEG 400.
b
Acknowledgments
O
O
NH2
O
O
+
HO
O
N
O
O
This work was supported by Instituto Colombiano para el
Desarrollo de la Ciencia y la Tecnología ‘Francisco José de Caldas’
(COLCIENCIAS-CENIVAM, contract no. 432-2004). DRMA thanks
COLCIENCIAS for the fellowship.
12
10
10 % BF3.OEt2
10 % KOH/Alumina
Solvent/60
°C
OCH3
OCH3
OCH3
13
7
8
OH
OH
OH
Supplementary data
Clove bud essential oil
60.5 % Eugenol
70 % (MeCN, 10 h)
50 % (PEG 400, 5 h)
Modified essential oil
with trans/cis- isoeugenol
Supplementary data associated with this article can be found, in
Scheme 4. Synthesis of new heterolignan-like THQ 13.
References and notes
Encouraged by the remarkable results obtained with the above
reaction conditions, and in order to show the robustness and scope
of this new protocol, we used phtalaldehydic acid 12 in our
scheme. This allowed us to construct a new pharmacologically
interesting isoindolo[2,1-a]quinolin-11(5H)-one derivative 13
(Scheme 4), which is formed in good yield via an intramolecular
condensation (dehydration) of the generated NH-tetrahydroquino-
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