H. A. Dabbagh et al. / Tetrahedron Letters 47 (2006) 3929–3932
3931
H
Me
Me
Me
N N
N N
N
N
N N
N
N
N
N
O
O
O
O
N
N
CH
3
I
N
N
O
O
O
N
N
N
+
+
Excess
O
N
N
N
N
N
N
H
N
N
N
N
N
N
N
Me
1
Me
Me
1A
1B
1C
Scheme 3.
as new BIZOL ligands for the synthesis of novel
complexes.
white solid. The progress of the reaction was followed by
thin layer chromatography and when cyanate formation
was completed, sodium azide (0.13 g, 20 mmol) dissolved
in water–acetone (50:50) was added dropwise with stirring
at room temperature for 2 h and then at reflux for 5 h. The
reaction mixture was cooled to room temperature and
acidified with hydrochloric acid (5%) and then extracted
with diethyl ether (2 · 20 ml). Purification of the concen-
trated reaction mixture by silica gel chromatography
Acknowledgement
We would like to thank Isfahan University of Techno-
logy (IUT) for the financial support (Grant # 84/500/
9
143).
(
30:70 ethyl acetate–cyclohexane) afforded the products.
0
0
The first fraction was 1,1 -binaphthalene-2,2 -diol (0.8 g,
6
1
8
1% recovered), mp = 215–216 ꢁC. The next fraction
References and notes
. Butler, R. N. In Comprehensive Heterocyclic Chemistry;
was mono-tetrazolated binaphthol 2: 1-(2-(1H-tetrazole-5-
yloxy)naphthalen-1-yl)naphthalen-2-ol (0.40 g, 21% con-
version), mp = 172–174 ꢁC [for (+)-2, mp = 128–130 ꢁC
and for (ꢀ)-2, mp = 122–124 ꢁC]. IR (KBr): 3435, 3028,
2923, 2854, 2739, 2633, 2478, 1609, 1598, 1577, 1509, 1445,
1
Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.;
Pergamon: Oxford, UK, 1996; Vol. 4, p 621.
ꢀ
1416, 1239, 1205, 1108, 777 cm ; H NMR (DMSO-d ,
6
1 1
2
3
. Herr, R. J. Bioorg. Med. Chem. 2002, 10, 3379–3393.
. Upadhayaya, R. S.; Sinha, N.; Jain, S.; Kishore, N.;
Chandra, R.; Arora, S. K. Bioorg. Med. Chem. 2004, 12,
500 MHz): d 6.98 (1H, d, J = 8.4 Hz), 7.07 (1H, d,
J = 8.4 Hz), 7.20 (1H, t, J = 7.9 Hz), 7.28–7.35 (m, 2H),
7.50 (1H, t, J = 7.4 Hz), 7.56 (1H, d, J = 9.1 Hz), 7.68
(1H, d, J = 9.0 Hz), 7.92 (1H, d, J = 8.0 Hz), 8.08 (2H, t,
2
225–2238.
4
5
. Tompa, A. S. Thermochim. Acta 1984, 80, 367–377.
. (a)For monographs, see: Houben-Weyl Stereoselective
Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J.,
Schaumann, E., Eds.; Georg Thieme: Stuttgart, 1996; (b)
Handbook of Reagents for Organic Synthesis: Chiral
Reagents for Asymmetric Synthesis; Paquette, L. A., Ed.;
John Wiley & Sons: Chichester, 2003; (c) Chen, Y.; Yekta,
S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155–3212; (d)
Kocovsky, P.; Vyskocil, S.; Smrcina, M. Chem. Rev. 2003,
1
3
J = 8.3 Hz), 8.15 (1H, d, J = 9.0 Hz); C NMR (DMSO-
6
d , 125 MHz): d 114.2, 116.2, 120.3, 123.7, 123.9, 124.6,
125.9, 126.0, 126.2, 127.5, 128.5, 128.7, 129.0, 130.2, 130.8,
131.7, 133.4, 133.6, 149.9, 155.2, 161.6; MS (EI), m/z =
+
354 (M ), 339, 326, 311, 296, 287, 267, 252, 246, 239,
14 4 2
212, 155, 127, 115; Anal. Calcd for C21H N O : C, 71.2,
2
5
H, 4.0, N, 15.8. Found: 71.3, 3.8, 14.0. ½aꢁ +43.3 and
D
ꢀ42.7 (acetone, c 0.5) for (R)-2 and (S)-2, respectively.
The final fraction was 5-(1-(2-(1H-tetrazole-5-yloxy)-
naphthalen-1-yl)naphthalen-2-yloxy)-1H-tetrazole 1 (0.7 g,
18% conversion), mp = 238–240 ꢁC [for (+)-1, mp = 178–
180 ꢁC and for (ꢀ)-1, mp = 186–188 ꢁC]; IR (KBr): 3062,
1
03, 3213–3245.
. Foubelo, F.; Moreno, B.; Yus, M. Tetrahedron Lett. 2004,
5, 8983–8986.
. (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochem-
istry of Organic Compounds; John Wiley & Sons: New
York, 1994, p 1142; (b) Di Bari, L.; Pescitelli, G.;
Salvadori, P. J. Am. Chem. Soc. 1999, 121, 7998–8004.
. Pu, L. Chem. Rev. 1998, 98, 2405–2494.
6
7
4
ꢀ1
1
2910, 2730, 2642, 1578, 1505, 1206, 1075 cm
;
H
NMR(DMSO-d , 500 MHz): d 7.85 (2H, d, J = 8.4 Hz),
6
7.35 (2H, t, J = 7.7 Hz), 7.50 (2H, t, J = 7.3 Hz), 7.62 (2H,
d, J = 9.0 Hz), 8.00 (2H, d, J = 8.0 Hz), 8.20 (2H, d,
8
9
1
3
. Dabbagh, H. A.; Lwowski, W. J. Org. Chem. 2000, 65,
J = 9.0 Hz); C NMR (DMSO-d , 125 MHz): d 115.0,
6
7
284–7290.
0. Dabbagh, H. A.; Mansoori, Y. Russ. J. Org. Chem. 2001,
7, 1771–1781.
1. Dabbagh, H. A.; Karimzadeh, R. Molecules 2002, 7, 189–
99.
2. Dabbagh, H. A.; Gaelee, S. J. Org. Chem. 1996, 61, 3439–
445.
119.1, 125.8, 126.9, 127.5, 127.7, 130.1, 130.7, 133.7, 151.8,
166.5; MS (EI), m/z = 422 (M ), 394, 382, 365, 354, 337,
309, 297, 286, 268, 239, 226, 125, 119; Anal. Calcd for
+
1
1
1
1
1
3
C H N O : C, 62.6, H, 3.4, N, 26.5. Found: C. 62.8, H,
22 14 8 2
25
1
3.8, N, 24.5. ½aꢁ +29.9 and ꢀ28.9 (acetone, c 0.5) for
D
(R)-1 and (S)-1, respectively.
1
9
3
15. 1-(2-Methoxynaphthalen-1-yl)naphthalene-2-ol (3): To a
solution of 1-(2-hydroxynaphthalene-1-yl)naphthalene-2-ol
(0.57 g, 20 mmol) in acetone was added potassium carbon-
ate (0.35 g, 25 mmol). After stirring for 10 min, methyl
iodide (0.2 ml, 30 mmol) in acetone was added dropwise at
room temperature and the mixture stirred for 30 h. The
mixture was filtered and washed with acetone three times.
Acetone was evaporated under reduced pressure and the
racemic mixture was purified by recrystallization from
carbon tetrachloride to give a 50% yield of 3. The melting
3. Dabbagh, H. A.; Mansoori, Y.; Jafari, M.; Rostami, M. J.
Chem. Res. (S) 2000, 442–445.
4. A typical method for the preparation of compounds 1 and 2:
0
To a solution of a racemic mixture of 1,1 -binaphthalene-
2
ature was added cyanogen bromide (1.75 g, 15 mmol).
0
,2 -diol (1.43 g, 5 mmol) in acetone at ice-bath temper-
When the temperature reached below 5 ꢁC, triethylamine
(
2.75 ml, 20 mmol) was added dropwise. After a few
minutes tetraethylammonium bromide precipitated as a