Synthesis of 2-aminopyran derivatives and 3-arylpropionitrile derivatives catalyzed by KF/Al2O3

Article abstract of DOI:10.1081/SCC-120030692

A series of 2-cyano-3-aryl-3-(3,4-dihydro-1(2H)-naphthalene-one-2-yl) propionitrile derivatives and 2-aminopyran derivatives were synthesized by the KF-Al₂O₃-catalyzed reaction of malononitrile with 2-arylmethylidene-3,4-dihydro-1(2H

Full text of DOI:10.1081/SCC-120030692

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Synthesis of 2‐Aminopyran Derivatives and
3‐Arylpropionitrile Derivatives Catalyzed by KF/Al2O3
Xiang‐shan Wang a , Da‐qing Shi a , Ya Du a , Yan Zhou a & Shu‐jiang Tu a
a Department of Chemistry , Xuzhou Normal University , Xuzhou Jiangsu, 221116, China
Published online: 21 Aug 2006.
To cite this article: Xiang‐shan Wang , Da‐qing Shi , Ya Du , Yan Zhou & Shu‐jiang Tu (2004) Synthesis of 2‐Aminopyran
Derivatives and 3‐Arylpropionitrile Derivatives Catalyzed by KF/Al2O3 , Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 34:8, 1425-1432, DOI: 10.1081/SCC-120030692
To link to this article: http://dx.doi.org/10.1081/SCC-120030692
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SYNTHETIC COMMUNICATIONSw
Vol. 34, No. 8, pp. 1425–1432, 2004
Synthesis of 2-Aminopyran Derivatives and
3-Arylpropionitrile Derivatives
Catalyzed by KF/Al2O3
*
Xiang-shan Wang, Da-qing Shi, Ya Du,
Yan Zhou, and Shu-jiang Tu
Department of Chemistry, Xuzhou Normal University,
Xuzhou Jiangsu, China
ABSTRACT
A series of 2-cyano-3-aryl-3-(3,4-dihydro-1(2H)-naphthalene-one-2-yl)
propionitrile derivatives and 2-aminopyran derivatives were synthesized
by the KF-Al2O3-catalyzed reaction of malononitrile with 2-arylmethyl-
idene-3,4-dihydro-1(2H)-naphthalenone, 2,6-biarylmethylidene cyclo-
hexanone, or 2,5-biarylmethylidene cyclopenanone in DMF at room
temperature. The structure of the later was confirmed by x-ray analysis.
Key Words: Propionitrile; 2-Aminopyran; KF-Al2O3; Synthesis.
*
Correspondence: Xiang-shan Wang, Department of Chemistry, Xuzhou Normal
University, Xuzhou Jiangsu 221116, China; E-mail: xswang1974@yahoo.com.
1425
DOI: 10.1081/SCC-120030692
0039-7911 (Print); 1532-2432 (Online)
www.dekker.com
Copyright # 2004 by Marcel Dekker, Inc.

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Wang et al.
INTRODUCTION
Among a large group of plant products, designated as flavonoids, various
dihydrochalcone derivations have been reported to possess antimicrobial, anti-
viral, and physiological activities.[1] Uvaritin, a dihydrochalcone from Uvaria
acuminata has an antitumor activity.[2] Some dihydrochalcones have also been
found to be active against plant pathogens.[1] In addition, 2-aminochromene is
an important class of compounds found as the main compounds of many natu-
rally occurring products employed as cosmetics and pigments and utilized as
potential biodegradable agrochemicals.[3] The utility of fluoride salts as poten-
tial base in a variety of synthetic reactions has been recognized in recent
years.[4] Especially, alumina coated with potassium fluoride (KF-alumina)
as a catalyst resulting in higher selectivity, milder reaction conditions and
easier work-up, has been reported as a useful catalyst for many reactions.[5]
Herein we report the synthesis of 3-arylpropionitrile derivatives and 2-amino-
pyran derivatives catalyzed by KF/Al2O3.
When2-arylmethylidene-3,4-dihydro-1(2H)-naphthalenone(1)andmalono-
nitrile (2) were treated with KF-alumina in DMF at room temperature, the
desired 2-cyano-3-aryl-3-(3,4-dihydro-1(2H)-naphthaleneone-2-yl) propioni-
trile derivatives (3) were obtained in good yields (73–93%) (Table 1). But
it is interesting that the 2-aminopyran derivatives (5) were obtained, which
were not the expected simple addition products, when 2,6-biarylmethylidene
cyclohexanone or 2,5-biarylmethylidene cyclopenanone (4), malononitrile
(2), and KF/Al2O3 were treated in DMF, though the reaction was conducted
at room temperature (Sch. 1).
The structure of 5a was confirmed by x-ray analysis,a and the crystal
structure of 5a was shown in Fig. 1. X-ray reveals that the pyran ring adopts
a boat conformation: the atoms C(2), C(3), C(10), and C(9) are coplanar, while
˚
the atoms O and C(16) are away from the plane by 20.1226 and 20.1687 A.
The dihedral angles between the plane and the phenyl ring [C(1)–C(6)],
phenyl ring [C(17)–C(22)] are 33.578 and 86.088, respectively. In another
six-membered ring [C(8)–C(13)], the atoms C(8), C(9), C(11), C(12), and
C(13) are on one plane, while the atom C(10) is away from the plane
˚
by 0.6418 A, indicating that the ring adapts a half-chair conformation. The
aX-ray crystallography for 5a: Empirical formula C22H18Cl2N2O, FW ¼ 409.29,
˚
˚
T ¼ 296(2) K, monoclinic, space group P2(1)/n, a ¼ 13.582(2) A, b ¼ 8.974(1) A,
3
˚
˚
c ¼ 16.960(2) A, a ¼ 908, b ¼103.34(1)8, g ¼ 908, V ¼ 2011.4(4) A , Z ¼ 4,
Dc ¼ 1.352 mg m23
,
g(MoKa) ¼ 0.71073 A, m ¼ 0.339 mm21
,
F(000) ¼ 848.
˚
1.748 , u , 25.008, R ¼ 0.0361, wR ¼ 0.0790. S ¼ 0.876, largest diff. peak and
23
˚
hole: 0.138 and 20.156 e A
.

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1427
Table 1. The yields of the products 4 and 5.
Entry
Ar
C6H5
C6H5
R
Yield (%) Entry
Ar
n
Yield (%)
3a
3b
3c
3d
3e
3f
H
83
93
76
91
73
80
90
5a
5b
5c
5d
5e
5f
2-ClC6H4
C6H5
1
1
1
1
0
0
0
82
81
76
80
68
90
73
CH3
H
4-CH3C6H4
4-CH3C6H4
4-ClC6H4
2,4-Cl2C6H3
2-ClC6H4
4-CH3C6H4
2,4-Cl2C6H3
2,4-Cl2C6H3
C6H5
CH3
H
H
3g
H
5g
2-ClC6H4
Scheme 1.
Figure 1. Structure of the compound 5a.

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Wang et al.
dihedral angles between the plane and the phenyl ring [C(1)–C(6)], phenyl
ring [C(17)–C(22)] are 38.848 and 91.238, respectively.
EXPERIMENTAL
Melting points were determined in open capillaries and are uncorrected.
1
IR spectra were recorded on a TENSOR 27 spectrometer in KBr. H NMR
spectra were obtained for solutions in DMSO-d6 or CDCl3 with Me4Si as
internal standard using an Inova-400 spectrometer. Elemental analyses were
carried out using Carlo Erba 1110 analyzer. X-ray diffraction was measured
on a Siemens P4 diffractometer.
General Procedure
A dry 50-mL flask was charged with 2-arylmethylidene-3,4-dihydro-
1(2H)-naphthalenone (1) (5 mmol) or 2,6-biarylmethylidene cyclohexanone
or 2,5-biarylmethylidene cyclopenanone (4) (5 mmol), malononitrile (2)
(5 mmol), KF-alumina (500 mg), and DMF (15 mL). The mixture was stirred
at room temperature for 10–14 hr. The solid was filtered off and washed with a
small amount of DMF, and the filtrate was poured into 200 mL water; the
yellow solid was filtered off and washed with water. The crude product was
purified by recrystallization from 95% EtOH to give 3 or 5.
3a. 83%, m.p. 144–1468C; IR (KBr, n, cm21): 2964, 2265, 1673, 1599,
1513, 1455, 1431, 1379, 1301, 1268, 1214, 1192, 1150, 1115, 942, 893, 812,
776, 738, 595, 538; 1H NMR (CDCl3) d: 1.71–2.18 (m, 2H, CH2), 2.91–3.16
(m, 2H, CH2), 3.25–3.30 (m, 1H, CH), 3.47 (dd, 1H, J ¼ 4.4 Hz, J0 ¼ 10 Hz,
CH), 5.65 (d, 1H, J ¼ 10.0 Hz, CH), 7.20 (d, 1H, J ¼ 7 Hz, ArH), 7.30–7.32
(m, 6H, ArH), 7.48 (m, 1H, ArH), 8.03 (d,1H, J ¼ 8 Hz, ArH); Elemental
analysis: found(%) C, 80.21, H, 5.30, N, 9.24; calcd. for C20H16N2O: C,
79.98, H, 5.37, N, 9.33.
3b. 93%, m.p. 140–1428C; IR (KBr, n, cm21): 2935, 2230, 1659, 1608,
1493, 1454, 1376, 1296, 1232, 1164, 1131, 1023, 941, 828, 759, 704, 648, 559;
1H NMR (CDCl3) d: 1.68–2.10 (m, 2H, CH2), 2.36 (s, 3H, CH3), 2.84–3.10
(m, 2H, CH2), 3.22–3.27 (m, 1H, CH), 3.45 (dd, 1H, J ¼ 4.4 Hz, J0 ¼ 10 Hz,
CH), 5.68 (d, 1H, J ¼ 10 Hz, CH), 6.99 (s, 1H, ArH), 7.13 (d, 1H, J ¼ 8.4 Hz,
ArH), 7.32–7.44 (m, 5H, ArH), 7.93 (d, 1H, J ¼ 8.4 Hz, ArH); Elemental
analysis: found (%) C, 80.48, H, 5.69, N, 8.87; calcd. for C21H18N2O: C,
80.23, H, 5.77, N, 8.91.
3c. 76%, m.p. 188–1898C; IR (KBr, n, cm21): 2945, 2240, 1681, 1598,
1494, 1454, 1371, 1297, 1228, 1157, 1019, 943, 789, 764, 726, 702, 646, 608;

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1H NMR (CDCl3) d: 1.72–2.11 (m, 2H, CH2), 2.29 (s, 3H, CH3), 2.90–3.14
(m, 2H, CH2), 3.23–3.28 (m, 1H, CH), 3.43 (dd, 1H, J ¼ 4.4 Hz, J0 ¼ 11 Hz,
CH), 5.64 (d, 1H, J ¼ 11 Hz, CH), 7.12 (d, 1H, J ¼ 7 Hz, ArH), 7.19–7.50
(m, 5H, ArH), 8.03 (d, 1H, J ¼ 7 Hz, ArH); Elemental analysis: found (%)
C, 80.36, H, 5.62, N, 8.73; calcd. for C21H18N2O: C, 80.23, H, 5.77, N, 8.91.
3d. 91%, m.p. 142–1448C; IR (KBr, n, cm21): 2935, 2231, 1671, 1607,
1512, 1454, 1379, 1298, 1269, 1231, 1190, 1133, 1018, 945, 810, 793, 718,
1
668, 597, 568; H NMR (CDCl3) d: 1.68–2.08 (m, 2H, CH2), 2.29 (s, 3H,
CH3), 2.35 (s, 3H, CH3), 2.83–3.09 (m, 2H, CH2), 3.19–3.24 (m, 1H, CH),
4.01 (dd, 1H, J ¼ 4.4 Hz, J0 ¼ 11Hz, CH), 5.66 (d, 1H, J ¼ 11 Hz, CH), 6.99–
7.29 (m, 6H, ArH), 7.92 (d, 1H, J ¼ 8.4 Hz, ArH); Elemental analysis: found
(%) C, 80.52, H, 6.09, N, 8.46; calcd. for C22H20N2O: C, 80.46, H, 6.14, N, 8.53.
3e. 73%, m.p. 151–1538C; IR (KBr, n, cm21): 2961, 2242, 1671, 1599,
1491, 1456, 1432, 1413, 1379, 1298, 1229, 1150, 1096, 1015, 942, 820, 795,
757, 733, 676, 593; 1H NMR (CDCl3) d: 1.69–2.11 (m, 2H, CH2), 2.93–3.17
(m, 2H, CH2), 3.25–3.31 (m, 1H, CH), 3.45 (dd, 1H, J ¼ 4.4 Hz, J0 ¼ 10 Hz,
CH), 5.64 (d, 1H, J ¼ 10 Hz, CH), 7.21 (d, 1H, J ¼ 7 Hz, ArH), 7.24–7.52
(m, 8H, ArH), 8.02 (d, 1H, J ¼ 7 Hz, ArH); Elemental analysis: found (%)
C, 71.89, H, 4.37, N, 8.36; calcd. for C20H15ClN2O: C, 71.75, H, 4.52, N, 8.37.
3f. 80%, m.p. 190–1928C; IR (KBr, n, cm21): 2926, 2251, 1671, 1599,
1476, 1456, 1433, 1383, 1305, 1296, 1232, 1152, 1106, 1050, 1019, 942,
884, 861, 813, 786, 767, 735, 663, 595, 564; 1H NMR (CDCl3) d: 1.60–2.30
(m, 2H, CH2), 2.94–3.16 (m, 2H, CH2), 3.22–3.38 (m, 1H, CH), 4.39 (dd,
1H, J ¼ 4.4 Hz, J0 ¼ 10 Hz, CH), 5.55 (d, 1H, J ¼ 10 Hz, CH), 7.21–7.51
(m, 6H, ArH), 8.03 (d, 1H, J ¼ 7 Hz, ArH); Elemental analysis: found (%)
C, 65.21, H, 3.80, N, 7.51; calcd. for C20H14Cl2N2O: C, 65.06, H, 3.82, N, 7.59.
3g. 90%, m.p. 182–1848C; IR (KBr, n, cm21): 2921, 2234, 1670, 1599,
1476, 1453, 1434, 1379, 1310, 1270, 1231, 1152, 1040, 941, 883, 795, 752,
1
736, 688, 611, 587; H NMR (CDCl3) d: 1.71–2.32 (m, 2H, CH2), 2.92–
3.15 (m, 2H, CH2), 3.32–3.38 (m, 1H, CH), 4.46 (dd, 1H, J ¼ 4.4 Hz,
J0 ¼ 11.4 Hz, CH), 5.65 (d, 1H, J ¼ 11.4 Hz, CH), 7.20–7.55 (m, 7H, ArH),
8.04 (d, 1H, J ¼ 7 Hz, ArH); Elemental analysis: found (%) C, 71.82, H,
4.48, N, 8.30; calcd. for C20H15ClN2O: C, 71.75, H, 4.52, N, 8.37.
1
5a. 82%, m.p. 237–2388C; H NMR (DMSO-d6, d, ppm): 1.46–1.54
(m, 2H, CH2), 1.69–2.10 (m, 2H, CH2), 2.33–2.45 (m, 2H, CH2), 4.57
(s, 1H, CH), 6.91 (s, 2H, NH2), 6.97 (s, 1H, CH), 7.28–7.51 (m, 8H, ArH);
IR (KBr, cm21): 3464, 3344, 2920, 2191, 1671, 1637, 1594, 1468, 1414,
1254, 1130, 1030, 859, 822, 747, 693; Elemental analysis: found (%) C,
67.58, H, 4.40, N, 6.88; calcd. for C23H18Cl2N2O: C, 67.49, H, 4.43, N, 6.84.
5b. 81%, m.p. 231–2338C (228–2308C);[6] 1H NMR (CDCl3, d, ppm):
1.61–1.63 (m, 2H, CH2), 1.93–2.04 (m, 2H, CH2), 2.57–2.75 (m, 2H,
CH2), 3.97 (s, 1H, CH), 4.52 (s, 2H, NH2), 6.88 (s, 1H, CH), 7.25–7.38

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Wang et al.
(m, 10H, ArH); IR (KBr, cm21): 3460, 3338, 3077, 2927, 2900, 2204, 1681,
1648, 1621, 1603, 1469, 1471, 1394, 1110, 980, 750, 707.
5c. 76%, m.p. 162–1638C; 1H NMR (CDCl3, d, ppm): 1.57–1.62 (m, 2H,
CH2), 1.95–1.98 (m, 2H, CH2), 2.34 (s, 3H, CH3), 2.36 (s, 3H, CH3), 2.55–2.74
(m, 2H, CH2), 3.93 (s, 1H, CH), 4.50 (s, 2H, NH2), 6.84 (s, 1H, CH), 7.12–7.22
(m, 8H, ArH); IR (KBr, cm21): 3426, 3340, 3025, 2949, 2850, 2192, 1669, 1657,
1643, 1600, 1507, 1418, 1263, 1142, 1047, 840; Elemental analysis: found (%) C,
81.58, H, 6.40, N, 7.88; calcd. for C25H24N2O: C, 81.49, H, 6.57, N, 7.60.
5d. 80%, m.p. 195–1968C; 1H NMR (CDCl3, d, ppm): 1.57–1.67 (m, 2H,
CH2), 1.84–2.12 (m, 2H, CH2), 2.38–2.64 (m, 2H, CH2), 4.62 (s, 2H, NH2),
4.67 (s, 1H, CH), 6.84 (s, 1H, CH), 7.18–7.44 (m, 6H, ArH); IR (KBr, cm21):
3436, 3325, 3025, 2929, 2196, 1672, 1633, 1605, 1513, 1401, 1266, 1126,
1050, 880, 813, 770; Elemental analysis: found (%) C, 57.58, H, 3.40, N,
5.88; calcd. for C23H16Cl4N2O: C, 57.77, H, 3.37, N, 5.86.
5e. 68%, m.p. 238–2398C; 1H NMR (CDCl3, d, ppm): 2.14–2.19 (m, 1H,
CH), 2.46–2.52 (m, 1H, CH), 2.70–2.84 (m, 2H, CH2), 4.77 (s, 2H, NH2),
4.90 (s, 1H, CH), 6.67 (s, 1H, CH), 7.21–7.42 (m, 6H, ArH); 3487, 3351,
3074, 2929, 2869, 2207, 1690, 1648, 1596, 1484, 1448, 1416, 1387, 1115,
1046, 870, 761; Elemental analysis: found (%) C, 56.85, H, 3.01, N, 6.18;
calcd. for C22H14Cl4N2O: C, 56.93, H, 3.04, N, 6.04.
5f. 90%, m.p. 228–2308C; 1H NMR (CDCl3, d, ppm): 2.18–2.26 (m, 1H,
CH), 2.35–2.41 (m, 1H, CH), 2.86–2.91 (m, 2H, CH2), 4.27 (s, 1H, CH), 4.64
(s, 2H, NH2), 6.44 (s, 1H, CH), 7.20–7.39 (m, 10H, ArH); IR (KBr, cm21):
3325, 3177, 3009, 2937, 2837, 2195, 1657, 1604, 1521, 1394, 1274, 1142,
1058, 1022, 751, 695; Elemental analysis: found (%) C, 81.17, H, 5.58, N,
8.71; calcd. for C22H18N2O: C, 80.96, H, 5.56, N, 8.58.
5g. 73%, m.p. 213–2158C; 1H NMR (CDCl3, d, ppm): 2.14–2.20 (m, 1H,
CH), 2.46–2.52 (m, 1H, CH), 2.73–2.87 (m, 2H, CH2), 4.76 (s, 2H, NH2),
4.95 (s, 1H, CH), 6.74 (s, 1H, CH), 7.13–7.48 (m, 8H, ArH); IR (KBr,
cm21): 3467, 3331, 3030, 2934, 2197, 1655, 1595, 1469, 1458, 1378, 1278,
1182, 1078, 697; Elemental analysis: found (%) C, 66.69, H, 4.30, N, 6.88;
calcd. for C22H16Cl2N2O: C, 66.85, H, 4.08, N, 7.09.
ACKNOWLEDGMENT
We are grateful to the Foundation of the “Surpassing Project” of Jiangsu
Province for financial support.
REFERENCES
1. (a) Lespagnol, A.; Lespagnoa, C.; Lesieur, D.; Cazin, J.C.; Cazin, M.;
Beerens, H.; Romond, C. Analgesic, antiimflammatory and antimicrobial

ORDER
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Derivatives of 2-Aminopyran and 3-Arylpropionitrile
1431
activities of chalcones and dihydrochalcones derived from salicylic
acid. Chim. Ther. 1972, 7, 365; (b) Chowdhury, A.; Mukherjee, N.;
Adityachaudhury, N. Sensitivity of some plant pathogenic fungi
towards plant metabolites. Antifungal activity of some chalcones,
dihydrochalcones and flavanones. Experientia 1974, 30, 1022;
(c) Hodson, H.F.; Selway, J.W.T.; Leaver, C.M. Substituted diaryl
compounds and pharmaceutical compositions containing them. Eur. Pat.
Appl. 1981, 28, 305; (d) Bauer, D.J.; Selwey, J.W.T.; Batchelor, J.F.;
Tisdale, M.; Caldwell, I.C.; Young, D.A.B. 40,6-dichloroflavan
(BW683C), a new antirhinovirus compound. Nature 1981, 292, 369;
(e) Hromatka, O. Nitrochroman. US Pat. 2,343,773, 1974; (f) Soulie, P.;
Chiche, P.; Carlothi, J.; Baillet, J. Tentative use of 3-methylchromane
in angina pectoris. Presse Med. 1954, 62, 847; (g) Witiak, D.T.;
Heilman, W.P.; Sankarappa, S.K.; Cavestri, R.C.; Newman, H.A.I.
Synthesis of ethyl 6-substituted chroman and chromone-2-carboxylates.
Comparative structure–activity study employing the 6-phenyl
analogs in the triton hyperlipidemic rat model. J. Med. Chem. 1975, 18,
934.
2. Cole, J.R.; Torrance, S.J.; Weidhopf, R.M.; Arora, S.K.; Bates, R.B.
Uvaretin, a new antitumor agent from Uvaria acuminata (annonaceae).
J. Org. Chem. 1976, 41, 1852.
3. (a) Morinaka, Y.; Takahashi, K. Quinolopyran-4-one-2carboxylic acid
derivatives. Japan Kokai. 1977, 17, 498; (b) Witte, E.C.; Neuert, P.;
Roesch, A. 7-(Piperazinylpropoxy)-2H-1-benzopyran-2-ones. Ger.
Offen. DE 3,427,985; 1986; (c) Hafez, E.A.; Elnagdi, M.H.;
Elagamey, A.A.; El-Taweel, F.A. Nitriles in heterocyclic synthesis:
novel synthesis of benzo[c]courmarin and benzo[c]pyrano[3,2-c]
quinoline derivatives. Heterocycles 1987, 26, 903.
4. (a) Clark, J.H. Drifluor reagents: non-hydroscopic sources of the fluoride
ion. J. Chem. Soc. Chem. Commun. 1978 (18), 789; (b) Clark, J.H.;
Miller, J.M. Hydrogen bonding in organic synthesis. 3. Hydrogen bond
assisted
reactions
of
cyclic
organic
hydrogen
bond
electron acceptors with halogenoalkanes in the presence of potassium
fluoride. J. Am. Chem. Soc. 1977, 99, 498; (c) Ando, T.; Yamawak, J.
Potassium fluoride on celite. A versatile reagent for C-, N-, O-, and
S-alkylations. Chem. Lett. 1979 (1), 45.
5. (a) Wang, X.S.; Shi, D.Q.; Tu, S.J. Synthesis of 3-aryl-3-(5,5-dimenthyl-
3-hydroxylcyclohex-2-ene-1-one-2-yl)propionamide derivatives cata-
lyzed by KF-Al203. Chin. J. Org. Chem. 2002, 22 (11), 909 (in Chinese);
(b) Wang, X.S.; Shi, D.Q.; Tu, S.J. A convenient synthesis of
5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyran derivatives catalyzed by
KF-alumina. Synth. Commun. 2003, 33 (1), 119; (c) Wang, X.S.;

ORDER
REPRINTS
1432
Wang et al.
Shi, D.Q.; Tu, S.J. Synthesis of 3,4-dihydro-2H-pyrano[3,2-h]quinoline
derivatives catalyzed by KF-Al203. Chin. J. Org. Chem. 2003, 23, 203
(in Chinese).
6. Zhou, J.F. One-step synthesis pyridine and 4H-pyran derivatives from
bisarylidenecyclohexanone and malonontrile under microwave
irradiation. Synth. Commun. 2003, 33 (1), 99.
Received in Japan August 18, 2003

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