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DOI: 10.1055/s-0031-1289906
[MeC(OH)2]+ClO4 -: A New Efficient Organocatalyst for the Preparation of 1-Amido- and 1-Carbamato-alkyl Naphthols
Publication History
Publication Date:
23 November 2011 (online)
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Abstract
[MeC(OH)2]+ClO4 - as a super acidic ionic liquid is found to be a new and highly efficient catalyst in the synthesis of amidoalkyl naphthols via three-component condensation of β-naphthol and aldehydes with nitriles, amides, or carbamates.
Key words
multicomponent reactions - amidoalkyl naphthols - ionic liquids - super acids
- 1
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References and Notes
Tamaddon, F.; Tavakoli, F. manuscript submitted for publication.
33
General Procedure
for the [MeC(OH)
2
]
+
ClO
4
-
-Catalyzed
Synthesis of Amidoalkyl Naphthols
A mixture of an
aldehyde (1 mmol), β-naphthol (1 mmol) with amide, nitrile,
urea, or carbamate (1 mmol) in the presence of [MeC(OH)2]+ClO4
- (1
mol%) was stirred in EtOAc (1 mL) at r.t. (or at 80 ˚C
under solvent-free conditions) for the given times. After completion
of the reaction (TLC monitoring), H2O was added, and
the precipitate was filtered off to give the corresponding amidoalkyl
naphthols. Most of the products were known and characterized by
comparison of their melting points and spectral data with those
reported in the literature without further purification. In some
cases the products were recrystallized from EtOH-H2O
(60:40).
Selected Characterization
Data
N
-[(2-Hydroxynaphthalen-1-yl)(phenyl)methyl]-benzamide
(Table 2, Entry 1)
9,¹8
White solid; mp 235-237 ˚C. IR (KBr): νmax = 1625,
3065, 3418 cm-¹. ¹H
NMR (300 MHz, DMSO-d
6): δ = 7.20-7.90 (m,
16 H), 8.10-8.13 (d, 1 H, J = 8.4
Hz), 9.02 (d, 1 H, J = 8.4
Hz), 10.33 (s, 1 H, NH) ppm. ¹³C NMR
(75 MHz, DMSO-d
6): δ = 50.0,
119.1, 119.4, 123.4, 127.1, 127.2, 127.5, 127.8, 128.9, 129.1, 129.2,
129.3, 130.1, 132.1, 133.0, 135.0, 142.7, 147.0, 153.9, 166.4 ppm.
N
-[(2-Hydroxynaphthalen-1-yl)(4-nitrophenyl)methyl]-benzamide
(Table 2, Entry 2)
²9,8
Yellow solid; mp 247-249 ˚C. IR (KBr): νmax = 1641,
3234, 3410 cm-¹. ¹H
NMR (300 MHz, DMSO-d
6): δ = 7.22-7.56 (m,
9 H), 7.82-7.91 (m, 4 H), 8.06 (d, 1 H, J = 8.4
Hz), 8.14 (d, 2 H, J = 8.4
Hz), 9.04 (d, 1 H, J = 8.1
Hz), 10.35 (s, 1 H, NH) ppm. ¹³C NMR
(75 MHz, DMSO-d
6): δ = 49.1,
117.4, 118.6, 122.6, 122.8, 123.4, 127.0, 127.4, 127.5, 128.4, 128.7,
130.0, 131.6, 132.2, 134.0, 146.2, 150.2, 153.4, 166.3 ppm.
N
-[(2-Hydroxynaphthalen-1-yl)(
p
-tolyl)methyl]-benzamide
(Table 2, Entry 3)
8,9
White solid; mp 223-225 ˚C.
IR (KBr): νmax = 1627,
3043, 3413 cm-¹. ¹H
NMR (300 MHz, DMSO-d
6): δ = 1.97
(s, 3 H, CH3), 2.23 (s, 3 H, CH3), 7.05-7.38
(m, 8 H), 7.74-7.81 (m, 2 H), 7.85 (d, 1 H, J = 8.4 Hz),
8.38 (d, 1 H, J = 8.4
Hz), 9.94 (s, 1 H, NH) ppm. ¹³C NMR
(75 MHz, DMSO-d
6): δ = 20.5, 22.6,
47.6, 118.4, 119.0, 122.3, 126.0, 126.2, 128.5, 129.0, 132.3, 135.0,
139.5, 153.0, 169.0 ppm.
N
-[1-(2-Hydroxynaphthalen-1-yl)butyl]benzamide (Table
2, Entry 6)
³0
White solid; mp 240-242 ˚C. IR (KBr): νmax = 3415,
3222, 3204, 1633, 1575, 1528, 1342, 1074, 815, 747, 716 cm-¹. ¹H NMR
(300 MHz, DMSO-d
6): δ = 10.09
(s, 1 H), 8.60 (d, 1 H, J = 6.3
Hz), 8.23 (d, 1 H, J = 7.6
Hz), 7.81 (t, 3 H, J = 7.2 Hz),
7.71 (d, 1 H, J = 8.8
Hz), 7.53-7.44 (m, 4 H), 7.31 (t, 1 H, J = 7.3
Hz), 7.20 (d, 1 H, J = 8.8
Hz), 6.04 (q, 1 H, J = 7.1 Hz),
2.15-2.10 (m, 1 H), 1.90-1.80 (m, 1 H), 1.51-1.42
(m, 1 H), 1.30-1.20 (m, 1 H), 0.95 (t, 3 H, J = 7.3 Hz)
ppm. ¹³C NMR (75 MHz, DMSO-d
6): δ = 165.2,
152.8, 134.7, 132.1, 131.1, 128.5, 128.4, 128.3, 128.2, 126.9, 126.3,
122.3, 119.8, 118.6, 118.5, 46.6, 36.0, 19.6, 13.8 ppm.
N
-[Phenyl-(2-hydroxy-naphthalen-1-yl)-methyl]-acetamide
(Table 2, Entry 7)
¹¹,²8
White solid; mp 232-233 ˚C. IR (KBr): νmax = 3390,
3246, 3062, 1640, 1582, 1514, 1372, 1337, 1060, 808, 742, 696, 623
cm-¹. ¹H NMR (300
MHz, CDCl3): δ = 1.95
(s, 3 H), 7.10 (m, 1 H), 7.12 (m, 1 H), 7.15 (m, 1 H), 7.17 (m,
1 H), 7.20 (m, 2 H), 7.21 (m, 1 H), 7.25 (m, 1 H), 7.35 (t, 1 H, J = 7.5 Hz),
7.70 (d, 1 H, J = 9.1
Hz) ppm. ¹³C NMR (75 MHz, DMSO-d
6): δ = 23.2,
40.3, 119.2, 122.9, 123.8, 126.6, 126.8, 128.5, 128.8, 128.9, 129.1,
129.8, 132.8, 143.1, 153.7, 169.0 ppm.
4-Bromo-
N
-[(2-hydroxynaphthalen-1-yl)(phenyl)-methyl]benzamide
(Table 2, Entry 10)
Yellow solid; mp 239-242 ˚C.
IR (KBr): νmax = 3408,
3246, 3146, 1626 cm-¹. ¹H
NMR (400 MHz, DMSO-d
6): δ = 7.22 (m,
7 H), 7.41 (t, 2 H, J = 8.0
Hz), 7.66 (t, 2 H, J = 4.4
Hz), 7.78 (m, 4 H), 8.02 (d, 1 H, J = 8.0
Hz), 7.20 (m, 2 H), 9.08 (d, J = 4.0
Hz, 1 H), 10.26 (s, 1 H) ppm. ¹³C NMR
(100 MHz, DMSO-d
6): δ = 49.7,
115.5, 118.2, 122.6, 126.8, 128.3, 128.8, 128.9, 133.1, 142.8, 153.6,
167.8 ppm. Anal. Calcd for C24H18BrNO2:
C, 66.68; H, 4.20; Br, 18.48; N, 3.24; O, 7.40. Found: C, 66.75;
H, 4.11; N, 3.15.