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Cobalt(II) chloride accelerated one-pot three-component synthesis of α-aminophosphonates at room temperature
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Chinese Chemical Letters 22 (2011) 559–562 www.elsevier.com/locate/cclet
Cobalt(II) chloride accelerated one-pot three-component synthesis of a-aminophosphonates at room temperature Zahed Karimi-Jaberi *, Hassan Zare, Mohammad Amiri, Naghmeh Sadeghi Department of Chemistry, Islamic Azad University, Firoozabad Branch, P.O. Box 74715-117, Firoozabad, Fars, Iran Received 10 September 2010 Available online 2 March 2011
Abstract A simple, efficient, and general method has been developed for the one-pot, three-component synthesis of a-aminophosphonates from condensation reaction of trimethyl phosphite, aryl aldehydes and aryl amines in the presence of CoCl26H2O under solventfree conditions. Thus a-aminophosphonates were synthesized relatively quickly in good yields at room temperature. # 2010 Zahed Karimi-Jaberi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. Keywords: a-Aminophosphonates; Cobalt(II) chloride; Trimethyl phosphite; Room temperature; Solvent-free
The synthesis of a-aminophosphonates as analogous of natural a-aminoacids has attracted a significant interest by organic chemists in recent years. They have been attracting a good deal of attention ever since the first compounds with a phosphorus–carbon bond were detected among natural products. Their diverse applications include as enzyme inhibitors, antibiotics, pharmacological agents and many other applications are well documented [1–4]. Peptido mimetics made out of this class of compounds have shown promising pharmacological properties [5]. Thus, a variety of synthetic approaches are desirable to synthesize a-amino phosphonates [6]. One-pot three-component condensation of aldehydes, amines, and dimethylphosphite or trimethylphosphite is the most convenient method for the preparation of these compounds. In this context some methods and catalysts have been reported [7–16]. Although, these approaches are satisfactory for synthesis of a-aminophosphonates, the harsh reaction conditions, expensive reagents, use of toxic organic solvents and long reaction time limit the use of these methods. Due to extending our interest in the development of practical, safe, and environmentally friendly procedures for several important organic transformations [16–19], we now describe a simple, general and efficient protocol for the synthesis of a-aminophosphonates via three-component reactions of aldehydes, amines, and trimethyl phosphite using catalytic amounts of cobalt chloride under solvent-free conditions at room temperature. Cobalt(II) chloride is an efficient catalyst which has been successfully utilized in numerous reactions, for example, synthesis of 1,2,5-trisubstituted pyrroles [20], chemoselective thioacetalization of aldehydes [21], reduction of azides [22], synthesis of acid anhydrides [23], and hydroformylation of olefins [24]. It offers milder conditions relative to common mineral acids. Cobalt(II) chloride is a readily available and inexpensive reagent and can conveniently be
* Corresponding author. E-mail address: [email protected] (Z. Karimi-Jaberi). 1001-8417/$ – see front matter # 2010 Zahed Karimi-Jaberi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. doi:10.1016/j.cclet.2010.11.034
[()TD$FIG] 560
Z. Karimi-Jaberi et al. / Chinese Chemical Letters 22 (2011) 559–562 R' O R
H 1
+
R'NH2 + 2
MeO
P
OMe
OMe
CoCl2.6H2O R.T., neat
NH
O P OMe OMe
R 3
Scheme 1. Synthesis of a-aminophosphonates.
handled and removed from the reaction mixture. Thus, the remarkable catalytic activities together with its operational simplicity make it the most suitable catalyst for the synthesis of a-aminophosphonates. In order to optimize the reaction conditions, the reaction between benzaldehyde, aniline and trimethyl phosphite was used as a model reaction. The optimized reactant ratios were found to be 1.0 equiv. benzaldehyde, 1.0 equiv. aniline, and 1.0 equiv. trimethylphosphite in the presence of 1.0 equiv. solid CoCl26H2O. The expected aminophosphonate was produced in 96% yield after 15 min at room temperature without the use of any solvent (Scheme 1). After completion of the reaction, the catalyst (CoCl2) can easily be separated from the reaction mixture. To establish the generality and scope of the cobalt chloride promoted a-aminophosphonate synthesis, the reaction was examined with various structurally diverse aldehydes, amines and trimethylphosphite. The results are summarized in Table 1. Various functionalities present in the aryl aldehydes, such as halogen, methoxy, hydroxyl, cyano and nitro groups were tolerated (see Table 1). Furthermore, unsaturated aldehydes, such as cinnamaldehydes (Entry 9), gave the corresponding phosphonate without any polymerization or conjugate addition to the a,b-unsaturated carbonyl group under the above reaction conditions. The reaction can also proceed with several functionalities present in the aromatic amine. In all these cases, the corresponding a-aminophosphonates were obtained in good yields at room temperature without formation of any side products such as a-hydroxyphosphonate. Apart from the above amines, benzyl amine (entries 14–15) could provide the target products in reasonable yield. It is important to note that the synthesis of aaminophosphonates could not be achieved in the absence of catalyst (CoCl2). This method offers some advantages in terms of simplicity of performance, solvent free condition, and short reaction time. Several examples illustrating this novel and general method for the synthesis of a-aminophosphonates 3a-p are summarized in Table 1. All products are known compounds and structures of them were confirmed by comparison with their known physical and spectral (NMR and IR) data. In conclusion this paper describes a convenient and efficient process for the synthesis of a-aminophosphonates by one-pot reaction of trimethyl phosphite, aldehydes and amines in the presence of cobalt(II) chloride at room temperature under solvent-free conditions. 1. Experimental A mixture of aldehyde (1 mmol), amine (1 mmol), trimethyl phosphite (1 mmol) and CoCl26H2O (1 mmol) was stirred at room temperature for the appropriate time indicated in Table 1. After completion of the reaction, as indicated by TLC (ethyl acetate/n-hexane = 1/4), chloroform (10 mL) was added and the catalyst was recovered by filtration. Filtrates were evaporated to remove the solvent. The solid obtained was recrystallized from ethanol to afford pure products. Compound 3a: white solid, mp 87–89 8C; 1H NMR (CDCl3): d 3.51 (d, 3H, J = 10.5 Hz, OCH3), 3.81 (d, 3H, J = 10.6 Hz, OCH3), 4.82 (d, 1H, J = 24 Hz, CHP), 6.64 (d, 2H, J = 8.0 Hz, ArH), 6.74 (t, 1H, J = 7.2 Hz, ArH), 7.10 (t, 2H, J = 7.7 Hz, ArH), 7.30 (t, 1H, J = 7.5 Hz, ArH), 7.39 (t, 2H, J = 7.4 Hz, ArH), 7.50 (d, 2H, J = 7.3 Hz, ArH); 13 C NMR (CDCl3): d 54.1 (d, J = 7.0 Hz, OCH3), 54.2 (d, J = 6.8 Hz, OCH3), 56.2 (d, J = 150 Hz, CH), 114.3 (CH), 119.0 (CH), 128.2 (d, J = 5.8 Hz, CH), 128.4 (d, J = 3.1 Hz, CH), 129.1 (CH), 131.2 (CH), 136.0 (C), 146.6 (d, J = 14.5 Hz, C). Compound 3h: white solid, mp 109–111 8C; 1H NMR (CDCl3) d: 3.52 (d, 3H, J = 10.6 Hz, OCH3), 3.86 (d, 3H, J = 10.6 Hz, OCH3), 4.65 (br, 1H, NH), 5.35 (d, 1H, J = 24.7, CHP), 6.57 (d, 2H, J = 8.7 Hz), 6.73 (t, 1H, J = 8.6), 7.13 (t, 2H, J = 8.6), 7.21–7.26 (dd, 1H, J = 1.8, 8.4 Hz), 7.43 (s, 1H), 7.51–7.55 (dd, 1H, J = 2.5, 8.4 Hz); 13C NMR (CDCl3): d 51.2 (d, J = 153.1 Hz, CHP), 53.7 (d, J = 6.9 Hz, OCH3), 54.0 (d, J = 6.9 Hz, OCH3), 113.6, 118.7, 127.5 (d, J = 3.0 Hz), 128.9 (d, J = 4.2 Hz), 129.2, 129.30, 129.6 (d, J = 2.3 Hz), 133.7, 134.0 (d, J = 7.27 Hz), 145.5 (d, J = 14.6 Hz).
Z. Karimi-Jaberi et al. / Chinese Chemical Letters 22 (2011) 559–562
561
Table 1 Synthesis of a-amino phosphonates in the presence of CoCl26H2O. Entry
Aldehyde
1
[TD$INLE]
Amine
CHO
[TD$INLE]
O
NH2
[TD$INLE] MeO
P(OMe)2 N H
2a
CHO
[TD$INLE]
O
NH2
[TD$INLE]
1a 2
Product
1b
P(OMe)2
[TD$INLE]
2a
Time (min)
Yield (%)
3a
15
96
3b
15
95
3c
10
95
3d
10
92
3e
15
97
3f
30
93
3g
15
89
3h
25
91
3i
60
95
3j
10
86
3k
10
80
3l
60
93
3m
60
95
N H
MeO
CHO
[TD$INLE]
3
Cl
O
NH2
[TD$INLE]
[TD$INLE]
2a
1c
P(OMe)2 N H
Cl
CHO
[TD$INLE]
4
H 3C
O
NH2
[TD$INLE]
P(OMe)2
[TD$INLE]
2a
1d
N H H 3C
CHO
[TD$INLE] [TD$INLE]
5
O2N
O
NH2
1e
P(OMe) 2
[TD$INLE]
2a
N H O 2N
CHO
[TD$INLE] [TD$INLE]
6
NC
O
NH2
[TD$INLE]
2a
1f
P(OMe) 2 N H
NC CHO
[TD$INLE]
7
[TD$INLE]
HO
O
NH2
P(OMe) 2
[TD$INLE]
2a
1g
N H HO
CHO
[TD$INLE]
8
Cl
Cl
O
NH2
[TD$INLE]
1h
N H Cl
CHO
[TD$INLE]Ph
9
[TD$INLE]
[TD$INLE]
2a CHO
[TD$INLE]
10
Ph
Cl
1b
P(OMe) 2 N H O P(OMe)2
NH2
[TD$INLE]
MeO
Cl
O
NH2
1i
P(OMe)2
[TD$INLE]
2a
[TD$INLE]
N H
2b
Cl
MeO CHO
[TD$INLE]
11
MeO
O
NH2
[TD$INLE]
H3C
1b
P(OMe)2
[TD$INLE]
CH3
2c
N H MeO
12
[TD$INLE]
CHO
[TD$INLE]
1a
13
[TD$INLE]
O
NH2 Cl
[TD$INLE]
NH2
CHO
1a
[TD$INLE]
H3C
O
[TD$INLE]
2c
P(OMe)2 N H
2b
Cl
P(OMe)2 N H
CH 3
562
Z. Karimi-Jaberi et al. / Chinese Chemical Letters 22 (2011) 559–562
Table 1 (Continued ) Entry
Aldehyde
14
[TD$INLE]
Amine
CHO
Product O
NH2
[TD$INLE] [TD$INLE]
1a
CHO
[TD$INLE]
Cl
O
NH2
[TD$INLE]
P(OMe)2
[TD$INLE]
1c
Yield (%)
3n
15
96
3o
30
91
3p
10
87
N H
2d
15
P(OMe)2
Time (min)
N H
2d Cl
CHO
16
[TD$INLE]
HO
O
NH2
1g
[TD$INLE]
Cl
2b
[TD$INLE]
P(OMe) 2 N H
Cl
HO
References [1] [2] [3] [4] [5] [6] [7] [8] [9] [10] [11] [12] [13] [14] [15] [16] [17] [18] [19] [20] [21] [22] [23] [24]
F.R. Atherton, C.H. Hassal, R.W. Lambert, J. Med. Chem. 29 (1986) 29. Kafarski, B. Lejczak, Phosphorous, Sulphur, Silicon Relat. Elem. 63 (1991) 193. M.C. Allen, W. Fuhrer, B. Tuck, J.M. Wood, et al. J. Med. Chem. 32 (1989) 1652. V.P. Kukhar, H.R. Hudson, Aminophosphonic and Aminophosphinic Acids, Wiley, Chichester, UK, 2000. E.K. Baylis, C.D. Campbell, J.G. Dingwall, J. Chem. Soc. Perkin Trans. 1 (1984) 2845. R. Engel, J.I. Cohen, Synthesis of Carbon–Phosphorus Bonds, CRC Press, 2003. S.M. Vahdat, R. Baharfar, M. Tajbakhsh, et al. Tetrahedron Lett. 49 (2008) 6501. B. Kaboudin, M. Sorbiun, Tetrahedron Lett. 48 (2007) 9015. J. Wu, W. Sun, H. Xia, et al. Org. Biomol. Chem. 4 (2006) 1663. A.K. Bhattacharya, T. Kaur, Synlett 5 (2007) 745. X. Mu, M. Lei, J. Zoua, et al. Tetrahedron Lett. 47 (2006) 1125. J. Akbari, A. Heydari, Tetrahedron Lett. 50 (2009) 4236. M. Hosseini-Sarvari, Tetrahedron 64 (2008) 5459. M. Maghsoodlou, S.M.H. Khorassani, N. Hazeri, et al. Heteroatom Chem. 20 (2009) 316. N. Azizi, M.R. Saidi, Eur. J. Org. Chem. (2003) 4630. Z. Karimi-Jaberi, M. Amiri, Heteroatom Chem. 21 (2010) 96. Z. Karimi-Jaberi, M. Keshavarzi, Chin. Chem. Lett. 21 (2010) 547. Z. Karimi-Jaberi, M. Barekat, Chin. Chem. Lett. 21 (2010) 1183. Z. Karimi-Jaberi, M.M. Hashemi, Monatsh. Chem. 139 (2008) 605. S.K. De, Heteroatom Chem. 19 (2008) 592. S.K. De, Tetrahedron Lett. 45 (2004) 1035. F. Fringuelli, F. Pizzo, L. Vaccaro, Synthesis (2000) 646. R.R. Srivastava, G.W. Kabalka, Tetrahedron Lett. 33 (1992) 593. A.A. Dabbawala, D.U. Parmar, H.C. Bajaj, et al. J. Mol. Catal. A: Chem. 282 (2008) 99.
Chinese Chemical Letters 22 (2011) 559–562 www.elsevier.com/locate/cclet
Cobalt(II) chloride accelerated one-pot three-component synthesis of a-aminophosphonates at room temperature Zahed Karimi-Jaberi *, Hassan Zare, Mohammad Amiri, Naghmeh Sadeghi Department of Chemistry, Islamic Azad University, Firoozabad Branch, P.O. Box 74715-117, Firoozabad, Fars, Iran Received 10 September 2010 Available online 2 March 2011
Abstract A simple, efficient, and general method has been developed for the one-pot, three-component synthesis of a-aminophosphonates from condensation reaction of trimethyl phosphite, aryl aldehydes and aryl amines in the presence of CoCl26H2O under solventfree conditions. Thus a-aminophosphonates were synthesized relatively quickly in good yields at room temperature. # 2010 Zahed Karimi-Jaberi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. Keywords: a-Aminophosphonates; Cobalt(II) chloride; Trimethyl phosphite; Room temperature; Solvent-free
The synthesis of a-aminophosphonates as analogous of natural a-aminoacids has attracted a significant interest by organic chemists in recent years. They have been attracting a good deal of attention ever since the first compounds with a phosphorus–carbon bond were detected among natural products. Their diverse applications include as enzyme inhibitors, antibiotics, pharmacological agents and many other applications are well documented [1–4]. Peptido mimetics made out of this class of compounds have shown promising pharmacological properties [5]. Thus, a variety of synthetic approaches are desirable to synthesize a-amino phosphonates [6]. One-pot three-component condensation of aldehydes, amines, and dimethylphosphite or trimethylphosphite is the most convenient method for the preparation of these compounds. In this context some methods and catalysts have been reported [7–16]. Although, these approaches are satisfactory for synthesis of a-aminophosphonates, the harsh reaction conditions, expensive reagents, use of toxic organic solvents and long reaction time limit the use of these methods. Due to extending our interest in the development of practical, safe, and environmentally friendly procedures for several important organic transformations [16–19], we now describe a simple, general and efficient protocol for the synthesis of a-aminophosphonates via three-component reactions of aldehydes, amines, and trimethyl phosphite using catalytic amounts of cobalt chloride under solvent-free conditions at room temperature. Cobalt(II) chloride is an efficient catalyst which has been successfully utilized in numerous reactions, for example, synthesis of 1,2,5-trisubstituted pyrroles [20], chemoselective thioacetalization of aldehydes [21], reduction of azides [22], synthesis of acid anhydrides [23], and hydroformylation of olefins [24]. It offers milder conditions relative to common mineral acids. Cobalt(II) chloride is a readily available and inexpensive reagent and can conveniently be
* Corresponding author. E-mail address: [email protected] (Z. Karimi-Jaberi). 1001-8417/$ – see front matter # 2010 Zahed Karimi-Jaberi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. doi:10.1016/j.cclet.2010.11.034
[()TD$FIG] 560
Z. Karimi-Jaberi et al. / Chinese Chemical Letters 22 (2011) 559–562 R' O R
H 1
+
R'NH2 + 2
MeO
P
OMe
OMe
CoCl2.6H2O R.T., neat
NH
O P OMe OMe
R 3
Scheme 1. Synthesis of a-aminophosphonates.
handled and removed from the reaction mixture. Thus, the remarkable catalytic activities together with its operational simplicity make it the most suitable catalyst for the synthesis of a-aminophosphonates. In order to optimize the reaction conditions, the reaction between benzaldehyde, aniline and trimethyl phosphite was used as a model reaction. The optimized reactant ratios were found to be 1.0 equiv. benzaldehyde, 1.0 equiv. aniline, and 1.0 equiv. trimethylphosphite in the presence of 1.0 equiv. solid CoCl26H2O. The expected aminophosphonate was produced in 96% yield after 15 min at room temperature without the use of any solvent (Scheme 1). After completion of the reaction, the catalyst (CoCl2) can easily be separated from the reaction mixture. To establish the generality and scope of the cobalt chloride promoted a-aminophosphonate synthesis, the reaction was examined with various structurally diverse aldehydes, amines and trimethylphosphite. The results are summarized in Table 1. Various functionalities present in the aryl aldehydes, such as halogen, methoxy, hydroxyl, cyano and nitro groups were tolerated (see Table 1). Furthermore, unsaturated aldehydes, such as cinnamaldehydes (Entry 9), gave the corresponding phosphonate without any polymerization or conjugate addition to the a,b-unsaturated carbonyl group under the above reaction conditions. The reaction can also proceed with several functionalities present in the aromatic amine. In all these cases, the corresponding a-aminophosphonates were obtained in good yields at room temperature without formation of any side products such as a-hydroxyphosphonate. Apart from the above amines, benzyl amine (entries 14–15) could provide the target products in reasonable yield. It is important to note that the synthesis of aaminophosphonates could not be achieved in the absence of catalyst (CoCl2). This method offers some advantages in terms of simplicity of performance, solvent free condition, and short reaction time. Several examples illustrating this novel and general method for the synthesis of a-aminophosphonates 3a-p are summarized in Table 1. All products are known compounds and structures of them were confirmed by comparison with their known physical and spectral (NMR and IR) data. In conclusion this paper describes a convenient and efficient process for the synthesis of a-aminophosphonates by one-pot reaction of trimethyl phosphite, aldehydes and amines in the presence of cobalt(II) chloride at room temperature under solvent-free conditions. 1. Experimental A mixture of aldehyde (1 mmol), amine (1 mmol), trimethyl phosphite (1 mmol) and CoCl26H2O (1 mmol) was stirred at room temperature for the appropriate time indicated in Table 1. After completion of the reaction, as indicated by TLC (ethyl acetate/n-hexane = 1/4), chloroform (10 mL) was added and the catalyst was recovered by filtration. Filtrates were evaporated to remove the solvent. The solid obtained was recrystallized from ethanol to afford pure products. Compound 3a: white solid, mp 87–89 8C; 1H NMR (CDCl3): d 3.51 (d, 3H, J = 10.5 Hz, OCH3), 3.81 (d, 3H, J = 10.6 Hz, OCH3), 4.82 (d, 1H, J = 24 Hz, CHP), 6.64 (d, 2H, J = 8.0 Hz, ArH), 6.74 (t, 1H, J = 7.2 Hz, ArH), 7.10 (t, 2H, J = 7.7 Hz, ArH), 7.30 (t, 1H, J = 7.5 Hz, ArH), 7.39 (t, 2H, J = 7.4 Hz, ArH), 7.50 (d, 2H, J = 7.3 Hz, ArH); 13 C NMR (CDCl3): d 54.1 (d, J = 7.0 Hz, OCH3), 54.2 (d, J = 6.8 Hz, OCH3), 56.2 (d, J = 150 Hz, CH), 114.3 (CH), 119.0 (CH), 128.2 (d, J = 5.8 Hz, CH), 128.4 (d, J = 3.1 Hz, CH), 129.1 (CH), 131.2 (CH), 136.0 (C), 146.6 (d, J = 14.5 Hz, C). Compound 3h: white solid, mp 109–111 8C; 1H NMR (CDCl3) d: 3.52 (d, 3H, J = 10.6 Hz, OCH3), 3.86 (d, 3H, J = 10.6 Hz, OCH3), 4.65 (br, 1H, NH), 5.35 (d, 1H, J = 24.7, CHP), 6.57 (d, 2H, J = 8.7 Hz), 6.73 (t, 1H, J = 8.6), 7.13 (t, 2H, J = 8.6), 7.21–7.26 (dd, 1H, J = 1.8, 8.4 Hz), 7.43 (s, 1H), 7.51–7.55 (dd, 1H, J = 2.5, 8.4 Hz); 13C NMR (CDCl3): d 51.2 (d, J = 153.1 Hz, CHP), 53.7 (d, J = 6.9 Hz, OCH3), 54.0 (d, J = 6.9 Hz, OCH3), 113.6, 118.7, 127.5 (d, J = 3.0 Hz), 128.9 (d, J = 4.2 Hz), 129.2, 129.30, 129.6 (d, J = 2.3 Hz), 133.7, 134.0 (d, J = 7.27 Hz), 145.5 (d, J = 14.6 Hz).
Z. Karimi-Jaberi et al. / Chinese Chemical Letters 22 (2011) 559–562
561
Table 1 Synthesis of a-amino phosphonates in the presence of CoCl26H2O. Entry
Aldehyde
1
[TD$INLE]
Amine
CHO
[TD$INLE]
O
NH2
[TD$INLE] MeO
P(OMe)2 N H
2a
CHO
[TD$INLE]
O
NH2
[TD$INLE]
1a 2
Product
1b
P(OMe)2
[TD$INLE]
2a
Time (min)
Yield (%)
3a
15
96
3b
15
95
3c
10
95
3d
10
92
3e
15
97
3f
30
93
3g
15
89
3h
25
91
3i
60
95
3j
10
86
3k
10
80
3l
60
93
3m
60
95
N H
MeO
CHO
[TD$INLE]
3
Cl
O
NH2
[TD$INLE]
[TD$INLE]
2a
1c
P(OMe)2 N H
Cl
CHO
[TD$INLE]
4
H 3C
O
NH2
[TD$INLE]
P(OMe)2
[TD$INLE]
2a
1d
N H H 3C
CHO
[TD$INLE] [TD$INLE]
5
O2N
O
NH2
1e
P(OMe) 2
[TD$INLE]
2a
N H O 2N
CHO
[TD$INLE] [TD$INLE]
6
NC
O
NH2
[TD$INLE]
2a
1f
P(OMe) 2 N H
NC CHO
[TD$INLE]
7
[TD$INLE]
HO
O
NH2
P(OMe) 2
[TD$INLE]
2a
1g
N H HO
CHO
[TD$INLE]
8
Cl
Cl
O
NH2
[TD$INLE]
1h
N H Cl
CHO
[TD$INLE]Ph
9
[TD$INLE]
[TD$INLE]
2a CHO
[TD$INLE]
10
Ph
Cl
1b
P(OMe) 2 N H O P(OMe)2
NH2
[TD$INLE]
MeO
Cl
O
NH2
1i
P(OMe)2
[TD$INLE]
2a
[TD$INLE]
N H
2b
Cl
MeO CHO
[TD$INLE]
11
MeO
O
NH2
[TD$INLE]
H3C
1b
P(OMe)2
[TD$INLE]
CH3
2c
N H MeO
12
[TD$INLE]
CHO
[TD$INLE]
1a
13
[TD$INLE]
O
NH2 Cl
[TD$INLE]
NH2
CHO
1a
[TD$INLE]
H3C
O
[TD$INLE]
2c
P(OMe)2 N H
2b
Cl
P(OMe)2 N H
CH 3
562
Z. Karimi-Jaberi et al. / Chinese Chemical Letters 22 (2011) 559–562
Table 1 (Continued ) Entry
Aldehyde
14
[TD$INLE]
Amine
CHO
Product O
NH2
[TD$INLE] [TD$INLE]
1a
CHO
[TD$INLE]
Cl
O
NH2
[TD$INLE]
P(OMe)2
[TD$INLE]
1c
Yield (%)
3n
15
96
3o
30
91
3p
10
87
N H
2d
15
P(OMe)2
Time (min)
N H
2d Cl
CHO
16
[TD$INLE]
HO
O
NH2
1g
[TD$INLE]
Cl
2b
[TD$INLE]
P(OMe) 2 N H
Cl
HO
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