A. Heydari et al. / Tetrahedron Letters 50 (2009) 77–80
79
NMR (500 MHz, CDCl3): d = 1.33–1.50 (m, 6H), 1.54–2.10 (4H, m),
3.64 (d, J = 10.4 Hz, 3H), 3.66 (d, J = 10.4 Hz, 3H), 4.84 (br s, 1 H),
7.00 (t, J = 7.1 Hz, 1H), 7.13 (d, J = 8.1 Hz, 2H), 7.16 (t, J = 8.1 Hz,
2H). 13C NMR (125 MHz, CDCl3): d = 19.7 (CH2), 25.6 (CH2), 25.1
(CH2), 52.2 (d, JP–C = 7.4 Hz, OCH3), 53.2 (d, JP–C = 7.4 Hz, OCH3),
65.2 (d, JP–C = 155.1 Hz, C), 118.2 (CH), 118.3 (CH), 129.1 (CH),
145.5 (C).
O
R3
R2
R1
R4
R1
R2
N
1
TFE, r.t. 5 h
2
2
P(OMe)3
O
+
P
H
N
4
OMe
MeO
R3
R4
5
2
Acknowledgment
Entry
1
Aldehyde/Ketone
CHO
Amine
NH2
Yield (%)a of 5
This research is supported by the National Research Council of
I.R. Iran as National Research Project Number 984.
97 25h
NH2
CHO
CHO
References and notes
93 25l
2
Cl
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NH2
NH2
85 28
93 25l
95 25h
95 25l
90 25l
3
4
NC
CHO
3. Niimi, L.; Serita, K.-I.; Hiraoka, S.; Yokozawa, T. Tetrahedron Lett. 2000, 41,
7075.
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NH2
NH2
CHO
5
6
CHO
CHO
O
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1513.
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1980, 861.
NH2
7
8
NH2
CHO
CHO
82 28
Cl
N
H
80 25h
9
14. Heydari, A.; Fatemi, P.; Alizadeh, A. A. Tetrahedron Lett. 1998, 39, 3049.
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Meier, A.; Buschmann, J.; Luger, P. Synthesis 1996, 123.
CHO
CHO
90 25l
92 28
10
11
N H
O
NH2
19. De, S. K. Synth. Commun. 2005, 35, 653.
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MeO
NH2
NH2
O
95 25l
12
13
23. Previously, some methods have failed to produce
a-aminonitriles from
O
85 25l
conjugated aldehydes Ranu, B. C.; Dey, S. S.; Hajra, A. Tetrahedron 2002, 58,
2529.
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Chem. Soc., Perkin Trans. 1 1998, 131.
a The spetral data (1H, 13C NMR) of known compounds were found
to be identical with those reported in the literature.
Scheme 2.
25. Microreactor: (a) Van Meenen, E.; Moonen, K.; Acke, D.; Stevens, C. V. ARKIVOC
2006, 31; Lewis acids including lanthanide triflate (b) Manabe, K.; Kobayashi, S.
Chem. Commun. 2000, 669; Samarium diiodide: (c) Xu, F.; Luo, Y.; Deng, M.;
Shen, Q. Eur. J. Org. Chem. 2003, 4728; Scandium tris(dodecylsulfate): (d)
Manabe, K.; Kobayashi, S. Chem. Commun. 2000, 669; Indium(III) chloride: (e)
Ranu, B. C.; Hajra, A.; Jana, J. Org. Lett. 1999, 1, 1141; TaCl5–SiO2: (f)
Chandrasekhar, S.; Jaya Prakash, S.; Jagadeshwar, V.; Narsihmula, Ch.
Tetrahedron Lett. 2001, 42, 5561; (Bromodimethyl)sulfonium bromide: (g)
Kudrimoti, S.; Rao Bommena, V. Tetrahedron Lett. 2005, 46, 1209; Lithium
perchlorate: (h) Heydari, A.; Zarei, M.; Alijanianzadeh, R.; Tavakol, H.
Tetrahedron Lett. 2001, 42, 3629; Alumina-supported reagents as catalysts: (i)
Kaboudin, B.; Nazari, R. Tetrahedron Lett. 2001, 42, 8211. Although this
phosphite (1 mmol) in TFE (1 mL) was stirred at ambient temper-
ature for the appropriate amount of time (5 h). After completion
of the reaction as indicated by TLC, the TFE was separated by dis-
tillation and the crude product was purified by recrystallization
from diethyl ether (solid products) or by chromatography using sil-
ica gel and mixtures of hexane/ethyl acetate of increasing polarity.
The physical data (mp, IR, NMR) of known compounds were found
to be identical with those reported in the literature.25h,25l,28 Spec-
troscopic data for a selected example: (Scheme 2, entry 12)25l 1H
: