Mild and efficient method for regioselective ring opening of aziridines with amines by bismuth trichloride

Article abstract of DOI:10.1081/SCC-120015808

Aziridines undergo the facile ring opening with anilines to afford the 1,2-diamines in excellent yields by bismuth trichloride in acetonitrile at ambient temperature.

Full text of DOI:10.1081/SCC-120015808

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Mild and Efficient Method for Regioselective Ring
Opening of Aziridines with Amines by Bismuth
Trichloride
Navath Raghavendra Swamy a & Y. Venkateswarlu a
a Organic Chemistry Division-I , Indian Institute of Chemical Technology , Hyderabad, India
Published online: 16 Aug 2006.
To cite this article: Navath Raghavendra Swamy & Y. Venkateswarlu (2003) Mild and Efficient Method for Regioselective Ring
Opening of Aziridines with Amines by Bismuth Trichloride, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 33:4, 547-554, DOI: 10.1081/SCC-120015808
To link to this article: http://dx.doi.org/10.1081/SCC-120015808
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SYNTHETIC COMMUNICATIONSÕ
Vol. 33, No. 4, pp. 547–554, 2003
Mild and Efficient Method for Regioselective
Ring Opening of Aziridines with Amines by
Bismuth Trichloride#
Navath Raghavendra Swamy and Y. Venkateswarlu*
OrganicChemistry Division-I, Indian Institute of
Chemical Technology, Hyderabad, India
ABSTRACT
Aziridines undergo the facile ring opening with anilines to afford the
1,2-diamines in excellent yields by bismuth trichloride in acetonitrile
at ambient temperature.
1,2-Diamines are biologically and medicinally important class of
compounds in the field of drugs and pharmaceuticals.[1] One of the
most straightforward synthetic procedures for the formation of vicinal
diamines is the ring opening of aziridines with amines. However, this
#IICT communication no: 4863.
*Correspondence: Y. Venkateswarlu, Organic Chemistry Division-I, Indian
Institute of Chemical Technology, Hyderabad 500 007, India; Fax: þ91-40-
7160512; E-mail: luchem@iict.ap.nic..
547
DOI: 10.1081/SCC-120015808
Copyright & 2003 by Marcel Dekker, Inc.
0039-7911 (Print); 1532-2432 (Online)
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548
Swamy and Venkateswarlu
classical method has been disregarded primarily due to limitations of the
reaction conditions. There is significant current interest in the synthesis
of aziridines intermediates in the preparation of nitrogen containing
molecules like amino acids,[2] heterocycles,[3,4] alkaloids,[5] and their
N-activated analogues.[6] The Lewis acid induced ring opening of
N-substituted aziridines with several nucleophiles such as TMSN3,
TMSCN, has been very well studied[7–11] and ring opening reaction of
activated aziridines with amines has been reported in the presence of tin
triflate,[10] copper triflate,[10] and yetterbium triflate[12] as catalysts. These
procedures required longer reaction time, higher concentration of the
catalyst (20 mol%), and these metal triflates are highly expensive. There
is a merit in developing a truly catalytic process for ring opening of
aziridines with amines using inexpensive and non-polluting reagents.
We discovered that aziridines could be efficiently cleaved with amines
as well as less reactive aromatic amines using 10 mol% of BiCl3.
Herein, we wish to report that bismuth trichloride catalyzed ring opening
of aziridines with amines. The reaction proceeds efficiently at ambient
temperature and the products are obtained in excellent yields.
Furthermore, other functional groups such as OH, OMe, NO2, Ts, are
compatible under the reaction conditions. The reaction conditions are
very mild therefore no by-products are formed (Sch. 1).
A variety of aziridines were synthesized from the corresponding
amino alcohol in one step using MsCl (1.1 equiv) and Et3N (2.5 equiv)
in pyridine (as solvent) at room temperature. To show the scope of the
reaction we extended it to a variety of cyclic and acyclic aziridines with
substituted aromatic amines in the ring opening reaction. In most cases a
high yield of the opened product is isolated. The worthy feature of the
Scheme 1.

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Regioselective Ring Opening of Aziridines
549
reaction is that highly deactivated amine such as 4-nitroaniline also
opened aziridines in high yield. We first examined the reaction of
N-tosyl aziridine with aniline in the presence of bismuth trichloride in
acetonitrile at ambient temperature to afford the corresponding 1,2-
diamine in 96% yield (Entry a). This success has encouraged us to
extend the generality of the reaction to other aziridines with various
amines (Table 1). For example 2-OH aniline (Entry f ), 2-OMe aniline
(Entry g), 4-NO2 aniline (Entry i), reacted well to give corresponding
1,2-diamines in excellent yields. All the products are fully characterized
1
by IR, H NMR, 13C NMR, and mass spectral data. The trans stereo-
chemistry of 1,2-diamines (Entry) was determined from the coupling
constants of ring methine protons at ꢀ 2.24 (ddd, J ¼ 4.0, 10.0, and
10.0 Hz, 1H) and 2.67 (ddd, J ¼ 4.0, 10.0, and 10.0 Hz, 1H) of NCH
1
respectively in H NMR spectrum.
Probable mechanism for the present ring opening reaction is
conceivable, where BiCl3 acts as a Lewis acid, which coordinates the
nitrogen atom of the aziridines and facilitates the ring opening reaction
with amines.
In conclusion the present procedure for the preparation of 1,2-
diamines has advantages of mild reaction conditions, reduced reaction
time, inexpensive catalyst, high yields of products, and simple experimen-
tal work-up procedure which makes it an useful and important addition
to the present existing methodologies.
EXPERIMENTAL SECTION
General Procedure for the Generation of 1,2-Diamines
from Aziridines
To a solution of BiCl3 (10 mol%) in acetonitrile (15 mL) were added
aziridine (1 mmol) and amine (1.3 mmol) and the mixture was stirred at
room temperature under N2 atmosphere. After 2 h the solvent was
removed water was added and extracted into dichloromethane. The
organiclayer was washed with brine, dried over anhydrous Na 2SO4
and concentrated under reduced pressure to give crude diamine. The
crude product was purified over silica gel column chromatography to
give trans-1,2 diamino compound in good yield.
trans-N-(4-Methylbenzene sulfonyl)-2 anilinocyclohexamine (a):
Colorless oil, IR (neat): 3400, 3290, 1600, 1510, 1450, 1330, 1300, 1160,
900 cmÀ1; 1H NMR (CDCl3, 200 MHz): ꢀ 7.75 (2H, m), 7.31 (2H, m), 7.14
(2H, m), 6.71 (1H, m), 6.47 (2H, m), 3.10 (1H, br s), 2.97 (1H, ddd,

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550
Swamy and Venkateswarlu
Table 1. BiCl3 catalyzed aziridines opening with amines.
Yield
(%)b
Time
(h)
Entry
a
Diaminesa
96
94
93
1.5
b
c
2
1.5
d
94
95
2
2
e R1 ¼ HAr ¼ -C6H5
f R1 ¼ HAr ¼ -C6H4-o-OH
g R1 ¼ HAr ¼ -C6H4-o-Me
h R1 ¼ HAr ¼ -C6H4-p-O-Me
i R1 ¼ HAr ¼ -C6H4-p-NO2
93
94
93
92
2
2
2
2
j
95
94
93
1.5
k
l
2
2
1
aAll products were characterized by H NMR and mass spectrum and compared
the reported data.
bIsolated and unoptimized yields.
J ¼ 3.8, 10.0, 10.0 Hz, NCH), 2.91 (1H, m), 2.46 (3H, s), 2.03–2.20
(2H, m), 1.65 (2H, m), 1.55 (1H,m), 1.17–1.38 (2H, m), 0.94–1.11 (1H, m);
Anal. calcd. for C19H24N2O2S: C, 66.25; H, 7.02; N, 8.13. Found:
C, 66.25; H, 6.85; N, 8.06.
trans-N-Phenyl-N1( p-methoxyphenyl)-1,2-cyclohexanediamine
Colorless gel, IR (neat): 3365 cmÀ1 1H NMR (CDCl3, 200 MHz): ꢀ
(b):
;

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Regioselective Ring Opening of Aziridines
551
7.19 (m, 2H), 6.79 (m, 2H), 6.71 (m, 1H), 6.63 (m, 4H), 3.76 (s, 3H), 3.70
(br s, 2H, NH), 3.20 (ddd, J ¼ 9.6, 9.6, 3.3 Hz, 1H), 3.11 (ddd, J ¼ 9.6, 9.6,
3.3 Hz, 1H), 2.34 (m, 2H), 1.78 (m, 2H), 1.42 (m, 2H), 1.22 (m, 2H);
13C NMR (CDCl3, 50 MHz): ꢀ 152.4, 147.8, 141.8, 129.3, 117.6, 115.3,
115.0, 113.6, 58.4, 57.4, 55.8, 32.6, 24.6; EIMS: m/z 296 (Mþ); Anal.
calcd. for C19H24N2O; C, 77.03; H, 8.12; N, 9.46. Found: C, 76.78; H,
8.12; N, 9.40.
trans-N-Phenyl-N1(m-bromophenyl)-1,2-cyclohexanediamine
Semisolid, IR (KBr): 3390 cmÀ1 1H NMR (CDCl3, 200 MHz): ꢀ 7.21
(c):
;
(m, 2H), 7.02 (m, 1H), 6.84 (m, 1H), 6.74 (m, 2H), 6.65 (d, J ¼ 8.5 Hz, 2H),
6.52 (m, 1H), 3.82 (br s, 2H, NH), 3.19 (m, 2H), 2.38 (m, 2H), 1.81 (m, 2H),
1.45 (m, 2H), 1.22 (m, 2H).
trans-N-Phenyl-N1(o-methyl phenyl)-1,2-cyclohexanediamine (d):
Solid, m.p. 70–71ꢀC; IR (KBr): 3390 cmÀ1; 1H NMR (CDCl3, 200 MHz):
ꢀ 7.23 (m, 3H), 7.1 (d, J ¼ 7.5 Hz, 1H), 6.71 (m, 5H), 3.93 (br s, 2H, NH),
3.37 (ddd, J ¼ 9.9, 9.9, 3.9 Hz, 1H), 3.28 (ddd, J ¼ 9.6, 9.6, 3.6 Hz, 1H), 2.41
(m, 2H), 2.05 (s, 3H), 1.82 (m, 2H), 1.50 (m, 2H), 1.30 (m, 2H); 13C NMR
(CDCl3, 50 MHz), ꢀ 147.5, 145.6, 130.3, 129.3, 127.0, 122.9, 117.7, 117.1,
113.7, 110.2, 57.7, 57.3, 32.7, 32.6, 24.7, 24.6, 17.5; EIMS: m/z 280 (Mþ);
Anal. calcd. for C19H24N2: C, 81.43; H, 8.57; N, 10.0. Found: C, 81.46;
H, 8.70; N, 9.88.
trans-N,N1-Diphenyl-1,2-cyclohexane diamine (e): Colorless gel,
1H NMR (CDCl3, 200 MHz):
ꢀ
7.21 (dd, J ¼ 7.0 Hz, 4H), 6.75
(t, J ¼ 7 Hz, 2H), 6.62 (d, J ¼ 7.4 Hz, 1H), 3.92 (br s, 2H, NH), 3.24
(m, 2H), 2.39 (m, 2H), 1.8 (m , 2H), 1.42 (m, 2H), 1.23 (m, 2H);
13C NMR (CDCl3, 50 MHz): ꢀ 147.7, 129.3, 117.54, 113.47, 57.2, 32.5,
24.6; EIMS: m/z 266 (Mþ); Anal. calcd. for C18H22N2: C, 81.20; H, 8.27;
N, 10.53. Found: C, 81.02; H, 8.38; N, 10.60.
trans-N-Phenyl-N1 (2-hydroxyphenyl)-1,2-cyclohexanediamine
(f ):
1
Semisolid, H NMR (CDCl3, 200 MHz): ꢀ 7.20 (m, 3H), 6.80 (m, 6H),
4.40 (br s, 2H, NH), 3.20 (dt, J ¼ 9.9, 3.9 Hz, 1H), 2.93 (m, 1H), 2.21
(m, 2H), 1.68 (m, 2H), 1.25 (m, 4H); 13C NMR (CDCl3, 50 MHz): ꢀ 147.5,
147.0, 135.4, 129.6, 121.7, 120.5, 118.8, 114.7, 60.6, 58.5, 32.7, 32.5, 25.0,
24.9; EIMS: m/z 282 (Mþ); Anal. calcd. for C18H22N2O: C, 76.60; H, 7.80
N, 9.93. Found C, 76.62; H, 7.90; N, 9.84.
trans-N-Phenyl-N1-(o-methylphenyl)-1,2-cyclohexanediamine
(g):
Solid, m.p. 70–71ꢀC; IR (KBr) 3390 cmÀ1; H NMR (CDCl3, 200 MHz):
ꢀ 7.23 (m, 3H), 7.1 (d, J ¼ 7.5 Hz, 1H), 6.71 (m, 5H), 3.93 (br s, 2H, NH),
3.37 (ddd, J ¼ 9.9, 9.9, 3.9 Hz, 1H), 3.28 (ddd, J ¼ 9.6, 9.6, 3.6 Hz, 1H) 2.41
(m, 2H), 2.05 (s, 3H), 1.82 (m, 2H), 1.50 (m, 12H), 1.30 (m, 2H); 13C NMR
(CDCl3, 50 MHz): ꢀ 147.5, 145.6, 130.3, 129.3, 127.0, 122.9, 117.7, 117.1,
113.7, 110.2, 57.7, 57.3, 32.7, 32.6, 24.7, 24.6, 17.5; EIMS: m/z 280 (Mþ);
1

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Anal. calcd. for C19H24N2: C, 81.43; H, 8.57; N, 10.0. Found: C, 81.46; H,
8.70; N, 9.88.
trans-N-Phenyl-N1-( p-methoxyphenyl)-1,2-cyclohexanediamine (h):
1
Colorless gel; IR (neat) 3365 cmÀ1; H NMR (CDCl3, 200 MHz): ꢀ 7.19
(m, 2H), 6.79 (m, 2H), 6.71 (m, 1H), 6.63 (m, 4H), 3.76 (s, 3H), 3.70 (br s,
2H, NH), 3.20 (ddd, J ¼ 9.6, 9.6, 3.3 Hz, 1H), 3.11 (ddd, J ¼ 9.6, 3.3 Hz,
1H), 2.34 (m, 2H), 1.78 (m, 2H), 1.42 (m, 2H), 1.22 (m, 2H);13C NMR
(CDCl3, 50 MHz): ꢀ 152.4, 147.8, 141.8, 129.3, 117.6, 115.3, 115.0, 113.6,
58.4, 57.4, 55.8, 32.6, 24.6; EIMS: m/z 296 (Mþ) Anal. calcd. for
C19H24N2O; C, 77.03; H, 8.12; N, 9.46. Found: C, 76.78; H, 8.12; N,
9.40.
trans-N-Phenyl-N1-( p-nitrophenyl)-1,2-cyclohexanediamine
Yellow solid, m.p. 145ꢀC; IR (KBr) 3350 cmÀ1 1H NMR (CDCl3,
(i):
;
200 MHz): ꢀ 8.02 (m, 2H), 7.15 (m, 2H), 6.7 (m, 1H), 6.58 (m, 2H),
6.48 (m, 2H), 4.63 (br s, 1H, NH), 3.56 (br s, NH, 1H), 3.28 (m, 2H),
2.30 (m, 2H), 1.80 (m, 2H), 1.22–1.6 (b m, 4H); 13C NMR (CDCl3,
50 MHz): ꢀ 152.9, 147.1, 138, 129.5, 126.4, 118, 113.4, 111.5, 57.4, 56.9,
32.6, 32.2, 24.6, 24.4; EIMS: m/z 311 (Mþ); Anal. calcd. for C18H21N3O2:
C, 69.45; H, 6.75; N, 13.50. Found: C, 69.38; H, 6.82; N, 13.42.
trans-N,N1-Diphenyl-1,2-cyclopentanediamine ( j): Viscous liquid, IR
1
(neat): 3365 cmÀ1; H NMR (CDCl3, 200 MHz), ꢀ 7.18 (m, 4H), 6.70
(m, 2H), 6.64 (m, 4H), 3.78 (br s, 2H, NH), 3.6 (m, 2H), 2.21 (m, 2H),
8 (m, 2H), 1.5 (m, 2H); 13C NMR (CDCl3, 50 MHz): ꢀ 147.7, 129.3, 117.5,
113.4, 60.7, 31.2, 21.4; EIMS: m/z 292 (Mþ); Anal. calcd. for C20H24N2:
C, 82.19; H, 8.22; N, 9.59. Found: C, 81.98; H, 8.10; N, 9.86.
trans-N-Phenyl-N1-benzyl-1,2-cyclohexanediamine (k): M.p. 68–70ꢀC;
1
IR (KBr) 3295 cmÀ1; H NMR (CDCl3, 200 MHz): ꢀ 7.25 (m, 5H), 7.13
(m, 2H), 6.64 (m, 3H), 3.80 (J ¼ 13.3 Hz, 2H), 3.37 (br s, 1H, NH), 3.12
(ddd, J ¼ 10.2, 10.2, 3.6 Hz, 1H), 2.33 (ddd, J ¼ 9.9, 9.9, J ¼ 10.2, 10.2,
3.6 Hz, 1H), 2.33 (ddd, J ¼ 9.9, 9.9, 4.2 Hz, 1H), 2.18 (m, 2H), 2.10 (br s,
1H, NH), 1.7 (m, 2H), 1.23 (m, 3H), 1.1 (m, 1H); 13C NMR (CDCl3,
50 MHz), 148.2, 140.6, 129.2, 128.4, 128.1, 126.9, 117.7, 114.0, 60.8,
57.5, 50.7, 32.5, 31.4, 25.0, 24.6; EIMS: m/z 280 (Mþ); Anal. calcd. for
C19H24N2: C, 81.43; H, 8.57; N, 10.0. Found: C, 81.58; H, 8.49; N,
9.96.
N-Methyl-N-phenyl{3-benzylamino}butyl-2-amine (l): Viscous liquid,
IR (neat) 3300 cmÀ1; 1H NMR (CDCl3, 200 MHz): ꢀ 7.26 (m, 7H), 6.8 (d,
J ¼ 8.1 Hz, 2H), 6.76 (t, J ¼ 7.2 Hz, 1H), 3.81 (ABq, J ¼ 3.5 Hz, 2H), 3.67
(m, 1H), 2.73 (m, 1H), 2.50 (s, 3H), 2.30 (br s, 1H, NH), 1.14
(d, J ¼ 6.6 Hz, 3H), 1.02 (d, J ¼ 6.6 Hz, 3H); EIMS: m/z 268 (Mþ);
Anal. calcd. for C18H24N2; C, 80.60; H, 8.95; N, 10.45. Found: C,
80.44; H, 8.89; N, 10.58.

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Regioselective Ring Opening of Aziridines
ACKNOWLEDGMENTS
553
NRS is thankful to the Director IICT and Dr. J. S. Yadav for their
encouragement and CSIR New Delhi for providing fellowship.
REFERENCES
1. Reetz, M.T.; Jaeger, R.; Drewlies, R.; Hubel, M. Angew. Chem. Int.
Ed. Engl. 1991, 30, 103 and references cited therein.
2. Tanner, D. Angew. Chem. Int. Ed. Engl. 1994, 33, 599.
3. Dureault, A.; Tranchepain, I.; Depezay, J.C. J. Org. Chem. 1989,
54, 5324.
4. Tanner, D.; He, H.M. Tetrahedron 1992, 48, 6079.
5. Hudlicky, T.; Luna, H.; Price, J.D.; Rulin, F. J. Org. Chem. 1990,
55, 4683.
6. (a) Hudlicky, T.; Frazier, J.O.; Seoane, G.; Tiedje, M.; Seoane, A.;
Kwart, L.D.;Beal, C.J.Am. Chem.Soc.1986,108,3755;(b)Ploux,O.;
Caruso, M.; Chassaing, G.; Marquet, A. J. Org. Chem. 1988, 53,
3154; (c) Satoh, T.; Sato, T.; Oohara, T.; Yamakawa, K. J. Org.
Chem. 1989, 54, 3973; (d) Pearson, W.H.; Bergmeier, J.P. J. Org.
Chem. 1990, 55, 5719; (e) Davis, F.A.; Reddy, G.V. Tetrahedron
Lett. 1996, 37, 4349; (f ) Davis, F.A.; Liu, H.; Reddy, G.V.
Tetrahedron Lett. 1996, 37, 5473.
7. (a) For a general review of aziridine chemistry. See: Pearson, W.H.;
Lian, B.W.; Bergmeier, S.C. In comprehensive Hetrocyclic Chemistry
II; Katritzky, A.R., Rees, C.W., Scriven, E.F.V, Eds.; (b) Dauben,
P.; Dubois, L.; Dau, M.E.T.H.; Dodd, R.H. J. Org. Chem. 1995, 60,
2035; (c) da Zhang, Z.; Scheffold, R. Helv. Chim. Acta 1993, 76,
2602; (d) Bodenan, J.; Chanet-Ray, J.; Vessiere, R. Synthesis 1992,
288; (e) Sato, K.; Kozikowski, A.P. Tetrahedron Lett. 1989, 30,
4073; (f ) Nakajima, K.; Neya, M.; Yamada, S.; Okawa, K. Bull.
Chem. Soc. JPm. 1982, 55, 3049.
8. For Cr complex-catalyzed opening of aziridines with TMS azide,
see.: Leung, W.H.; YU, M.T.; Wu, M.-C.; Yeung, L.-L.
Tetrahedron Lett. 1996, 37, 891.
9. For opening of aziridine with TMSCN in the presence of lanthonoid
tricyanides, see; (a) Matsubara, S.; Kodama, T.; Utimoto, K.
Tetrahedron Lett. 1990, 31, 6379; (b) Osborn, H.M.I.; Sweeney,
J.B. Synlett 1994, 145.
10. For opening of aziridines with amines in the presence of Lewis acid
see; Sekar, G.; Singh, V.K. J. Org. Chem. 1999, 64, 2537.

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554
Swamy and Venkateswarlu
11. For rearrangement of acylaziridines to oxazolines using orthogonal
Lewis acid see: Ferrais, D.; Drury III W.J.; Cox, C.; Lectka, T.
J. Org. Chem. 1998, 63, 4568.
12. Meguro, M.; Asao, N.; Yamamoto, Y. Tetrahedron Lett. 1994,
35, 7395.
Received in the UK August 6, 2001