Allylboration of functionalized isoquinolines

Article abstract of DOI:10.1016/S0022-328X(02)01406-7

Functionalized isoquinolines react with triallylborane to produce 1,3-diallylated 1,2,3,4-tetrahydroisoquinolines 1-8 with excellent chemo- and stereoselectivity. In these conditions 4-bromoisoquinoline was converted into tricyclic aziridine 10. Synthesis

Full text of DOI:10.1016/S0022-328X(02)01406-7

Journal of Organometallic Chemistry 657 (2002) 123ꢀ128
/
www.elsevier.com/locate/jorganchem
Allylboration of functionalized isoquinolines
Fedor V. Pastukhov a, Ilia V. Yampolsky a, Yuri N. Bubnov a,b,
*
a A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russia
b N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russia
Received 3 September 2001; accepted 12 March 2002
Abstract
Functionalized isoquinolines react with triallylborane to produce 1,3-diallylated 1,2,3,4-tetrahydroisoquinolines 1ꢀ
/8 with
excellent chemo- and stereoselectivity. In these conditions 4-bromoisoquinoline was converted into tricyclic aziridine 10. Synthesis of
monoallylated tetrahydroisoquinolines using allyldipropylborane and reduction with NaBH4 was also developed. # 2002 Elsevier
Science B.V. All rights reserved.
Keywords: Isoquinolines; Boranes; Allylation; Allylboration; Stereoselectivity; Aziridines
1. Introduction
Recently, we have found that isoquinolines react
easily with allylzinc bromide giving either A or benzoi-
soquinuclidine derivative depending on the reaction
conditions [11].
In order to expand the scope of application for the
reaction of isoquinoline with triallylborane, we decided
to introduce a range of functionalized isoquinolines into
it.
1,2-Addition of organometallic reagents to the CÄ
double bond is a classical reaction widely used in
organic synthesis [1,2]. Thus, allylboration [2ꢀ7] of
imines is an accustomed method for synthesis of
butenylamines of diverse constitution.
Several aromatic nitrogen heterocycles e. g. quinolines
and phenanthridine react with allylboranes in a way
analogous to imines to give the products of addition to
/
N
/
the CÄ
/
N bond. Deboronation of aminoboranes formed
95%) and 5-
2. Results and discussion
leads to 2-allyl-1,2-dihydroquinolines (85ꢀ
/
allyl-5,6-dihydrophenanthridine [8], respectively. Isoqui-
noline is also easily allylborated with triallylborane
(All3B) [9]. Subsequent action of alcohol (1 h, 20 8C)
and alkali solution afford trans-1,3-diallyl-1,2,3,4-tetra-
hydroisoquinoline A. It should be noted, that in this
unusual transformation the alcohol is an essential
reagent, but not just a solvent.
Isoquinolines bearing large variety of substituents are
transformed into trans-1,2-diallyl-1,2,3,4-tetrahydroiso-
quinolines under the action of allylic boranes. These
reactions proceed in mild conditions, with high chemos-
electivity.
Such substituents as halogen, amino-group, and even
easily reduced by allylboranes cyano- and nitro-groups
are left unchanged under the experimental conditions.
It is known that aliphatic and aromatic nitriles readily
react with triallylborane giving (after work-up) a,a-
diallylamines [4]. We carried out the reaction of 5-
Allylboration is also a key step in synthesis of
unsymmetrically substituted trans-1-R-3-allyl-1,2,3,4-
tetrahydroisoquinolines (Rꢁ
/
Alk, Ar) from isoquino-
line, RLi and All3B [10].
All the above mentioned reactions proceed with allylic
rearrangement seemingly via six-membered chair-like
transition state [7].
cyanoisoquinoline with All3B at ꢂ35 8C and isolated
/
only the product of isoquinoline ring allylboration 2.
Aromatic nitro-compounds react with All3B at 80 8C
radically, giving the products of partial reduction of
nitro-group [12]. At ꢂ
/
35 8C the reaction of 5-nitroiso-
* Corresponding author. Fax: ꢃ
/
7-95-135-5085.
E-mail address: dir@ineos.ac.ru (Y.N. Bubnov).
quinoline with 1 equivalent of All3B does not involve
0022-328X/02/$ - see front matter # 2002 Elsevier Science B.V. All rights reserved.
PII: S 0 0 2 2 - 3 2 8 X ( 0 2 ) 0 1 4 0 6 - 7

124
F.V. Pastukhov et al. / Journal of Organometallic Chemistry 657 (2002) 123ꢀ128
/
nitro-group, and compound 3 was isolated after debor-
onation in 95% yield.
logous to C, which undergoes rearrangement into imine
under the action of alcohol. Dipropyl(ethoxy)borane
formed is unreactive to imines (unlike diallyl(alkox-
y)borane), so the intermediate imine can be introduced
into the reaction with NaBH4 to produce (after debor-
onation) the corresponding amine 9.
Tris(2-methyl-2-propenyl)borane (trimethallylborane)
reacts with isoquinoline analogously to All3B giving the
corresponding trans-1,3-dimethallyl-1,2,3,4-tetrahydroi-
soquinolines (7 and 8) with high stereoselectivity
(Scheme 1).
The most interesting result was obtained when 4-
bromoisoquinoline was consequently treated with All3B,
A possible mechanism of allylboration of isoquino-
lines is shown in Scheme 2.
i
and the mixture PrOHꢀ
/Et3N (Scheme 4).
In the first step, the allylborane addition to the 1,2 CÄ
/
N bond of isoquinoline takes place. In the second, key
step, the stable intermediate C undergoes rearrangement
under the action of electrophile, such as isopropyl
alcohol. In the course of this rearrangement enamino-
borane C is transformed into iminoborane D, in which
the imino-function is immediately allylborated [7] re-
sulting in E. The deboronation method used in the last
step of this one-pot procedure depends on the substi-
tuents in the isoquinoline ring. For example, the cyano-
group is labile to the aqueous NaOH, so in case of 5-
cyanoisoquinoline the mild deboronation procedure
using diethanolamine was used.
Basing on the above mechanism, we decided to carry
out monoallylation of 5-bromoisoquinoline with allyl-
dipropylborane (Scheme 3).
On the first stage of this reaction allyldipropylborane
adds to 5-bromoisoquinoline forming an enamine ana-
Scheme 3. Synthesis of monoallylated 1,2,3,4-tetrahydroisoqionoline.
Scheme 1. Chemoselective allylboration of functionalized isoquinolines.
Scheme 2. Possible mechanism of allylboration of isoquinolines.

F.V. Pastukhov et al. / Journal of Organometallic Chemistry 657 (2002) 123ꢀ
/128
125
treatment of 3,5-dibromopyridine with triallylborane
and Et3Nꢀi
PrOH afforded bicyclic aziridine 11 as a
mixture of diastereomers 1:1 in 92% yield (Scheme 5).
/
3. Experimental
3.1. General remarks
All operations with organoboron compounds were
carried out in a dry argon atmosphere. Absolute THF,
benzene and iPrOH were used. NMR 1H and 13C
spectra were recorded on Bruker AC-200P and AM-
300 instruments. Mass-spectra were obtained on a
VARIAN-MAT instrument.
Scheme 4. Aziridine formation from 4-bromoisoquinoline.
3.2. trans-1,3-Diallyl-5-bromo-1,2,3,4-
tetrahydroisoquinoline (4) (general procedure)
Triallylborane (4.6 ml, 26 mmol) was added to the
solution of 5-bromoisoquinoline (5.0 g, 24 mmol) in 25
ml benzene with stirring. The dark-red coloration of the
reaction mixture appeared for several seconds, and then
disappeared. The solution was refluxed for 30 min,
cooled to 0 8C, worked up with isopropanol (6.2 ml, 72
mmol) and refluxed for 2 h. Then 5 M NaOH was added
and the mixture was vigorously stirred until complete
deboronation (no green coloration of flame) of the
Scheme 5. Aziridine formation from 2,5-dibromopyridine.
organic layer (:
separated and the aqueous layer extracted with diethyl
ether (3ꢄ10 ml). Combined organic extracts were dried
with K2CO3 and concentrated. Distillation (136ꢀ
/
30 min). The organic layer was
The intermediate b-bromoamine F formed after
diallylboration undergoes cyclization into aziridine 10
under the action of base. As 1- and 3-allylic groups are
always in trans-position to each other, 10 is a mixture of
only two diastereomers in a 1:3 ratio (NMR), differing
in orientation of the aziridine ring relative to 1-allylic
group.
3-Bromopyridine presents a system, analogous to 4-
bromoisoquinoline. However, 3-bromopyridine reacts
with All3B giving trans-2,5-diallyl-3-bromo-1,2,5,6-tet-
rahydropyridine [13]. At the same time, consequent
/
/
137 8C/0.5 Torr) gave 4 (6.51 g, 92%).
3.3. trans-1,3-Diallyl-5-amino-1,2,3,4-
tetrahydroisoquinoline (1)
Two equivalents of triallylborane were used. Yield:
95%, melting point (m.p.) 89ꢀ90 8C.
/
Table 1
Experimental data
Compound
X1
X2
X3
R
Yield (%)
B.p. (8C Torrꢂ1
)
M.p. (8C)
n2D0
1
2
NH2
CN
NO2
Br
H
H
H
H
Br
H
H
H
H
H
H
H
Br
Br
H
H
H
95
86
95
92
82
75
95
90
61
90
ꢀ
ꢀ/
ꢀ/
/
89.5ꢀ
62ꢀ63
68ꢀ69
169ꢀ
170a
62ꢀ63
215ꢀ
177ꢀ
206ꢀ
214ꢀ
/
90
ꢀ
ꢀ/
ꢀ/
/
H
/
3
H
/
4
H
136ꢀ
/
137/0.5
/
1.5714
5
Br
Br
H
ꢀ/
/
ꢀ/
6
H
168ꢀ
142ꢀ
153ꢀ
123ꢀ
95ꢀ
/
170/0.5
143/0.5
154/0.5
125/0.5
/
216a
179a
207a
215a
1.6134
1.5382
1.5590
7
H
Br
Me
Me
/
/
8
/
/
9
10
/
/
ꢀ/
/
96/0.5
ꢀ/
1.5429
a
Melting point given for hydrochloride.

126
F.V. Pastukhov et al. / Journal of Organometallic Chemistry 657 (2002) 123ꢀ128
/
Table 2
Elemental analysis data
3.4. trans-1,3-Diallyl-5-cyano-1,2,3,4-
tetrahydroisoquinoline (2)
Compound %C Calc./Found %H Calc./Found %N Calc./Found
To the solution of 5-cyanoisoquinoline (1.0 g, 6.5
mmol) in 20 ml THF triallylborane (1.2 ml, 6.7 mmol,
1
78.90/78.95
80.63/80.69
69.74/69.71
61.65/61.62
40.04/39.94
44.20/44.30
84.59/84.45
63.75/63.79
49.94/49.93
85.26/85.40
8.83/8.92
7.61/7.69
7.02/7.09
6.21/6.30
3.58/3.64
4.45/4.50
9.60/9.65
6.92/6.97
5.24/5.30
8.11/8.08
12.27/12.23
11.75/11.69
10.84/10.74
4.79/4.68
3.11/3.07
3.44/3.49
5.80/5.63
4.37/4.20
4.85/4.78
6.63/6.07
2
1.03 equivalents) was added at ꢂ
The mixture was allowed to warm to room temperature
(r.t.), after 30 min it was cooled to ꢂ10 8C and
/
35 8C with stirring.
3
4
/
5
6*HCl
isopropanol (1.6 ml, 20 mmol) was added. The solution
stayed for 12 h at r.t., then worked up with diethano-
lamine (7.8 mmol) and the mixture was left at r.t. for 10
h. The crystalline solid (borate complex with diethano-
lamine) was filtered off and washed with hot hexane.
The combined filtrate was concentrated in vacuo,
diluted with hexane and filtered from solid borate
complex. Hexane was removed in vacuo and the solid
obtained was recrystallized from hexane, giving 2 (1.3 g,
7
8
9*HCl
10
Table 3
Mass-spectroscopic data
Compound
(Mr)
Mass spectrum m/z (Irel, %)
86%) as yellow needles (m.p. 62ꢀ63 8C).
/
1 (228)
2 (238)
3 (258)
4 (292)
5 (450)
7 (241)
8 (320)
10 (211)
228(2); 187(100); 158(6); 145(86); 129(15); 117(11);
91(8); 72(14); 58(24); 43(34)
3.5. trans-1,3-Diallyl-5-nitro-1,2,3,4-
tetrahydroisoquinoline (3)
197(19); 187(16); 154(15); 144(26); 58(64); 43(100);
41(10)
217(100); 187(9); 176(18); 175(18); 170(21); 159(80);
143(27); 129(60); 58(18); 43(29)
Compound 3 was obtained analogously to 2, debor-
onation analogous to 4. Yield: 95%, m.p. 68ꢀ69 8C.
/
252, 250(100); 210, 208(97); 211(30); 170(12); 153(13);
143(100; 130(72); 129(68); 58(59); 41(55)
409(100); 368(32); 287(7); 208(9); 130(7); 58(66);
43(100)
3.6. 1-Allyl-5-bromo-1,2,3,4-tetrahydroisoquinoline (9)
241(1); 186(63); 144(32); 130(63); 115(30); 103(45);
91(40); 76(37); 55(40); 41(45)
To the solution of 5-bromoisoquinoline (6.0 g, 29
mmol) in 30 ml THF allyldipropylborane (5.2 ml, 29
mmol) was added dropwise with stirring. The mixture
was stirred 1 h at r.t., then NaBH4 (2.2 g, 58 mmol) and
absolute ethanol (50 ml) were added. After stirring for 5
h, 10 ml H2O was added and the mixture was refluxed
266, 294(96); 210, 208(100); 170(17); 168(14); 143(12);
129(60); 115(11); 55(14); 40(21)
211(42), 210(47), 184(13), 170(100), 167(83), 157(15),
155(37), 143(43), 130(54), 128(40), 117(39), 58(44),
43(55), 41(49)
Table 4
13C chemical shifts (ppm)
Compound
1
3
4
CAromÃH
CArom. quaternary
9, 9?
10, 10?
11, 11?
12, 12?
1
2
3
4
5
6
7
8
9
54.9 45.2 30.5 112.3, 117.9, 125.8
54.7 45.1 34.3 125.9, 130.8, 131.4
55.1 44.9 32.8 122.5, 125.9, 131.7
55.2 45.7 36.5 126.1, 126.8, 130.1
119.2, 139.0, 143.9
112.5, 138.3, 139.9
129.9, 141.3, 149.2
125.4, 134.1, 140.9
40.6, 41.1 117.1, 117.6 134.9, 135.8
40.8, 40.6 118.3, 118.9 134.4, 134.9
40.7, 40.9 118.1, 118.8 134.4, 134.8
ꢀ
ꢀ/
ꢀ/
ꢀ/
ꢀ/
ꢀ/
/
40.9
118.0, 118.5 134.8, 135.3
a
57.5 44.8 41.0 134.3
56.0 45.1 41.0 131.4
123.6, 124.9, 128.2, 135.2, 142.4 36.0, 36.4 118.4, 118.5 134.3*, 134.8
121.7, 124.7, 136.4, 140.1 36.2, 36.7 118.2, 118.3 134.4, 135.0
45.4* 113.4, 113.6 142.0, 142.7 22.0, 22.4
45.0, 45.3 113.6, 113.9 141.7, 142.2 21.9, 22.3
40.3 118.1 135.1
42.2, 42.3 116.0, 117.0 135.1, 135.8
a
52.8 43.7 36.4 125.5, 125.9, 127.0, 128.8 134.6, 138.5
53.1 43.5 37.1 126.2, 126.7, 130.0
55.1 40.4 30.6 125.1, 126.8, 130.0
125.2, 134.4, 141.1
125.7, 135.0, 141.3
ꢀ/
ꢀ/
10 major isomer 64.0 47.7 26.0 122.1, 123.5, 127.0, 127.1 138.0, 146.2
a
Merged peaks.

Table 5
1H Chemical shifts (ppm) and coupling constants (Hz)
Compound
1
2
3
4
4?
1.9ꢀ
3.05dd Jꢁ4.1; 2.65dd Jꢁ17.3;
5
6
7
8
9, 9?
10, 10? 11, 11? 12, 12?
1
4.0dd Jꢁ4; 10 2.05br. s 3.15m
1.9ꢀ
/
2.6m
/2.6m
3.55br. s
(NH2)
6.55m
7.0m
6.55m
1.9ꢀ
/
5.15m
5.15m
5.15m
5.15m
5.15m
5.25m
4.85m
4.85m
5.3m
5.85m
5.85m
5.9m
5.9m
5.8m
5.9m
ꢀ
/
2.6m
2
4.05dd Jꢁ4.2; 2.05br. s 3.15m
9.8
ꢀ
/
7.5d Jꢁ7.7
7.8d Jꢁ7.7
7.4d Jꢁ7.3
7.75s
7.2ꢀ
/
7.4m
7.2ꢀ
7.4m
/
2.1ꢀ
2.55m
2.1ꢀ
2.6m
2.1ꢀ
2.45m
1.9ꢀ
2.5m
2.6ꢀ
3.1m
2.0ꢀ
2.7m
2.0ꢀ
/
ꢀ/
17.3
10.3
3
4.15dd Jꢁ4.0; 2.0br. s
9.9
3.05m
3.15m
3.0dd Jꢁ3.7;
17.3
2.8dd Jꢁ10.3;
17.3
ꢀ
/
7.3m
7.4d
Jꢁ7
7.05m
/
ꢀ/
4
4.05dd Jꢁ4;
9.9
2.05s
2.85dd Jꢁ4.1; 2.55dd Jꢁ9.6;
16.9 16.9
ꢀ
/
7.05m
/
ꢀ/
5
4.25dd Jꢁ2; 11 1.9ꢀ
/
2.5m 3.4m
2.85dd Jꢁ4.4; 2.65d Jꢁ14.3
17.6
ꢀ
/
ꢀ
/
ꢀ
/
/
ꢀ/
6*HCl
4.85m
9.45;
10.92s
4.20dd Jꢁ2.3; 2.0ꢀ
10.8
4.15dd Jꢁ2.7; 2.0ꢀ
3.65br. s 3.2dd Jꢁ5.5;
18.0
2.6ꢀ/3.1m
ꢀ
/
7.35AB
Jꢁ8.5
7.1m
7.35AB
Jꢁ8.5
7.1m
ꢀ
/
/
ꢀ/
7
/
2.7m 3.2m
2.75dd Jꢁ3.3; 2.0ꢀ
16.2
2.85dd Jꢁ3.6; 2.55dd Jꢁ11.1;
/2.7m
7.1m
7.1m
7.0m
7.1m
/
ꢀ/
1.80s,
1.87s
1.78s,
1.85s
8
/
3.2m
ꢀ
/
7.4dd Jꢁ1.7; 7.0m
7.2
/
ꢀ/
10.8
2.45m
17
14.0
2.45m
9*HCl
4.6s
9.7; 9.92s 3.4;
3.62s
3.2m
ꢀ/
ꢀ
/
7.55dd
Jꢁ1.5; 7
7.0ꢀ
7.1m
7.0ꢀ7.4m
2.9m
5.85m
ꢀ/
10 (2 diastereo-
4.05m
ꢀ
/
3.57m
1.5ꢀ
/
2.7m
ꢀ/
7.0ꢀ
/7.4m
/
7.4m
/
7.0ꢀ
/
1.5ꢀ
/
4.9ꢀ
/
5.6ꢀ
/
ꢀ/
mers)
7.4m
2.7m
5.2m
6.0m

128
F.V. Pastukhov et al. / Journal of Organometallic Chemistry 657 (2002) 123ꢀ128
/
(c) Y. Yamamoto, T. Komatsu, K. Maruyama, J. Org. Chem. 50
(1985) 3115.
for 30 min. Then 6 M NaOH (50 ml) and H2O2 30% (15
ml) were consequently added with stirring. The reaction
mixture was stirred until complete deboronation of the
organic layer (flame probe). Standard extractive workup
and distillation in vacuo gave 4.4 g (61%) of 9 as a
[4] (a) Yu.N. Bubnov, V.S. Bogdanov, B.M. Mikhailov, Zhurnal.
Obschei. Khimii. Russ. 38 (1968) 260;
(b) Yu.N. Bubnov, V.S. Bogdanov, B.M. Mikhailov, Chem.
Abstr. 69 (1968) 52200j.
[5] (a) L.I. Lavrinovich, A.V. Ignatenko, Yu.N. Bubnov, Izv. Akad.
Nauk. Ser. Khim. (1992) 2597;
viscous colorless oil (boiling point (b.p.) 123ꢀ
0.5 Torr). For further purification the product was
transformed into hydrochloride, m.p.ꢁ214ꢀ215 8C
from EtOAcꢀMeOH.
/
125 8C/
(b) L.I. Lavrinovich, A.V. Ignatenko, Yu.N. Bubnov, Bull. Russ.
Acad. Sci. Div. Chem. Sci. 41 (1992) 2051 (English Translation);
(c) M.E. Gurski, S.B. Golovin, A.V. Ignatenko, Yu.N. Bubnov,
Izv. Akad. Nauk. Ser. Khim. (1992) 2198;
/
/
/
(d) M.E. Gurski, S.B. Golovin, A.V. Ignatenko, Yu.N. Bubnov,
Bull. Russ. Acad. Sci. Div. Chem. Sci. 41 (1992) 1724 (English
Translation);
3.7. Aziridine 10 (mixture of diastereomers)
To the solution of 4-bromoisoquinoline (2.0 g, 14
mmol) in 20 ml of hexaneꢀTHF mixture 1:1, triallylbor-
(e) M.E. Gurski, T.V. Potapova, Yu.N. Bubnov, Izv. Akad.
Nauk. Ser. Khim. (1998) 1450;
/
ane (2.6 ml, 15 mmol) was added dropwise with stirring.
After 1 h stirring, the mixture of 1.6 ml NEt3 and 2.5 ml
iPrOH was added, and the resulting solution was heated
at 45 8C for 5 h. Deboronation procedure analogous to
4, extractive workup and distillation gave 2.7 g (90%) of
(f) M.E. Gurski, T.V. Potapova, Yu.N. Bubnov, Russ. Chem.
Bull. 47 (1998) 1410 (English Translation).
[6] (a) Sh. Itsuno, K. Watanade, K. Ito, A.A. El-Shehaway, A.
Sharhan, Angew. Chem. Int. Ed. Engl. 36 (1997) 109;
(b) A.A. El-Shehaway, M.Y. Abdelaal, K. Watanade, K. Ito, Sh.
Itsuno, Tetrahedron: Asymmetry 8 (1997) 1731.
[7] (a) Yu.N. Bubnov, Pure Appl. Chem. 66 (1994) 235;
(b) Yu.N. Bubnov, in: G.W. Kabalka (Ed.), Current Topics in the
Chemistry of Boron, The Royal Society of Chemistry, Thomas
Graham House, Cambridge, 1994, p. 44.
10 (b.p. 95ꢀ
/
96 8C/0.5 Torr) (Tables 1ꢀ5).
/
Acknowledgements
[8] (a) Yu.N. Bubnov, S.V. Evchenko, A.V. Ignatenko, Izv. Akad.
Nauk. Ser. Khim. (1992) 2815;
We thank Russian Foundation for Basic Research
(grants 00-15-97378, 02-03-32248 and 01-03-06323), and
Russian Ministry of Science and Technology (grant 402-
19-/22.3/23.1(00)-R-D01) for financial support, and
A.V. Ignatenko for NMR studies.
(b) Yu.N. Bubnov, S.V. Evchenko, A.V. Ignatenko, Bull. Russ.
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