Synthesis of novel 5,6-dihydropyrrolo[2,1-a]isoquinolines via grob reaction between (E)-1,1,1-trifluoro-3-nitro-2-butene and 3,4-dihydroisoquinolines

Article abstract of DOI:10.1002/jhet.881

Uncatalyzed cycloaddition of 3,4-dihydroisoquinolines to (E)-1,1,1-trifluoro-3-nitro-2-butene via Grob reaction provide a simple one-step route to the 5,6-dihydropyrrolo[2,1-a]isoquinolines, which represent the basic structural framework of the antitumor active alkaloid crispine.

Full text of DOI:10.1002/jhet.881

856
Synthesis of Novel 5,6-Dihydropyrrolo[2,1-a]isoquinolines via
Grob Reaction between (E)-1,1,1-Trifluoro-3-nitro-2-butene and
3,4-Dihydroisoquinolines
Vol 49
a
a
a
*
Vladislav Y. Korotaev, Vyacheslav Y. Sosnovskikh, Alexey Y. Barkov,
Pavel A. Slepukhin,b and Yurii V. Shklyaevc
aDepartment of Chemistry, Ural State University, Ekaterinburg 620083, Russia
bInstitute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences,
Ekaterinburg 620041, Russia
cInstitute of Technical Chemistry, Ural Branch of the Russian Academy of Sciences,
Perm 614600, Russia
*
E-mail: Vyacheslav.Sosnovskikh@usu.ru
Received December 29, 2010
DOI 10.1002/jhet.881
View this article online at wileyonlinelibrary.com.
Uncatalyzed cycloaddition of 3,4-dihydroisoquinolines to (E)-1,1,1-trifluoro-3-nitro-2-butene via Grob
reaction provide a simple one-step route to the 5,6-dihydropyrrolo[2,1-a]isoquinolines, which represent the
basic structural framework of the antitumor active alkaloid crispine.
J. Heterocyclic Chem., 49, 856 (2012).
INTRODUCTION
to the corresponding 5,6-dihydropyrrolo[2,1-a]isoquino-
line derivatives [9]. Moreover, the reactivity of (E)-
1,1,1-trifluoro-3-nitro-2-butene (1) is nearly unexplored,
as only a handful of articles describing some reaction with
N- and O-nucleophiles is present in the literature [10].
A reaction involving the addition of enaminoesters to
nitroolefins followed by intramolecular displacement of
the nitro group by the amino group to yield pyrroles was
disclosed by Grob and coworkers [11]. This method makes
use of easily prepared reagents and is particularly suitable
for a combinatorial approach to the synthesis of substituted
pyrroles [9,12]. As imines and 3,4-dihydroisoquinolines
have been shown to react with b-nitrostyrene and 3-nitro-
2H-chromenes to give the corresponding pyrroles [8,13],
it was expected that Michael addition of 2a–f, including
dihydropapaverine (2d) and drotaverine (2e) (the hydro-
chloride of 2e is a well-known spasmolytic agent widely
used in medicine and known as No-Spa) to the nitrobutene
1, followed by ring closure and aromatization (Grob reaction)
could provide a direct route to 5,6-dihydropyrrolo[2,1-a]
isoquinolines 3a–f (Fig. 1).
In the last decades, considerable interest has been devoted
to the synthesis of partially fluorinated heterocycles, many
of which have used as agrochemicals and drugs [1]. How-
ever, reports on the use of polyfluoroalkylated nitroalkenes
as substrates for organic synthesis are very scarce [2],
although conjugated nitroolefins are versatile intermediates
in organic synthesis. The convertibility of the nitro group
into a variety of functional groups such as carbonyl (Nef
reaction), oxime, hydroxylamine, amine, and hydrogen
(via desamination reaction) enhances the usefulness of the
trihalomethylated nitroolefins in synthetic organic chemistry
[3]. In continuation of our studies on the chemical properties
of CX3-nitroalkenes (X = F and Cl), which turned out to be
highly reactive substrates in the hetero-Diels–Alder reaction
[4] and in reactions with some N-, O-, and C-nucleophiles
[5], we decided to investigate the reaction of (E)-1,1,1-
trifluoro-3-nitro-2-butene (1) with 1-methyl- and 1-benzyl-
3,4-dihydroisoquinolines 2, which are capable of reacting
with electrophilic substrates as C-nucleophiles or 1,3-C,
N-dinucleophiles via the enamine tautomeric form [6].
Although much attention has been paid to the chemistry
of 3,4-dihydroisoquinolines 2 [7], mainly due to their use
as excellent building blocks for the preparation of a variety
of complex heterocyclic compounds [6,8], there is only
one report on the reaction of ethyl-(6,7-dimethoxy-3,
4-dihydroisoquinolin-1(2H)-ylidene)acetate with 2-nitro-
1-phenylpropene and 1-nitro-1,2-diphenylethene leading
This heterocyclic system constitutes the basic structural
framework of the recently isolated two pyrrolo[2,1-a] isoqui-
noline alkaloids, crispine A and crispine B (Fig. 1), which in-
hibit the growth of some human cancer lines in vitro and show
a significant cytotoxic activity [14]. As a result of this potent
antitumor activity, various synthetic methods have been de-
veloped for the synthesis of crispine A, in both racemic [15]
and enantiomerically pure form [16], and many analogs have
© 2012 HeteroCorporation

July 2012
Synthesis of Novel 5,6-Dihydropyrrolo[2,1-a]isoquinolines via Grob Reaction between
(E)-1,1,1-Trifluoro-3-nitro-2-butene and 3,4-Dihydroisoquinolines
857
(Scheme 1). Compound 3 can serve as a basis for the
preparation of new physiologically active compounds.
For example, taking into account that the pyrrole ring of
3 can easily be reduced by the catalytic chemoselective hy-
drogenation [15(b)], this is a simple method for preparing
CF3-substituted crispine derivatives.
1
The structures of 3a–f were characterized by H, 19F,
and 13C NMR spectra and elemental analyses. For
1
compounds 3d,e, a characteristic feature of the H and
19F NMR spectra in CDCl3 is the presence of quartet at d
2.40–2.42 ppm for Me-3 group and quartet at d 109.9
5
ppm (HFB) for CF3 group with JH,F = 1.4 Hz. The 13C
NMR spectrum of 3d exhibited a quartet (4JC,F = 1.9 Hz)
at 10.4 ppm due to the Me-3 group, indicating that the
Me-3 and CF3 groups were spatially close to each other.
Finally, the structure of compound 3d was confirmed by
X-ray crystallographic analysis, which revealed that the
aromatic group on the pyrrole is almost orthogonal to the
rest of the relatively planar tricyclic system (Fig. 2). Keeping
1
this fact in mind and in making the H NMR assignments,
we have assumed that the ring current of the phenyl ring
attached at C-1 causes shielding of the proton at C-10
(d 6.41–6.44 ppm for 3d–f and 6.96 ppm for 3c). Note that
Figure 1. Starting materials for the synthesis of crispine derivatives.
1
the H NMR spectra of 3f displayed broad signals for the
been prepared [17]. In view of the unique biological proper-
ties displayed by crispines on one hand and by many fluo-
rine-containing heterocycles [1] on the other hand, it was
of interest to obtain a series of 5,6-dihydropyrrolo[2,1-a]
isoquinolines 3 with an electron-withdrawing CF3 group. In
this context, we regarded (E)-1,1,1-trifluoro-3-nitro-2-butene
(1) as a useful CF3-containing building block.
aromatic protons of the 3,4-(MeO)2C6H3 substituent and
for one of the four MeO groups. This phenomenon may be
attributed to the restricted rotation of the aryl moiety about
the C1-C10 bond leading to rotamer formation.
Interestingly, the reaction of 1,3,3,4,4,7-hexamethyl-
3,4-dihydroisoquinoline (2g) with nitrobutene 1 in toluene
Scheme 1
RESULTS AND DISCUSSION
We found that nitroalkene 1 reacted with dihydroisoqui-
nolines 2a–f in isobutanol at 80ꢀC for 0.5 h to produce
pyrrolo[2,1-a]isoquinolines 3a–f in 54–68% yields
(method A). As compounds 2a–f, especially 2d–f, are
prone to air oxidation, all operations should be performed
in an inert atmosphere. The synthesis of 3a–e has been also
achieved in high yields (67–80%) by the reaction of 1 with
2a–e in toluene at room temperature for 24 h (method B).
Under these conditions, the Michael adducts 4 could not be
isolated and underwent spontaneous cyclization to form the
fused pyrrole ring (Scheme 1, Table 1). The double bond of
1 is so reactive that no catalyst was necessary. However,
reactions of 1,1,1-trichloro-3-nitro-2-butene and 1-nitro-3,3,3-
trichloro(trifluoro)propenes with 3,4-dihydroisoquinolines
3a,b did not give the corresponding pyrrole derivatives and
only resinification was observed even at room temperature.
In accordance with the proposed mechanism [11(b)], the
Michael adduct A through intermediate B undergoes
intramolecular displacement of the nitro group by the NH
group; thus, affording pyrrolo[2,1-a]isoquinoline system
3 via elimination of water and hyponitrous acid H2N2O2
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

858
V. Y. Korotaev, V. Y. Sosnovskikh, A. Y. Barkov, P. A. Slepukhin, and Y. V. Shklyaev
Vol 49
Table 1
Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines 3a–f.
Yield (%)
Method A Method B
Isoquinoline
R1
R2
R3
R4
Pyrrole
2a
2b
2c
2d
2e
2f
H
H
H
Me
Me
Me
H
H
Me
Me
Me
Me
H
H
H
H
Me
MeO
MeO
EtO
MeO
3a
3b
3c
3d
3e
3f
68
56
55
60
65
54
80
71
73
67
68
–
3,4-(MeO)2C6H3
3,4-(EtO)2C6H3
3,4-(MeO)2C6H3
Method A: in isobutanol at 80ꢀC, 0.5 h.
Method B: in toluene at 20ꢀC, 12 h.
II spectrometers in CDCl3 with TMS and HFB as the internal
standards. IR spectra were recorded on Perkin–Elmer Spectrum
BX-II instrument as KBr disks. Elemental analyses were per-
formed on a Carlo Erba EA 1108 automatic analyzer at the
Microanalysis Services of the Institute of Organic Synthesis, Ural
Branch, Russian Academy of Sciences. Melting points are
uncorrected. All solvents used were dried and distilled per
standard procedures. Flash-chromatography was performed on
silica gel (LSL 5/40, Lachema). The starting (E)-1,1,1-trifluoro-
3-nitro-2-butene (1) and 1,3,3-trimethyl-3,4-dihydroisoquinolines
2a–c,g were prepared according to the described procedures
[10,18].
(method B) stopped at the initial stage to give the Michael
adduct 4g as a 53:44:3 mixture of two diastereomers
and pyrrole 3g, respectively, in 81% yield (19F NMR
spectrum). When this product was refluxed in isobutanol
for 3 h, 5,6-dihydropyrrolo[2,1-a]isoquinoline (3g) was
obtained in 55% yield (Scheme 2).
In conclusion, the reaction of 1,1,1-trifluoro-3-nitro-2-
butene with 3,4-dihydroisoquinolines provides a simple
and convenient procedure for the preparation of 5,6-dihy-
dropyrrolo[2,1-a]isoquinolines, which may be considered
as new tricyclic crispine derivatives. The resulting products are
of considerable interest as precursors in the synthesis of other
biologically and medicinally important organic materials.
General procedure for the synthesis of 5,6-dihydropyrrolo
[2,1-a]isoquinoline (3a–f).
Method A. A mixture of the
corresponding isoquinoline 2 (1.0 mmol) and nitrobutene 1
(0.16 g, 1.0 mmol) was heated at 80ꢀC in isobutanol (2 mL) for
0.5 h. After that, the mixture was concentrated under reduced
pressure, chromatographed on silica gel (eluted with
chloroform), and the solid formed was recrystallized from
isobutanol or hexane to give compound 3 as colorless powder.
Method B. A mixture of the corresponding isoquinoline 2 (1.0
mmol) and nitrobutene 1 (0.16 g, 1.0 mmol) was kept in toluene
at ∼20ꢀC for 12 h. After that, the mixture was concentrated under
reduced pressure, chromatographed on silica gel (eluted with
chloroform), and the solid formed was recrystallized from
isobutanol or hexane to give compound 3 as colorless powder.
EXPERIMENTAL
1H (400 MHz), 19F (376 MHz), and 13C (126 MHz) NMR
spectra were recorded on a Bruker DRX-400 and Bruker Avance
Scheme 2
Figure 2. Molecular structure of 3d (arbitrary numbering, thermal
ellipsoids at 50% probability).
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

July 2012
Synthesis of Novel 5,6-Dihydropyrrolo[2,1-a]isoquinolines via Grob Reaction between
(E)-1,1,1-Trifluoro-3-nitro-2-butene and 3,4-Dihydroisoquinolines
859
3,5,5-Trimethyl-2-(trifluoromethyl)-5,6-dihydropyrrolo[2,1-a]
Me-5, J = 6.6 Hz), 2.44 (s, 3H, Me-3), 2.71 (d, 1H, H-6a,
J = 15.3 Hz), 3.35 (dd, 1H, H-6b, J = 15.3, 5.8 Hz), 3.33,
3.85, 3.89 (all s, 3H, MeO), 3.70–3.85 (br s, 3H, MeO),
4.56 (quint, 1H, H-5, J = 6.2 Hz), 6.41 (s, 1H, H-10), 6.65
(s, 1H, H-7), 6.72ꢁ7.12 (m, 3H, Ar); 19F NMR (376 MHz,
CDCl3): d 111.2 (s, CF3). Anal. Calcd for C25H26F3NO4:
C, 65.07; H, 5.68; N, 3.04. Found: C, 64.92; H, 5.50; N, 3.22.
3,5,5,6,6,9-Hexamethyl-2-(trifluoromethyl)-5,6-dihydropyrrolo
[2,1-a]isoquinoline (3g). A mixture of isoquinoline 2g (0.37 g,
1.0 mmol) and nitrobutene 1 (0.16 g, 1.0 mmol) was refluxed
in isobutanol (2 mL) for 3 h. After that, the mixture was
concentrated under reduced pressure and chromatographed on
silica gel (eluted with chloroform). Yield 55%, colorless oil;
isoquinoline (3a). Yield 68% (method A), 80% (method B), mp
69–70ꢀC (hexane); IR (KBr) 1607, 1589, 1574, 1534, 1468,
1
1452, 1438 cmꢁ1; H NMR (400 MHz, CDCl3): d 1.57 (s, 6H,
2 Me), 2.54 (s, 3H, Me), 2.97 (s, 2H, CH2), 6.67 (s, 1H, H-1),
7.10–7.25 (m, 3H, H-7, H-8, H-9), 7.47 (d, 1H, H-10, J = 7.7 Hz);
19F NMR (376 MHz, CDCl3): d 106.3 (s, CF3). Anal. Calcd for
C16H16F3N: C, 68.81; H, 5.77; N, 5.01. Found: C, 68.99; H, 5.80;
N, 5.13.
3,5,5,8,9-Pentamethyl-2-(trifluoromethyl)-5,6-dihydropyrrolo
[2,1-a]isoquinoline (3b). Yield 56% (method A), 71% (method B),
mp 119ꢁ120ꢀC (hexane); IR (KBr) 1596, 1571, 1535, 1452, 1440
1
cmꢁ1; H NMR (400 MHz, CDCl3): d 1.56 (s, 6H, 2 Me), 2.24,
1
2.26, 2.52 (all s, 3H, Me), 2.90 (s, 2H, CH2), 6.61 (s, 1H, H-1),
6.88 (s, 1H, H-7), 7.25 (s, 1H, H-10); 19F NMR (376 MHz,
CDCl3): d 106.4 (s, CF3). Anal. Calcd for C18H20F3N: C, 70.34;
H, 6.56; N, 4.56. Found: C, 70.09; H, 6.70; N, 4.80.
IR (KBr) 1614, 1592, 1571, 1536, 1487, 1442 cmꢁ1; H NMR
(400 MHz, CDCl3): d 1.04, 1.16, 1.47, 1.84 (all br s, 12H, 4
Me), 2.34 (s, 3H, Me-9), 2.53 (s, 3H, Me-3), 6.64 (s, 1H, H-1),
6.99 (d, 1H, H-8, J = 7.9 Hz), 7.22 (d, 1H, H-7, J = 7.9 Hz),
7.30 (s, 1H, H-10); 19F NMR (376 MHz, CDCl3): d 106.6
(s, CF3). Anal. Calcd for C19H22F3N: C, 71.01; H, 6.90;
N, 4.36. Found: C, 69.85; H, 6.74; N, 4.43.
8,9-Dimethoxy-3,5,5-trimethyl-2-(trifluoromethyl)-5,6-
dihydropyrrolo[2,1-a]isoquinoline (3c). Yield 55% (method A),
73% (method B), mp 104ꢁ105ꢀC (hexane); IR (KBr) 1612,
1574, 1538, 1500, 1437 cmꢁ1
;
1H NMR (400 MHz, CDCl3):
3,3,4,4,7-Pentamethyl-1-[3-nitro-2-(trifluoromethyl)butyl]-3,4-
dihydroisoquinoline (4g). This compound was prepared from
1,3,3,4,4,7-hexamethyl-3,4-dihydroisoquinoline (2g) and nitrobutene
1 according to the method B. Yield 81%, yellow oil; IR (KBr)
d 1.57 (s, 6H, 2 Me), 2.53 (s, 3H, Me-3), 2.90 (s, 2H, CH2),
3.89 (s, 3H, MeO), 3.91 (s, 3H, MeO), 6.54 (s, 1H, H-1),
6.63 (s, 1H, H-7), 6.96 (s, 1H, H-10); 19F NMR (376 MHz,
CDCl3): d 106.4 (s, CF3). Anal. Calcd for C18H20F3N: C, 63.71;
H, 5.94; N, 4.13. Found: C, 63.75; H, 6.09; N, 4.02.
1
1642, 1612, 1559, 1442, 1392, 1376, 1364 cmꢁ1; H NMR (400
MHz, CDCl3): d major isomer (55%): 1.0–1.2 (m, 12H, 4 Me),
1.62 (d, 3H, Me, J = 7.0 Hz), 2.38 (s, 3H, Me), 2.91 (dd, 1H,
CHH, J = 17.2, 8.5 Hz), 3.16 (dd, 1H, CHH, J = 17.2, 2.9 Hz),
4.22ꢁ4.34 (m, 1H, CHMe), 4.98–5.06 (m, 1H, CHCF3),
7.18ꢁ7.30 (m, 3H, Ar), minor isomer (45%): 1.0–1.2 (m, 12H, 4
Me), 1.65 (d, 3H, Me, J = 7.1 Hz), 2.38 (s, 3H, Me), 3.05 (d, 2H,
CH2, J = 5.9 Hz), 4.22ꢁ4.34 (m, 1H, CHMe), 4.87–4.95 (m, 1H,
CHCF3), 7.18ꢁ7.30 (m, 3H, Ar); 19F NMR (376 MHz, CDCl3):
d major isomer (53%): 94.6 (d, CF3, 3JF,H = 9.6 Hz), minor isomer
(44%): 93.2 (d, CF3, 3JF,H = 9.2 Hz), 3g (3%): 106.6 (s, CF3).
Crystal data for 3d. Diffraction data were collected at 295 K
on an Xcalibur 3 automatic single-crystal diffractometer (graphite-
monochromated MoKa radiation, o-scans). The structures were
solved by direct methods and refined by the full-matrix least-
squares method using the SHELX-97 program package [19]. The
H atoms were located geometrically using the riding model.
Crystal data: C24H24F3NO4, M = 447.44, triclinic, space group
P-1, a = 8.4754 (12) Å, b = 11.3587 (10) Å, c = 11.8318 (7) Å,
a = 87.090 (6)ꢀ, b = 83.664 (8)ꢀ, g = 76.787 (10)ꢀ, V = 1101.73 (19)
Å3, Z = 2, rcalcd = 1.349 g/cm3, m = 0.108 mmꢁ1, F(0 0 0) = 468.
Final R = 0.0466, wR2 = 0.1244, S = 1.008 for 320 parameters and
9934 reflections, 5165 unique [R(int) = 0.0163], of which 2278
with I > 2r(I).
1-(3,4-Dimethoxyphenyl)-8,9-dimethoxy-3-methyl-2-
(trifluoromethyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline (3d). Yield
60% (method A), 67% (method B), mp 122ꢁ123ꢀC (isobutanol);
IR (KBr) 1610, 1579, 1568, 1544, 1517, 1496, 1469 cmꢁ1 1H
;
5
NMR (400 MHz, CDCl3): d 2.42 (q, 3H, Me-3, JH,F = 1.4
Hz), 3.02 (t, 2H, CH2, J = 6.5 Hz), 3.32, 2.83, 3.85, 3.90 (all s,
3H, Me), 3.97 (t, 2H, CH2N, J = 6.5 Hz), 6.42 (s, 1H, H-10),
6.66 (s, 1H, H-7), 6.90ꢁ6.95 (m, 3H, Ar); 19F NMR (376
5
MHz, CDCl3): d 109.9 (q, CF3, JF,H = 1.4 Hz); 13C NMR
4
(126 MHz, CDCl3): d 10.4 (q, Me-3, JC,F = 1.9 Hz), 28.9,
2
40.9, 55.1, 55.87, 55.93, 56.0, 107.5, 110.7 (q, C-2, JC,F = 32.8
3
Hz), 110.9, 111.3, 114.2, 118.1 (q, C-1, JC,F = 2.2 Hz), 121.7,
1
123.2, 123.6, 124.9 (q, CF3, JC,F = 268.0 Hz), 125.7, 127.4
3
(q, C-3, JC,F = 3.4 Hz), 128.0, 147.1, 147.5, 148.3, 148.9.
Anal. Calcd for C24H24F3NO4: C, 64.42; H, 5.41; N, 3.13.
Found: C, 64.51; H, 5.44; N, 3.08.
1-(3,4-Diethoxyphenyl)-8,9-diethoxy-3-methyl-2-(trifluoromethyl)-
5,6-dihydropyrrolo[2,1-a]isoquinoline (3e). Yield 65% (method
A), 68% (method B), mp 137ꢁ138ꢀC (isobutanol); IR (KBr) 1607,
1
1568, 1576, 1543, 1515, 1494, 1475 cmꢁ1; H NMR (400 MHz,
CDCl3): d 1.15, 1.39, 1.41, 1.46 (all t, 3H, Me, J = 7.0 Hz), 2.40
5
(q, 3H, Me-3, JH,F = 1.4 Hz), 2.98 (t, 2H, CH2, J = 6.5 Hz),
3.53 (q, 2H, CH2O, J = 7.0 Hz), 3.95 (t, 2H, CH2N, J = 6.5 Hz),
4.05 (q, 4H, 2 CH2O, J = 7.0 Hz), 4.12 (q, 2H, CH2O, J = 7.0
Hz), 6.44 (s, 1H, H-10), 6.66 (s, 1H, H-7), 6.85ꢁ6.91 (m, 3H,
Crystallographic data for compound 3d (CCDC deposition num-
ber 804622) have been deposited at the Cambridge Crystallographic
Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.
5
Ar); 19F NMR (376 MHz, CDCl3): d 109.9 (q, CF3, JF,H = 1.4
Hz). Anal. Calcd for C28H32F3NO4: C, 66.79; H, 6.41; N, 2.78.
Found: C, 66.70; H, 6.55; N, 2.76.
Acknowledgments. This work was financially supported by the RFBR
1-(3,4-Dimethoxyphenyl)-8,9-dimethoxy-3,5-dimethyl-2-
(trifluoromethyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline (3f). This
compound was prepared from 1-(3,4-dimethoxybenzyl)-6,7-
dimethoxy-3-methyl-3,4-dihydroisoquinoline (0.39 g, 1.0 mmol)
and nitrobutene 1 (0.16 g, 1.0 mmol) in the presence of Et3N
(0.12 g, 1.2 mmol) according to the method A. Yield 54%, mp
129ꢁ130ꢀC (isobutanol); IR (KBr) 1610, 1564, 1543, 1517,
(grant 10-03-00138) and the Presidium program of the RAS N 21.
REFERENCES AND NOTES
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1
1494, 1466 cmꢁ1; H NMR (400 MHz, CDCl3): d 1.19 (d, 3H,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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V. Y. Korotaev, V. Y. Sosnovskikh, A. Y. Barkov, P. A. Slepukhin, and Y. V. Shklyaev
Vol 49
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet