Synthesis of new quinoline derivatives

Article abstract of DOI:10.1080/00397910600943568

The synthesis of some new functionalized quinolyl derivatives has been described, based on the 1,3-dipolar cycloaddition of an azomethine ylide, generated from sarcosine or N-benzylglycine and paraformaldehyde, to 2-chloro-3-quinolinecarbaldehydes. Copyright Taylor & Francis Group, LLC.

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Synthesis of New Quinoline Derivatives
Judit Tóth a , Gábor Blaskó b , András Dancsó b , László Tőke a & Miklós
Nyerges a
a Research Group of the Hungarian Academy of Sciences, Department of
Organic Chemical Technology, Technical University of Budapest, Budapest,
Hungary
b EGIS Pharmaceuticals Ltd., Budapest, Hungary
Version of record first published: 24 Nov 2006
To cite this article: Judit Tóth, Gábor Blaskó, András Dancsó, László Tőke & Miklós Nyerges (2006): Synthesis
of New Quinoline Derivatives, Synthetic Communications: An International Journal for Rapid Communication
of Synthetic Organic Chemistry, 36:23, 3581-3589
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Synthetic Communicationsw, 36: 3581–3589, 2006
Copyright # Taylor & Francis Group, LLC
ISSN 0039-7911 print/1532-2432 online
DOI: 10.1080/00397910600943568
Synthesis of New Quinoline Derivatives
´
Judit Toth
Research Group of the Hungarian Academy of Sciences, Department of
Organic Chemical Technology, Technical University of Budapest,
Budapest, Hungary
´
´
´
´
Gabor Blasko and Andras Dancso
EGIS Pharmaceuticals Ltd., Budapest, Hungary
´
´
´
´
´
Laszlo Toke and Miklos Nyerges
Research Group of the Hungarian Academy of Sciences, Department of
Organic Chemical Technology, Technical University of Budapest,
Budapest, Hungary
Abstract: The synthesis of some new functionalized quinolyl derivatives has
been described, based on the 1,3-dipolar cycloaddition of an azomethine
ylide, generated from sarcosine or N-benzylglycine and paraformaldehyde, to
2-chloro-3-quinolinecarbaldehydes.
Keywords: Dipolar cycloaddition, multicomponent reactions, oxazolines, quinolines
Quinolines and their derivatives are very important in medicinal chemistry
because of their wide occurrence in natural products[1] and drugs.[2]
Oxazole and its derivatives also have been incorporated into a large number
of compounds of potential medicinal value.[3]
The rapid and efficient generation of nitrogen-containing privileged
structural motifs is a great challenge in biological, organic, and medicinal
chemistry. Domino processes[4] and multicomponent reactions (MCRs)[5]
Received in Poland May 2, 2006
Address correspondence to Miklos Nyerges, Research Group of the Hungarian
´
Academy of Sciences, Department of Organic Chemical Technology, Technical Uni-
versity of Budapest, H-1521, Budapest, P.O.B. 91, Hungary. E-mail: mnyerges@
mail.bme.hu
3581

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J. Toth et al.
3582
offer excellent avenues to face these challenges. As a part of our research
program aimed at synthesizing nitrogen-containing druglike heterocyles by
the combined use of domino and multicomponent reactions, we became
interested in the oxazolidine-coupled quinoline molecules 3.
RESULTS AND DISCUSSION
The starting quinolines (2a–d) for the MCR were prepared by the method
described by O. Meth-Cohn from the corresponding acetanilides by the
treatment with the Vilsmeier reagent in a very effective domino reaction.[6]
Recently we have described the three-component reaction of aromatic
aldehydes, sarcosine, and paraformaldehyde, with a view to preparing
3-methyl-5-aryl-oxazolidines, which were valuable intermediates for
further elaboration to 2-dimethylamino-1-phenylethanols.[7] This process
utilizes a 1,3-dipolar cycloaddition reaction, which generally affords a
simple and convenient method for the regio- and stereoselective construction
of a variety of complex pyrrolidine derivatives. However, the azomethine
ylides can react with C55O double bonds in 1,3-dipolar cycloadditions, and
several oxazolidine-type cycloadducts have been described, but in these
cases either (a) the aldehyde component of the azomethine ylide, formed in
situ, was the same as the dipolarophile,[8] or (b) a stable precursor of the
azomethine ylide was prepared in advance and this was followed by the
cycloaddition step.[8a,9]
Based on these results, we synthesized with our MCR a variety of 5-(3-
quinolyl)-oxazilidine 3 by simple mixing of sarcosine or N-benzylglycine,
paraformaldehyde, and a 2-chloro-3-formyl-quinoline (as the dipolarophile)
in toluene and refluxing under Dean–Stark conditions (Scheme 1). In all
cases only the formaldehyde served as a component for the nonstabilized azo-
methine ylide generation, and the cycloadduct 3a–h was isolated in good
yield as the sole product (Table 1).
The heterocyclic ring structure of products 3a–e was confirmed by IR, 1H
NMR, and 13C NMR spectral studies. The 1H NMR and H-HCOSY spectra of
3c reveal two sharp singlets at d 2.53 and 3.92 due to the OCH3 of the
Scheme 1.

Synthesis of New Quinoline Derivatives
3583
Table 1. 1,3-Dipolar addition reaction of 2-chloro-3-formyl-quinolines (2a–e) and
azomethine ylide generated from paraformaldehyde and sarcosine
Entry
R1
R2
R3
Starting material
Product
Yield (%)
1
2
3
4
5
6
7
8
H
H
H
2a
2a
2b
2b
2c
2c
2d
2d
3a
3b
3c
3d
3e
3f
92
84
87
65
95
80
91
78
H
H
Ph
H
H
MeO
MeO
Me
Me
H
H
Ph
H
Cl
Cl
Me
Me
Ph
H
3g
3h
H
Ph
quinoline and N-methyl oxazolidine protons. Both of the N–CH2 proton of
H-4 appeared as a doublet of a doublet at d 3.62 and 2.85 (J ¼ 6.7 and
11.3 Hz). The H-5 proton exhibited as triplet at d 5.35 with J ¼ 6.5 Hz.
Two doublets appeared in the region d 4.66–4.53 (J ¼ 5.1 Hz) for H-2
protons.
The aromatic protons of the quinoline ring appeared as in the region of d
8.26–7.29 with the expected pattern. The 13C NMR spectra of 3c exhibited
peaks at d 89.3, 73.6, and 61.4 ppm for the oxazolidine ring carbons. The
peaks at d 55.5 ppm and at d 41.7 ppm are due to the oxazolidine N-methyl
and methoxy carbons of the quinoline ring respectively.
In conclusion, we have developed a new, two-step route by the combined
use of domino and multicomponent reactions from simple starting materials
for the synthesis of a 3-quinolyl-1,3-oxazolone ring system via the 1,3-
dipolar cycloaddition reaction of nonstabilized azomethine ylides to
aldehydes. This oxazolidines could be valuable building blocks of other
compunds of general interest.[10]
EXPERIMENTAL
General
Column chromatography was performed using Merck Kieselgel 60 70–230
mesh and thin-layer chromatography (TLC) on aluminium sheets coated
with Kieselgel 60 F254. Plates were stained with anisaldehyde solution
(100 ml glacial acetic acid, 2 ml of concn. sulphuric acid, and 1 ml of anisal-
dehyde) and heated at ca. 1508C. Phosphoryl chloride (Aldrich) and N,N-
dimethylformamide, anhydrous (Aldrich) were used as received. All
solvents were purified according to standard procedures. IR spectra were
obtained on a Bruker Vector 22 FT-IR instrument. NMR spectra were

´
J. Toth et al.
3584
obtained on Varian Inova 500 and Bruker DRX-500. Chemical shifts are given
relative to dTMS
.
General Procedure for the Synthesis of 2-Chloro-3-
quinolinecarbaldehydes (2a–d)
These compounds were prepared by the method of Meth-Cohn et al.[6]
N,N-Dimethylformamide (9.1 g, 9.6 ml, 0.125 mol) was cooled to 08C, and
phosphoryl chloride (53.7 g, 32.2 ml, 0.35 mol) was added dropwise with
stirring. To this solution was added the corresponding acetanilide
(0.05 mol), and the temperature of the reaction mixture was raised to 808C
for 18 h. The cooled reaction mixture was poured into ice water (300 ml)
and stirred for 1 h at 0–108C. The precipitated 2-chloro-3-quinolinecarbalde-
hyde was failtered off, washed with water (100 ml), dried, and recrystallized
from ethyl acetate to give the title product.
Data
2-Chloro-3-quinolinecarbaldehyde (2a): pale yellow powder (5.92 g, 62%),
1
mp 146–1478C (lit.[6b] 148–1498C); H NMR (500 MHz, CDCl3): 10.51
(s, 1H, CHO), 8.81 (s, 1H, H-4), 8.09 (d, 1H, J ¼ 8.2 Hz, H-5), 8.03 (d, 1H,
J ¼8.2 Hz, H-8), 7.92 (t, 1H, J ¼ 8.2 Hz, H-6), 7.69 (t, 1H, J ¼ 8.2 Hz,
H-7); HRMS (E.I) [M]þcalcd. for C10H6C1NO ¼ 191.01379; found
191.0147.
2-Chloro-6-methoxy-3-quinolinecarbaldehyde (2b): pale yellow powder
(5.41 g, 49%), mp 143–1448C (lit.[6b] 145.5–146.58C); 1H NMR
(500 MHz, CDCl3): 10.50 (s, 1H, CHO), 8.57 (s, 1H, H-4), 7.91 (d, 1H,
J ¼ 9.0 Hz, H-8); 7.46 (dd, 1H, J ¼ 9.0 Hz and 2.8 Hz, H-7), 7.17 (d, 1H,
J ¼ 2.8 Hz, H-5), 3.94 (s, 3H, OCH3); HRMS (E.I) [M]þcalcd. for
C11H8C1NO2 ¼ 221.02436; found 221.0261.
2,6-Dichloro-8-methyl-3-quinolinecarbaldehyde (2c): pale yellow powder
1
(4.68 g, 39%), mp 146–1488C; H NMR (500 MHz, CDCl3): 10.55 (s, 1H,
CHO), 8.61 (s, 1H, H-4), 7.78 (s, 1H, H-5), 7.67 (s, 1H, H-7), 2.77 (s, 3H,
Me); 13C NMR (125 MHz, CDCl3): 189.1 (q), 149.2 (q), 147.2 (q), 139.3
(CH), 139.2 (q), 134.1 (CH), 133.5 (q), 127.2 (q), 126.8 (q), 125.8 (CH),
17.7 (CH3); IR (KBr, cm21): 3050, 1693, 1628, 1582, 1379, 1038. HRMS
(E.I) [M]þcalcd. for C11H7C12NO ¼ 238.99047; found 238.9911.
2-Chloro-8-methyl-3-quinolinecarbaldehyde (2d): pale yellow powder
(7.40 g, 72%), mp 1388C (lit.[6b] 137–1388C); 1H NMR (500 MHz,
CDCl3): 10.52 (s, 1H, CHO), 8.64 (s, 1H, H-4), 7.76 (d, 1H, J ¼ 8.2 Hz,

Synthesis of New Quinoline Derivatives
3585
H-5), 7.68 (d, 1H, J ¼ 8.2 Hz, H-7), 7.50 (t, 1H, J ¼ 8.2 Hz, H-6), 2.75 (s, 3H,
CH3); HRMS (E.I) [M]þcalcd. for C11H8C1NO ¼ 205.02944; found
205.0301.
General Procedure for the Cycloaddition Reaction of Azomethine
Ylide Generated from Paraformaldehyde and Sarcosine
or N-Benzyl Glycine with 2-Chloro-3-formyl-quinolines (2a–d)
The corresponding 2-chloro-3-formyl-quinoline (1 mmol), sarcosine or
N-benzyl-glycine (2 mmol), and paraformaldehyde (5 mmol), were
suspended in toluene (50 ml), and the reaction mixture was then heated for
10 h under Dean–Stark conditions. After the reaction was complete, it was
filtered through a pad of Celite, the solvent was removed in vacuo, and the
residue was purified by flash chromatography (acetone/hexane 1:3).
Data
5-(2-Chloro-3-quinolyl)-3-methyl-1,3-oxazolone (3a): pale yellow oil. 1H
NMR (500 MHz, CDCl3): 8.40 (s, 1H, qui-H-4), 7.97 (d, 1H, J ¼ 8.2 Hz,
qui-H-5), 7.68 (d, 1H, J ¼ 8.2 Hz, qui-H-8), 7.55 (t, 1H, J ¼ 8.2 Hz, qui-
H-6), 7.50 (t, 1H, J ¼ 8.2 Hz, qui-H-7), 5.35 (t, 1H, J ¼ 6.9 Hz, H-5), 4.65
(d, 1H, J ¼ 5.0 Hz, H-2), 4.52 (d, 1H, J ¼ 5.0 Hz, H-2), 3.61 (dd, 1H,
J ¼ 6.9 and 11.1 Hz, H-4), 2.85 (dd, 1H, J ¼ 6.9 and 11.1 Hz, H-4), 2.51
(s, 3H, NCH3); 13C NMR (125 MHz, CDCl3): 148.0 (q), 146.6 (q), 146.65
(q), 134.4 (CH), 129.9 (CH), 127.9 (CH), 127.4 (CH), 127.1 (q), 126.9 (CH),
89.2 (CH2), 73.4 (CH), 61.2 (CH2), 41.4 (CH3); IR (neat, cm21): 3061, 2951,
2870, 2800, 1676, 1619, 1592, 1565, 1492, 1455, 1398, 1326, 1158, 1055,
1029; HRMS (E.I) [M]þcalcd. for C13H13C1 N2O ¼ 248.07164; found
248.0739.
1
5-(2-Chloro-3-quinolyl)-3-benzyl-1,3-oxazolone (3b): pale yellow oil. H
NMR (500 MHz, CDCl3): 8.36 (s, 1H, qui-H-4), 7.99 (d, 1H, J ¼ 7.8 Hz,
qui-H-5), 7.81 (d, 1H, J ¼ 7.8 Hz, qui-H-8), 7.67 (t, 1H, J ¼ 7.8 Hz, qui-H-
6), 7.52 (t, 1H, J ¼ 7.8 Hz, qui-H-7), 7.34–7.24 (m, 5H, Ph), 5.35 (t, 1H,
J ¼ 7.0 Hz, H-5), 4.67 (d, 1H, J ¼ 5.5 Hz, H-2), 4.63 (d, 1H, J ¼ 5.5 Hz,
H-2), 3.81 (s, 2H, NCH2), 3.74 (dd, 1H, J ¼ 7.0 and 11.7 Hz, H-4), 2.86
(dd, 1H, J ¼ 7.0 and 11.7 Hz, H-4); 13C NMR (125 MHz, CDCl3): 148.1
(q), 146.7 (q), 138.2 (q), 134.4 (q), 134.3 (q), 129.9 (CH), 128.5 (2 ꢀ CH),
128.3 (2 ꢀ CH), 128.0 (CH), 127.5 (CH), 127.3 (CH), 127.2 (CH),
127.0 (CH), 87.2 (CH2), 73.4 (CH), 59.2 (CH2), 58.3 (CH2). IR (neat,
cm21): 3062, 2927, 2876, 1676, 1592, 1565, 1493, 1454, 1398, 1326, 1076,
927; HRMS (E.I) [M]þcalcd. for C19H17C1 N2O ¼ 324.10294; found
324.1001.

´
J. Toth et al.
3586
5-(6-Methoxy-2-chloro-3-quinolyl)-3-methyl-1,3-oxazolone (3c): pale
1
yellow oil. H NMR (500 MHz, CDCl3): 8.26 (s, 1H, qui-H-4), 7.89 (d, 1H,
J ¼ 9.2 Hz, qui-H-8), 7.35 (dd, 1H, J ¼ 2.8 and 9.2 Hz, qui-H-7), 7.09
(d, 1H, J ¼ 2.8 Hz, qui-H-5), 5.35 (t, 1H, J ¼ 6.5 Hz, H-5), 4.66 (d, 1H,
J ¼ 5.1 Hz, H-2), 4.53 (d, 1H, J ¼ 5.1 Hz, H-2), 3.92 (s, 3H, OCH3), 3.62
(dd, 1H, J ¼ 6.7 and 11.3 Hz, H-4), 2.85 (dd, 1H, J ¼ 6.7 and 11.3 Hz,
H-4), 2.53 (s, 3H, NCH3); 13C NMR (125 MHz, CDCl3): 158.2 (CH), 145.5
(q), 142.8 (q), 134.7 (CH), 133.3 (q), 129.5 (CH), 128.4 (q), 122.7 (CH),
105.2 (CH), 89.3 (CH2), 73.6 (CH), 61.4 (CH2), 55.5 (CH3), 41.7 (CH3);
IR (neat, cm21): 2955, 2870, 2801, 1671, 1623, 1592, 1498, 1455,
1329, 1228, 1165, 1123, 1056, 1032, 959; HRMS (E.I) [M]þcalcd. for
C14H15C1 N2O2 ¼ 278.08220; found 278.0852.
5-(6-Methoxy-2-chloro-3-quinolyl)-3-benzyl-1,3-oxazolone (3d): pale yellow
oil. 1H NMR (500 MHz, CDCl3): 8.25 (s, 1H, qui-H-4), 7.86 (d, 1H, J ¼ 9.2 Hz,
qui-H-8), 7.33–7.25 (m, 6H, Ph and qui-H-7), 7.06 (d, 1H, J ¼ 2.8 Hz, qui-H-
5), 5.33 (t, 1H, J ¼ 6.8 Hz, H-5), 4.66 (d, 1H, J ¼ 5.5 Hz, H-2), 3.87 (s, 3H,
OCH3), 3.81 (s, 2H, NCH2), 3.72 (dd, 1H, J ¼ 6.8 and 11.8 Hz, H-4), 3.57
(dd, 1H, J ¼ 6.8 and 11.8 Hz, H-4); 13C NMR (125 MHz, CDCl3): 158.0 (q),
145.4 (q), 142.6 (q), 138.2 (q), 134.5 (q), 133.1 (CH), 129.3 (CH), 128.5
(2 ꢀ CH), 128.3 (2 ꢀ CH), 128.2 (q), 127.2 (CH), 122.5 (CH), 105.0 (CH),
87.1 (CH2), 73.3 (CH), 59.2 (CH2), 58.2 (CH2), 55.3 (CH3). IR (neat, cm21):
3062, 2935, 2878, 1674, 1594, 1498, 1454, 1329, 1061, 998; HRMS (E.I)
[M]þcalcd. for C20H19C1 N2O2 ¼ 354.11350; found 354.1147.
5-(2,8-Dichloro-6-methyl-3-quinolyl)-3-methyl-1,3-oxazolone (3e): pale
1
yellow oil. H NMR (500 MHz, CDCl3): 8.23 (s, 1H, qui-H-4), 7.65 (d, 1H,
J ¼ 2.1 Hz, qui-H-5), 7.49 (d, 1H, J ¼ 2.1 Hz, qui-H-7), 5.35 (t, 1H,
J ¼ 6.5 Hz, H-5), 4.65 (d, 1H, J ¼ 5.1 Hz, H-2), 4.53 (d, 1H, J ¼ 5.1 Hz,
H-2), 3.56 (dd, 1H, J ¼ 6.5 and 11.5 Hz, H-4), 2.84 (dd, 1H, J ¼ 6.5 and
11.5 Hz, H-4), 2.73 (s, 3H, CH3), 2.52 (s, 3H, CH3); 13C NMR (125 MHz,
CDCl3): 147.4 (q), 144.6 (q), 138.6 (q), 135.5 (q), 133.8 (CH), 132.4 (q),
130.8 (CH), 128.0 (q), 124.0 (CH), 89.4 (CH2), 73.5 (CH), 61.3 (CH2), 41.6
(CH3), 17.6 (CH3); IR (KBR, cm21): 3694, 2963, 2794, 1654, 1522, 1322,
1263, 1099, 1022; HRMS (E.I) [M]þcalcd. for C14H14C12N2O ¼ 296.04831;
found 296.0499.
5-(2,8-Dichloro-6-methyl-3-quinolyl)-3-benzyl-1,3-oxazolone (3f): pale
1
yellow oil. H NMR (500 MHz, CDCl3): 8.24 (s, 1H, qui-H-4), 7.65 (s, 1H,
qui-H-5), 7.49 (s, 1H, qui-H-7), 7.36–7.25 (m, 5H, Ph), 5.35 (t, 1H,
J ¼ 7.0 Hz, H-5), 4.67 (d, 1H, J ¼ 5.6 Hz, H-2), 4.63 (d, 1H, J ¼ 5.6 Hz,
H-2), 3.83 (s, 2H, NCH2), 3.76 (dd, 1H, J ¼ 7.0 and 11.8 Hz, H-4), 3.73
(dd, 1H, J ¼ 7.0 and 11.8 Hz, H-4), 2.72 (s, 3H, CH3); 13C NMR
(125 MHz, CDCl3): 147.4 (q), 144.6 (q), 138.6 (q), 138.3 (q), 135.4 (q),
133.8 (CH), 132.4 (q), 130.8 (CH), 128.7 (2 ꢀ CH), 128.5 (2 ꢀ CH), 127.9

Synthesis of New Quinoline Derivatives
3587
(q), 127.4 (CH), 124.1 (CH), 87.4 (CH2), 73.4 (CH), 59.3 (CH2), 58.4 (CH2),
17.6 (CH3); IR (neat, cm21): 3063, 2925, 2876, 1701, 1592, 1479, 1454, 1327,
1053, 997; HRMS (E.I) [M]þcalcd. for C20H18C12N2O ¼ 372.07961; found
372.0811.
5-(8-Methyl-2-chloro-3-quinolyl)-3-methyl-1,3-oxazolone (3g): pale yellow
oil. 1H NMR (500 MHz, CDCl3): 8.31 (s, 1H, qui-H-4), 7.65 (d, 1H,
J ¼ 8.1 Hz, qui-H-5), 7.52 (d, 1H, J ¼ 8.1 Hz, qui-H-7), 7.42 (t, 1H, J ¼
8.1 Hz, qui-H-6), 5.36 (t, 1H, J ¼ 6.7 Hz, H-5), 4.65 (d, 1H, J ¼ 5.0 Hz,
H-2), 4.53 (d, 1H, J ¼ 5.1 Hz, H-2), 3.63 (dd, 1H, J ¼ 6.7 and 11.5 Hz,
H-4), 2.85 (dd, 1H, J ¼ 6.7 and 11.5 Hz, H-4), 2.75 (s, 3H, CH3), 2.53
(s, 3H, NCH3); 13C NMR (125 MHz, CDCl3): 147.1 (q), 146.1 (q), 136.2
(CH), 134.6 (q), 134.1 (q), 130.0 (CH), 127.3 (CH), 126.7 (q), 125.5 (CH),
89.3 (CH2), 73.5 (CH), 61.4 (CH2), 41.6 (CH3), 17.7 (CH3); IR (neat,
cm21): 3010, 2952, 2860, 2806, 1653, 1599, 1576, 1485,1463, 1395, 1377,
1363, 1323, 1206, 1170, 1122, 1088, 1060, 1044, 1009; HRMS (E.I)
[M]þcalcd. for C14H15C1 N2O ¼ 262.08729; found 262.0879.
5-(8-Methyl-2-chloro-3-quinolyl)-3-benzyl-1,3-oxazolone (3h): pale yellow
oil. 1H NMR (500 MHz, CDCl3): 8.32 (s, 1H, qui-H-4), 7.66 (d, 1H,
J ¼ 7.2 Hz, qui-H-5), 7.51 (d, 1H, J ¼ 7.2 Hz, qui-H-7), 7.42 (t, 1H,
J ¼ 7.2 Hz, qui-H-6), 7.34–7.22 (m, 5H, Ph), 5.36 (t, 1H, J ¼ 6.7 Hz, H-5),
4.67 (d, 1H, J ¼ 5.5 Hz, H-2), 4.63 (d, 1H, J ¼ 5.5 Hz, H-2), 3.82 (s, 2H,
NCH2), 3.74 (dd, 1H, J ¼ 7.2 and 11.8 Hz, H-4), 2.86 (dd, 1H, J ¼ 7.2 and
11.8 Hz, H-4), 2.74 (s, 3H, CH3); 13C NMR (125 MHz, CDCl3): 147.1 (q),
146.1 (q), 138.3 (q), 136.3 (q), 134.6 (CH), 134.1 (q), 130.1 (CH), 128.6
(2 ꢀ CH), 128.4 (2 ꢀ CH), 128.4 (q), 127.3 (CH), 126.8 (CH), 125.5 (CH),
87.3 (CH2), 73.5 (CH), 59.4 (CH2), 58.4 (CH2), 19.0 (CH3); IR (neat,
cm21): 3062, 2876, 1641, 1597, 1495, 1454, 1326, 1075, 905; HRMS (E.I)
[M]þcalcd. for C20H19C1 N2O ¼ 338.11859; found 338.1197.
ACKNOWLEDGMENTS
This work was financially supported by the National Fund for Science and
Research, Hungary (OTKA Project No. T 046196). N. M. thanks the
Hungarian Academy of Sciences for a Bolyai J. Fellowship. A grant from
´
the Jozsef Varga Foundation provided to J. T. is gratefully appreciated.
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