Facile access to bicyclic sultams with methyl 1-sulfonylcyclopropane-l- carboxylate moieties

Article abstract of DOI:10.1002/ejoc.200900113

N-(2,3-Dibromopropyl)- and N-(3,4-dibromobutyl)(methoxycarbonyl) methanesulfanilides upon treatment with potassium carbonate in DMF furnish, methyl 3-aryl-2,2-dioxo-2thia-3-azabicyclo[n.1.0]alkane-1.-carboxylates in yields ranging from 54 to 84% (10 examples). The starting materials were obtained by sulfonylation of N-alkenylanilines with methyl (chlorosulfonyl) acetate and. subsequent bromination. For the N-alkenylanil.in.es (10 examples, 60-77% yield) an efficient new synthesis employing a 2-nitrophenylsulfonyl substituent as a protective as well as an activating group has been developed. The 4-methoxyphenyl (PMP) group could easily be removed, from, the sultam. nitrogen atom by treatment with cerium(IV) ammonium nitrate.

Full text of DOI:10.1002/ejoc.200900113

FULL PAPER
DOI: 10.1002/ejoc.200900113
Facile Access to Bicyclic Sultams with Methyl
1-Sulfonylcyclopropane-1-carboxylate Moieties[‡]
Valentin A. Rassadin,[a] Aleksandr A. Tomashevskiy,[a] Viktor V. Sokolov,*[a] Arne Ringe,[b]
Jörg Magull,[b] and Armin de Meijere*[c]
Keywords: N-Alkenylanilines / Intramolecular cyclodialkylation / Cyclopropanes / Oxidative deprotection
N-(2,3-Dibromopropyl)- and N-(3,4-dibromobutyl)(meth-
oxycarbonyl)methanesulfanilides upon treatment with potas-
sium carbonate in DMF furnish methyl 3-aryl-2,2-dioxo-2-
thia-3-azabicyclo[n.1.0]alkane-1-carboxylates in yields rang-
ing from 54 to 84% (10 examples). The starting materials
were obtained by sulfonylation of N-alkenylanilines with
methyl (chlorosulfonyl)acetate and subsequent bromination.
For the N-alkenylanilines (10 examples, 60–77% yield) an
efficient new synthesis employing a 2-nitrophenylsulfonyl
substituent as a protective as well as an activating group has
been developed. The 4-methoxyphenyl (PMP) group could
easily be removed from the sultam nitrogen atom by treat-
ment with cerium(IV) ammonium nitrate.
(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim,
Germany, 2009)
cyclodialkylations occurring in N-(ω-1,ω-dibromoalkyl)-
(methoxycarbonyl)methanesulfanilides 1 (Scheme 1).
Introduction
Earlier on, our group has reported intermolecular reac-
tions between sulfonamides, obtained from different ani-
lines and alkyl 2-(chlorosulfonyl)acetates, with a wide range
of alkylating agents.[1] As it turned out, cyclodialkylation of
such sulfonamides with 1,ω-dibromides constitutes an ef-
ficient route to five-, six- and seven-membered sultams with
an α-methoxycarbonyl group. Here we report the results of
our investigation concerning analogous intramolecular
Results and Discussion
The acyclic N-(ω-1,ω-dibromoalkyl)(methoxycarbonyl)-
methanesulfanilides of type 1 were prepared from the corre-
sponding N-(ω-alkenyl)(methoxycarbonyl)methanesulfanil-
ides, which were obtained from the corresponding N-alken-
ylanilines. Initially, the parent N-allylaniline (5a) was pre-
pared by allylation of formanilide (3) and subsequent de-
formylation in 78% overall yield (Scheme 2). A more conve-
nient general access to N-(ω-alkenyl)anilines, avoiding the
use of sodium hydride, was developed starting from 2-nitro-
benzenesulfanilides 7 obtained from the sulfonyl chloride 6
and the respective aniline. Alkylation of compounds 7 with
allyl, homoallyl and 4-pentenyl bromides afforded the N-(2-
nitrophenylsulfonyl)anilines 8, 9 and 11, respectively, from
which the protective and at the same time activating 2-ni-
trophenylsulfonyl group could cleanly be removed by treat-
ment with thiophenol/potassium carbonate in DMF. The
yields over all three steps in this sequence ranged from 61
to 77% (Scheme 2, Table 1).
Scheme 1. Concept for the intramolecular cyclodialkylation of
methoxycarbonylmethanesulfanilides.
[‡] For Armin de Meijere: Cyclopropyl Building Blocks for Or-
ganic Synthesis, 152. Part 151: M. W. Nötzel, D. Frank, T. Lab-
ahn, A. de Meijere, Eur. J. Org. Chem. 2009, 1683–1686. Part
150: M. Limbach, A. Lygin, M. Es-Sayed, A. de Meijere, Eur.
J. Org. Chem. 2009, 1357–1364.
[a] Department of Chemistry, Saint-Petersburg State University,
Universitetskii pr. 26, 198504 Saint-Petersburg, Russia
E-mail: vsokolo@mail.ru
N-Alkenylanilines 5, 10 and 12 reacted smoothly with
methyl (chlorosulfonyl)acetate[2] to give the corresponding
sulfonamides 13–15 in good yields (Scheme 3 and Table 2).
Addition of bromine to the C=C double bonds in sulf-
amides 13–15 occurred quantitatively to give the correspond-
ing dibromoalkyl derivatives 16, 18, 20 in virtually pure
[b] Institut für Anorganische Chemie der Georg-August-Uni-
versität,
Tammannstrasse 4, 37077 Göttingen, Germany
E-mail: aringe1@gwdg.de
[c] Institut für Organische und Biomolekulare Chemie der Georg-
August-Universität,
1
Tammannstrasse 2, 37077 Göttingen, Germany
E-mail: ameijer1@gwdg.de
form according to their H NMR spectra. Upon treatment
with potassium carbonate in DMF, the (dibromoalkyl)sul-
fonamides 16 and 18 underwent intramolecular cyclodialky-
Supporting information for this article is available on the
WWW under http://www.eurjoc.org or from the author.
Eur. J. Org. Chem. 2009, 2635–2641
© 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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V. V. Sokolov, A. de Meijere et al.
FULL PAPER
Table 2. Transformation of N-alkenylanilines to bicyclic sultams
(see Scheme 3).
Ar
Product
% Yield
Product
% Yield
Ph
13a
13b
13c
13d
13e
14a
14b
14c
14d
14e
15a
74
73
81
76
74
65
70
60
78
74
70
17a
17b
17c
17d
17e
19a
19b
19c
19d
19e
21a
80
83
76
68
73
63
54
84
60
58
4-MeC6H4
2,6-Me2C6H3
4-ClC6H4
4-MeOC6H4
Ph
4-MeC6H4
2,6-Me2C6H3
4-ClC6H4
4-MeOC6H4
Ph
[a]
–
[a] Complex mixture of products.
lation of their C,H-acidic positions to yield the bicyclic sul-
tams 17, 19. While the reactions of dibromides 16 leading to
the cyclopropane-annelated five-membered sultams 17 were
complete within 2 h, without any noticeable influence of the
aryl substituents on the yield and reaction time, the homol-
ogous starting materials 18 required longer reaction times
(12 h) and furnished the cyclopropane-annelated six-mem-
bered sultams 19 mostly in lower yields. It is noteworthy,
that for the 2,6-dimethylaniline derivatives 17c and 19c, an-
alogues of which were found to be most reactive in the
intermolecular cyclodialkylations,[1] the reaction times were
the shortest. Under the established conditions, the dibro-
moalkyl derivative 20a obtained by bromine addition to the
N-pentenylaniline derivative 15a gave a complex mixture
from which the expected 2-thia-3-azabicyclo[5.1.0]octane
derivative 21a could not be isolated.
The structure of the sultam 17a was proved by X-ray
crystallography (see Figure 1). In the crystal, the 2-thia-3-
azabicyclo[3.1.0]hexane skeleton adopts a flattened boat
conformation, as is frequently observed for bicyclo[3.1.0]-
hexane derivatives.[4] The interplanar angle between the
three- and five-membered rings is 110.4°, and the nitrogen
corner of the five-membered ring is bent by an angle of
34.3° towards the three-membered ring. The C=C bond dis-
tal to the two electron-withdrawing groups is shorter
[147.5(2) pm] than the two proximal bonds [152.0(2) and
152.6(2) pm], a typical effect caused by electron-with-
drawing substituents on a cyclopropane ring.[5] The coordi-
nation around the nitrogen is virtually trigonally planar.
Scheme 2. Preparation of various N-alkenylanilines. For further de-
tails see Table 1. (a) NaH, THF, reflux, 4 h; (b) allylBr, THF, reflux,
3 h; (c) aq. HCl, 60 °C, 1 h; (d) ArNH2, AcONa, 50% aq. EtOH;
(e) CH2=CH(CH2)nBr, K2CO3, DMF; 7 Ǟ 8: room temp., 2 h;
7 Ǟ 9, 11: 40 °C, 12 h; (f) PhSH, K2CO3, DMF, 40 °C, 3 h.
Table 1. Preparation of various N-alkenylanilines (see Scheme 2).
Ar
Product
% Yield[a]
4-MeC6H4
2,6-Me2C6H3
4-ClC6H4
4-MeOC6H4
Ph
4-MeC6H4
2,6-Me2C6H3
4-ClC6H4
4-MeOC6H4
Ph
5b
5c
75
76
75
77
60
65
70
61
61
61
5d
5e
10a
10b
10c
10d
10e
12a
[a] Over 3 steps.
Scheme 3. Transformation of N-alkenylanilines to bicyclic sultams.
For further details see Table 2. (a) ClSO2CH2CO2Me, Py, MeCN,
10 °C; (b) Br2, CH2Cl2, 0 °C, 30 min; (c) K2CO3, DMF, 50 °C, 4 h
(15 h for sultams 19).
Figure 1. Structure of methyl 2,2-dioxo-3-phenyl-2-thia-3-azabicy-
clo[3.1.0]hexane-1-carboxylate (17a) in the crystal.[3]
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Bicyclic Sultams with Cyclopropane Moieties
Scheme 4. Oxidative removal of the PMP group from several sultams under various conditions.
The bisacceptor-substituted cyclopropane ring in the bi- leads to bicyclic sultams containing 1-methoxycarbonyl-1-
cyclic sultams 17 turned out to be rather resistant towards sulfamoylcyclopropane moieties annelated to five- and six-
attack by common nucleophiles.[6] Thus, the compound 17a membered rings. These compounds essentially are confor-
was recovered unchanged after treatment with thiophenol/ mationally rigidified γ-aminobutyric and δ-aminovaleric
potassium carbonate in DMF at 50 °C for 2 d.
acid derivatives which ought to be useful for incorporation
In an attempt to prepare sultams of type 17 without an in small peptide mimetics after oxidative removal of the N-
aryl group on nitrogen, the N-(4-methoxyphenyl) derivative (4-methoxyphenyl) group and cleavage of the ester moiety.
17e was treated with RuO4 generated in situ from RuCl3
and two different co-oxidants.[7] However, treatment of sul-
tam 17e with RuCl3 and NaIO4 gave the sulfamoyl-substi-
Experimental Section
tuted monomethyl cyclopropane-1,2-dicarboxylate 22 as
General Remarks: All reagents were used as purchased without fur-
the main product and the N-dearylated sultam 23 in inac-
ther purification. The solvents were purified and dried prior to use
ceptable low yield (10%). After a systematic optimization
according to conventional methods. 1H and 13C NMR spectra were
of the reaction conditions, with changes of the quantity of
recorded at ambient temperature with a Bruker AM 250 instrument
co-oxidant and the rate of its addition to the reaction mix-
at 250.13 (1H) and 62.90 (13C and DEPT) MHz and Bruker DPX
ture, the sultam 23 was eventually obtained in 30% yield
(Scheme 4). Treatment of sultam 17e with RuCl3 and per-
iodic acid instead of sodium periodate as the co-oxidant,
furnished compound 22 as the single product in excellent
yield (92%).
The removal of N-(4-methoxyphenyl) groups from car-
boxamides has previously been achieved with cerium(IV)
ammonium nitrate (CAN) under mild conditions,[8] but to
the best of our knowledge, there have been no reports con-
cerning the analogous cleavage of N-(4-methoxyphenyl)sul-
fonamides. Yet, the same conditions as applied for N-(4-
methoxyphenyl)-substituted carboxamides can be used to
remove the PMP group from the bicyclic 17e, 19e as well as
the monocyclic sultams 25, 27[1] with good to excellent
300 instrument at 300.13 (1H) and 75.54 (13C and DEPT) MHz.
Chemical shifts (δ) are given in ppm relative to resonances of sol-
vents (1H: δ = 7.26 for CHCl3 and δ = 2.50 ppm for [D5]DMSO;
13C: δ = 77.0 for CDCl3 and δ = 39.7 ppm for [D6]DMSO). Coup-
ling constants (J) are given in Hz. Multiplicities of signals are de-
scribed as follows: s = singlet, d = doublet, t = triplet, q = quadru-
plet, m = multiplet. The multiplicities of signals in 13C NMR spec-
tra were determined by the DEPT technique. Mass spectra were
recorded with a Finnigan MAT 95 spectrometer. Chromatographic
separation was carried out on Merck silica gel 60 (0.063–
0.200 mm). Analytical TLC was performed on Macherey–Nagel
ready-to-use plates AluGram® Sil G/UV254
achieved by development with molybdatophosphoric acid solution
(5% in ethanol). Melting points (uncorrected) were determined in
capillaries with a Büchi 510 apparatus. Elemental analyses of solid
. Detection was
yields (68–89%) of the products 23, 24, 26 and 28, respec- compounds: Mikroanalytisches Laboratorium des Instituts für Or-
ganische und Biomolekulare Chemie der Georg-August-Uni-
versität, Göttingen.
tively.
N-Allylaniline (5a):
0.95 mol) in THF (200 mL) was added slowly to a stirred suspen-
sion of NaH (60% dispersion in oil, 40.0 g, 1.00 mol) in anhydrous
A solution of formanilide (3) (113.5 g,
Conclusions
Cyclizing intramolecular dialkylation of N-(ω-1,ω-di-
bromoalkyl)(methoxycarbonyl)methanesulfanilides readily THF (300 mL), and the reaction mixture was heated at reflux for
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V. V. Sokolov, A. de Meijere et al.
FULL PAPER
4 h. Then allyl bromide (121.0 g, 1.00 mol) was added, and the mix-
ture was heated at reflux for an additional 3 h, cooled to room
temp. and diluted with water (200 mL). The organic layer was sepa-
rated, washed with brine (2ϫ75 mL), dried with Na2SO4 and the
solvents evaporated in vacuo. A mixture of residual crude N-allyl-
formanilide (4) thus obtained and 10% HCl (335 mL) was stirred at
70 °C for 1 h, cooled to 0 °C and made strongly alkaline by careful
addition of solid NaOH. The mixture was extracted with Et2O
(3ϫ80 mL), the combined organic layers washed with brine, dried
with Na2SO4 and concentrated, the residue was distilled in vacuo
to afford N-allylaniline (5a) 99.1 g (92%) as a colorless oil; b.p. 65–
70 °C (2 Torr); lit.[9] b.p. 115 °C (23 Torr).
N-(But-3-enyl)-N-phenyl-2-nitrobenzenesulfonamide (9a): Yield
13.1 g (79%), slightly yellow solid, m.p. 74–76 °C. 1H NMR
(250 MHz, CDCl3): δ = 2.23 (q, J = 7.2 Hz, 2 H, NCH2CH2), 3.87
(t, J = 7.2 Hz, 2 H, NCH2), 5.02–5.10 (m, 2 H, CH=CH2), 5.69–
5.85 (m, 1 H, CH=CH2), 7.19–7.23 (m, 3 H, ArH), 7.32–7.34 (m,
2 H, ArH), 7.44–7.47 (m, 2 H, ArH), 7.60–7.64 (m, 2 H, ArH)
ppm. 13C NMR (63 MHz, CDCl3): δ = 33.1 (NCH2CH2), 51.6
(NCH2), 117.5 (CH=CH2), 123.8 (CH=CH2), 128.6 (CH-Ar), 129.5
(2 C, CH-Ar), 129.7 (2 C, CH-Ar), 131.1 (CH-Ar), 131.8 (CH-Ar),
132.0 (C-Ar), 133.7 (CH-Ar), 134.4 (CH-Ar), 137.7 (C-Ar), 148.1
(C-Ar) ppm. MS (EI, 70 eV): m/z (%) = 332 (2) [M+], 291 (62), 186
(100), 105 (44), 77 (24). C16H16N2O4S (332.4): calcd. C 57.82, H
4.85, N 8.43; found C 57.63, H 4.70, N 8.29.
General Procedure for the Synthesis of N-Aryl-2-nitrobenzenesulfon-
amides 7a–e (GP1): 2-nitrobenzenesulfonyl chloride (6) (33.2 g,
150 mmol) was added in small portions to a vigorously stirred mix-
ture of the respective aniline (180 mmol) and NaOAc (17.2 g,
210 mmol) in 50% aq. MeOH (150 mL) over a period of 30 min.
The mixture was then stirred at 60 °C for 1 h, cooled to room
temp., diluted with water (600 mL) and acidified to pH 2 with
concd. HCl. The precipitate was filtered off, washed thoroughly
with water and recrystallized from EtOAc/hexane to afford the cor-
responding 2-nitrobenzenesulfonanilide. According to GP1 the fol-
lowing sulfonamides were prepared:
N-(But-3-enyl)-N-(4-methylphenyl)-2-nitrobenzenesulfonamide (9b):
Yield 14.2 g (82%), slightly yellow solid, m.p. 96–97 °C. H NMR
1
(250 MHz, CDCl3): δ = 2.23 (q, J = 7.1 Hz, 2 H, NCH2CH2), 2.34
(s, 3 H, CH3), 4.36 (t, J = 7.1 Hz, 2 H, NCH2), 5.02–5.09 (m, 2 H,
CH=CH2), 5.69–5.85 (m, 1 H, CH=CH2), 7.05–7.14 (m, 4 H,
ArH), 7.42–7.51 (m, 2 H, ArH), 7.58–7.67 (m, 2 H, ArH) ppm. 13
C
NMR (63 MHz, CDCl3): δ = 21.2 (CH3), 33.1 (NCH2CH2), 51.6
(NCH2), 117.4 (CH=CH2), 123.8 (CH=CH2), 129.5 (2 C, CH-Ar),
130.1 (2 C, CH-Ar), 131.1 (CH-Ar), 132.0 (CH-Ar), 132.1 (C-Ar),
133.6 (CH-Ar), 134.5 (CH-Ar), 135.0 (C-Ar), 138.7 (C-Ar), 148.1
(C-Ar) ppm. MS (EI, 70 eV): m/z (%) = 346 (6) [M+], 305 (65), 186
(27), 119 (100), 91 (24). C17H18N2O4S (346.4): calcd. C 58.94, H
5.24, N 8.09; found C 58.73, H 5.04, N 8.09.
2-Nitro-N-phenylbenzenesulfonamide (7a): Yield 41.3 g (99%), col-
orless solid, m.p. 117–119 °C; lit.[10] m.p. 118–120 °C.
N-(4-Methylphenyl)-2-nitrobenzenesulfonamide (7b): Yield 41.6 g
(95%), slightly yellow solid, m.p. 117–118 °C; lit.[11] m.p. 114–
116 °C.
General Procedure for the Synthesis N-Alkenylanilines 5, 10, 12
(GP3): A mixture of the respective N-alkenyl-N-aryl-2-nitroben-
zenesulfonamide (44.0 mmol), thiopenol (11.0 g, 100.0 mmol) and
anhydrous K2CO3 (19.3 g, 140.0 mmol) in DMF (50 mL) was
stirred at 40 °C for 4 h. The mixture was poured into water
(350 mL) and extracted with Et2O (3ϫ100 mL). The ethereal
phase was washed with water (5ϫ100 mL), then treated with 3 
HCl (3ϫ100 mL) to extract the amine hydrochloride into the aque-
ous phase. The latter was washed with Et2O (2ϫ50 mL), then
made strongly alkaline by carefull addition of solid NaOH. The
mixture was extracted with Et2O (3ϫ70 mL), the combined ex-
tracts were washed with water (100 mL), brine (50 mL) and dried
with MgSO4. The solvent was removed in vacuo on a rotary evapo-
rator, the crude product distilled in vacuo (in some cases the crude
amine was used in the next step without purification) to afford the
corresponding N-alkenylaniline. According to GP3 the following
amines were prepared.
N-(2,6-Dimethylphenyl)-2-nitrobenzenesulfonamide
(7c):
Yield
42.7 g (93%), colorless solid, m.p. 163–165 °C; lit.[11] m.p. 163–
164 °C.
N-(4-Chlorophenyl)-2-nitrobenzenesulfonamide (7d): Yield 45.4 g
(97%), slightly green solid, m.p. 124–125 °C; lit.[12] m.p. 123–
124 °C.
N-(4-Methoxyphenyl)-2-nitrobenzenesulfonamide (7e): Yield 41.6 g
(90%), gray solid, m.p. 106–107 °C; lit.[12] m.p. 106–108 °C.
General Procedure for the Preparation of N-Alkenyl-N-aryl-2-nitro-
benzenesulfonamides 8, 9, 11 (GP2): A mixture of the respective
N-aryl-2-nitrobenzenesulfonamide (7) (50.0 mmol), the respective
alkenyl bromide (55.0 mmol) and anhydrous K2CO3 (10.4 g,
75.0 mmol) in DMF (50 mL) was stirred at the given temperature
for the stated time (see Scheme 2). The mixture was poured into
water (350 mL) and extracted with CH2Cl2 (3ϫ75 mL). The com-
bined organic phases were washed with water (5ϫ100 mL), dried
with MgSO4 and concentrated in vacuo. The solid residue was puri-
fied by recrystallization from EtOAc/hexane to afford the corre-
sponding sulfonamide. According to GP2 the following sulfon-
amides were prepared:
N-Allyl-4-methylaniline (5b):[12] Yield 5.88 g (91%), colorless oil,
b.p. 105–109 °C (2 Torr).
N-Allyl-2,6-dimethylaniline (5c):[13] Yield 6.60 g (87%), colorless
oil.
N-Allyl-4-chloroaniline (5d):[14] Yield 6.53 g (84%), colorless oil,
b.p. 110–114 °C (2 Torr).
N-Allyl-4-methoxyaniline (5e):[14] Yield 7.01 g (90%), reddish oil.
N-(But-3-enyl)aniline (10a):[15] Yield 5.29 g (85%), colorless oil.
N-(But-3-enyl)-4-methylaniline (10b):[16] Yield 5.47 g (83%), color-
N-Allyl-N-(4-methylphenyl)-2-nitrobenzenesulfonamide (8b): Yield
14.4 g (87%), slightly yellow solid, m.p. 124–125 °C. 1H NMR
(300 MHz, CDCl3): δ = 2.32 (s, 3 H, CH3), 4.36 (dt, J = 1.2, 6.5 Hz,
2 H, NCH2), 5.06–5.14 (m, 2 H, CH=CH2), 5.81 (ddt, J = 6.4,
10.3, 16.7 Hz, 1 H, CH=CH2), 7.02–7.12 (m, 4 H, ArH), 7.44–7.69
less oil.
(m, 4 H, ArH) ppm. 13C NMR (75 MHz, CDCl3): δ = 21.2 (CH3), N-(But-3-enyl)-2,6-dimethylaniline (10c): Yield 6.62 g (90%), color-
55.2 (NCH2), 119.1 (CH=CH2), 123.9 (CH=CH2), 129.5 (2 C, CH- less oil. 1H NMR (250 MHz, CDCl3): δ = 2.28 (s, 6 H, 2 CH3),
Ar), 130.0 (2 C, CH-Ar), 131.2 (CH-Ar), 132.1 (CH-Ar), 132.3 (C-
2.31–2.40 (m, 2 H, NCH2CH2), 3.07 (dt, J = 0.7, 6.7 Hz, 3 H,
Ar), 133.1 (CH-Ar), 133.7 (CH-Ar), 135.1 (C-Ar), 138.6 (C-Ar), HNCH2), 5.11–5.22 (m, 2 H, CH=CH2), 5.77–5.94 (m, 1 H,
148.1 (C-Ar) ppm. MS (EI, 70 eV): m/z (%) = 332 (3) [M+], 146
(100), 130 (23), 117 (22). C16H16N2O4S (332.4): calcd. C 57.82, H
4.85, N 8.43; found C 57.74, H 4.71, N 8.22.
CH=CH2), 6.81 (t, J = 7.5 Hz, 1 H, 4-ArH), 7.00 (d, J = 7.8 Hz,
2 H, 3,5-ArH) ppm. 13C NMR (63 MHz, CDCl3): δ = 18.7 (2 C,
CH3), 35.3 (NCH2CH2), 47.4 (NCH2), 117.1 (CH=CH2), 121.7
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Bicyclic Sultams with Cyclopropane Moieties
(CH-Ar), 128.9 (2 C, CH-Ar), 129.2 (2 C, C-Ar), 136.2 (CH=CH2), (OCH3), 54.1 (CH2), 115.4 (CH=CH2), 128.5 (CH-Ar), 129.3 (2 C,
146.2 (C-Ar) ppm. MS (EI, 70 eV): m/z (%) = 175 (8) [M+], 134
(100), 105 (12).
N-(Pent-4-enyl)aniline (12a):[17] Yield 5.47 g (86%), colorless oil.
CH-Ar), 129.7 (2 C, CH-Ar), 137.4 (CH=CH2), 138.4 (C-Ar), 164.0
(CO) ppm. MS (EI, 70 eV): m/z (%) = 297 (1) [M+], 242 (28), 160
(78), 118 (21), 106 (100), 77 (26), 55 (10).
General Procedure for the Synthesis of Sultams 17, 19 (GP5): A
solution of bromine (3.40 g, 23.0 mmol) in CH2Cl2 (20 mL) was
slowly added at 0 °C to a solution of the respective sulfonamide
13, 14 or 15 (22.0 mmol) in CH2Cl2 (70 mL), and the mixture was
stirred for an additional 30 min, then washed with water (30 mL),
10% Na2SO3 (2ϫ30 mL), brine (30 mL) and dried with anhydrous
Na2SO4. The solvents were removed in vacuo with a rotary evapo-
rator, and the crude dibromide was used in the next step without
any additional purification.
General Procedure for the Synthesis of Methyl 2-(N-Alkenyl-N-aryl-
sulfamoyl)acetates 13–15 (GP4): A solution of methyl (chlorosulfo-
nyl)acetate (5.18 g, 30.0 mmol) in anhydrous acetonitrile (30 mL)
was slowly added at 10 °C to a solution of the respective alkenylani-
line (33.0 mmol) and pyridine (2.84 g, 36.0 mmol) in anhydrous
acetonitrile (75 mL). Then the reaction mixture was stirred at 30 °C
for 1 h, diluted with water (250 mL), acidified with concentrated
HCl to pH 2 and extracted with CH2Cl2 (3ϫ75 mL). The com-
bined organic phases were washed with 5% HCl (2ϫ50 mL), brine
(50 mL) and dried with anhydrous MgSO4. The solvents were re-
moved in vacuo with a rotary evaporator, and the corresponding
sulfonamide was used in the next step without purification. Ac-
cording to GP4 the following sulfonamides were prepared:
A solution of the respective dibromide 16, 18 or 20 (22.0 mmol) in
DMF (50 mL) was added at 50 °C within 3 h to a suspension of
K2CO3 (9.52 g, 69.0 mmol) in DMF (100 mL) , and the mixture
was stirred at this temperature for an additional 1 h. Then the
DMF was removed in vacuo, the residue dissolved in CH2Cl2
(150 mL), the solution washed with water (75 mL) and 10% HCl
(3ϫ75 mL), water (50 mL) and brine (50 mL). The organic phase
was dried with anhydrous MgSO4 and concentrated in vacuo with
a rotary evaporator. The crude product was recrystallized from
EtOAc/hexane (the sultams 19a–e were purified by flash
chromatography) to give the corresponding methyl 3-aryl-2,2-di-
oxo-2-thia-3-azabicyclo[n.1.0]alkane-1-carboxylate. According to
GP5 the following sultams were prepared.
Methyl 2-(N-Allyl-N-phenylsulfamoyl)acetate (13a):[1] Yield 5.97 g
(74%), slightly yellow oil, Rf = 0.32 (EtOAc/hexane, 1:2).
Methyl 2-[N-Allyl-N-(4-methylphenyl)sulfamoyl]acetate (13b): Yield
6.23 g (73%), slightly yellow oil, Rf = 0.34 (EtOAc/hexane, 1:2). 1H
NMR (300 MHz, CDCl3): δ = 2.36 (s, 3 H, CCH3), 3.83 (s, 3 H,
OCH3), 3.98 (s, 2 H, SO2CH2), 4.32 (dt, J = 1.2, 6.3 Hz, 2 H,
NCH2), 5.07–5.15 (m, 2 H, CH=CH2), 5.79 (ddt, J = 6.3, 10.2,
16.5 Hz, 1 H, CH=CH2), 7.19–7.22 (m, 2 H, ArH), 7.30–7.34 (m,
2 H, ArH) ppm. 13C NMR (75 MHz, CDCl3): δ = 21.0 (CCH3),
53.0 (OCH3), 54.3 (CH2), 55.4 (CH2), 118.7 (CH=CH2), 129.0 (2
C, CH-Ar), 130.0 (2 C, CH-Ar), 133.1 (CH=CH2), 135.5 (C-Ar),
138.4 (C-Ar), 163.9 (CO) ppm. MS (EI, 70 eV): m/z (%) = 283 (75)
[M+], 252 (18), 145 (100), 130 (95), 119 (61), 105 (46), 91 (96), 77
(56), 65 (95), 41 (95).
Methyl 2,2-Dioxo-3-phenyl-2-thia-3-azabicyclo[3.1.0]hexane-1-car-
boxylate (17a): Yield 4.70 g (80%), colorless solid, m.p. 108–
109 °C. 1H NMR (300 MHz, CDCl3): δ = 1.89 (dd, J = 5.7, 8.2 Hz,
1 H, 6-H), 2.12 (t, J = 5.8 Hz, 1 H, 6Ј-H), 2.68 (m, 1 H, 5-H), 3.65
(d, J = 9.7 Hz, 1 H, 4-H), 3.91 (s, 3 H, OCH3), 3.98 (dd, J =
3.5, 9.7 Hz, 1 H, 4Ј-H), 7.20–7.42 (m, 5 H, ArH) ppm. 13C NMR
(75 MHz, CDCl3): δ = 19.3 (C-6), 22.8 (C-5), 42.5 (C-1), 45.7 (C-
4), 53.5 (OCH3), 123.1 (2 C, CH-Ar), 126.4 (CH-Ar), 129.4 (2 C,
CH-Ar), 136.2 (C-Ar), 165.7 (CO) ppm. MS (EI, 70 eV): m/z (%)
= 267 (38) [M+], 144 (27), 104 (74), 91 (13), 77 (100), 59 (15), 51
(36), 39 (31). C12H13NO4S (267.3): calcd. C 53.92, H 4.90, N 5.24;
found C 54.00, H 5.00, N 5.24.
Methyl 2-[N-(But-3-enyl)-N-phenylsulfamoyl]acetate (14a): Yield
5.66 g (65%), colorless oil, Rf = 0.37 (EtOAc/hexane, 1:2). 1H
NMR (250 MHz, CDCl3): δ = 2.21 (q, J = 7.1 Hz, 2 H,
NCH2CH2), 3.78–3.84 (m, 5 H), 3.94 (s, 2 H, SO2CH2), 5.00–5.07
(m, 2 H, CH=CH2), 5.65–5.81 (m, 1 H, CH=CH2), 7.36–7.47 (m,
5
H, ArH) ppm. 13C NMR (63 MHz, CDCl3):
δ = 33.4
(NCH2CH2), 52.2 (CH2), 53.2 (OCH3), 54.2 (CH2), 117.5
(CH=CH2), 128.6 (CH-Ar), 129.5 (2 C, CH-Ar), 129.7 (2 C, CH-
Ar), 134.4 (CH=CH2), 138.2 (C-Ar), 164.1 (CO) ppm. MS (EI,
70 eV): m/z (%) = 283 (2) [M+], 242 (64), 146 (10), 118 (18), 105
(100), 77 (72), 51 (24), 41 (36).
Methyl 3-(4-Methylphenyl)-2,2-dioxo-2-thia-3-azabicyclo[3.1.0]hex-
ane-1-carboxylate (17b): Yield 5.06 g (83%), slightly yellow solid,
1
m.p. 125–126 °C. H NMR (300 MHz, CDCl3): δ = 1.86 (dd, J =
5.8, 8.1 Hz, 1 H, 6-H), 2.10 (t, J = 5.8 Hz, 1 H, 6Ј-H), 2.33 (s, 3
H, CCH3), 2.65 (ddd, J = 3.6, 6.1, 8.0 Hz, 1 H, 5-H), 3.58 (d, J =
9.7 Hz, 1 H, 4-H), 3.89 (s, 3 H, OCH3), 3.93 (dd, J = 3.4, 9.7 Hz,
1 H, 4Ј-H), 7.15–7.23 (m, 4 H, ArH) ppm. 13C NMR (75 MHz,
CDCl3): δ = 19.3 (C-6), 20.8 (CH3), 22.8 (C-5), 42.2 (C-1), 46.0 (C-
4), 53.4 (OCH3), 123.7 (2 C, CH-Ar), 129.9 (2 C, CH-Ar), 133.2
(C-Ar), 136.6 (C-Ar), 165.7 (CO) ppm. MS (EI, 70 eV): m/z (%) =
281 (100) [M+], 158 (35), 91 (72), 65 (26), 39 (20). C13H15NO4S
(281.3): calcd. C 55.47, H 5.57, N 4.89; found C 55.50, H 5.37, N
4.98.
Methyl 2-[N-(But-3-enyl)-N-(4-methylphenyl)sulfamoyl]acetate (14b):
Yield 6.24 g (70%), colorless oil, Rf = 0.38 (EtOAc/hexane, 1:2).
1H NMR (250 MHz, CDCl3): δ = 2.16–2.25 (m, 2 H, NCH2CH2),
2.37 (s, 3 H, CCH3), 3.78 (t, J = 7.0 Hz, 2 H, NCH2), 3.82 (s, 3 H,
OCH3), 3.94 (s, 2 H, SO2CH2), 4.97–5.06 (m, 2 H, CH=CH2), 5.64–
5.81 (m, 1 H, CH=CH2), 7.19–7.23 (m, 2 H, ArH), 7.32–7.36 (m,
2 H, ArH) ppm. 13C NMR (63 MHz, CDCl3): δ = 21.2 (CCH3),
33.4 (NCH2CH2), 52.2 (CH2), 53.2 (OCH3), 54.1 (CH2), 117.4
(CH=CH2), 129.2 (2 C, CH-Ar), 130.3 (2 C, CH-Ar), 134.4
(CH=CH2), 135.5 (C-Ar), 138.7 (C-Ar), 164.1 (CO) ppm. MS (EI,
70 eV): m/z (%) = 297 (4) [M+], 256 (100), 119 (90), 91 (14).
Methyl 2,2-Dioxo-3-phenyl-2-thia-3-azabicyclo[4.1.0]heptane-1-car-
boxylate (19a): Yield 6.65 g (63%), colorless solid, m.p. 120–121 °C,
1
Methyl 2-[N-(Pent-4-enyl)-N-phenylsulfamoyl]acetate (15a): Yield
6.24 g (70%), colorless oil, Rf = 0.42 (EtOAc/hexane, 1:2). 1H
NMR (250 MHz, CDCl3): δ = 1.57 (quintett, J = 7.3 Hz, 2 H,
NCH2CH2), 2.02–2.12 (m, J = 7.3 Hz, 2 H, NCH2CH2CH2), 3.75
(t, J = 7.2 Hz, 2 H, NCH2) 3.82 (s, 3 H, OCH3), 3.94 (s, 2 H,
Rf = 0.14 (EtOAc/hexane, 1:2). H NMR (250 MHz, CDCl3): δ =
1.76 (dd, J = 5.6, 9.4 Hz, 1 H, 7-H), 1.87 (dd, J = 5.6, 7.5 Hz, 1
H, 7Ј-H), 2.22–2.56 (m, 3 H), 3.58 (ddd, J = 5.1, 7.3, 13.5 Hz, 1 H,
4-H), 3.87 (s, 3 H, OCH3), 4.10 (ddd, J = 6.4, 8.2, 13.5 Hz, 1 H,
4Ј-H), 7.22–7.39 (m, 5 H, ArH) ppm. 13C NMR (63 MHz, CDCl3):
SO2CH2), 4.91–5.00 (m, 2 H, CH=CH2), 5.72 (ddt, J = 6.6, 10.2, δ = 19.9 (C-6), 22.5 (C-5), 27.3 (C-6), 44.5 (C-1), 49.8 (C-4), 53.5
16.8 Hz, 1 H, CH=CH2), 7.31–7.49 (m, 5 H, ArH) ppm. 13C NMR
(OCH3), 126.2 (2 C, CH-Ar), 127.1 (CH-Ar), 129.2 (2 C, CH-Ar),
(63 MHz, CDCl3): δ = 28.1 (CH2), 30.4 (CH2), 52.3 (CH2), 53.2 140.4 (C-Ar), 167.8 (CO) ppm. MS (EI, 70 eV): m/z (%) = 281 (36)
Eur. J. Org. Chem. 2009, 2635–2641
© 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
2639

V. V. Sokolov, A. de Meijere et al.
FULL PAPER
[M+], 105 (100), 77 (10). C13H15NO4S (281.3): calcd. C 55.50, H
5.37, N 4.98; found C 55.49, H 5.33, N 5.25.
7), 23.0 (C-5), 26.7 (C-6), 41.5 (C-1), 41.7 (C-4), 53.5 (OCH3), 168.1
(CO) ppm. MS (EI, 70 eV): m/z (%) = 205 (26) [M+], 177 (20),
174 (28), 145 (40), 126 (16), 113 (100), 112 (44), 81 (56), 53 (41).
C7H11NO4S (205.2): calcd. C 40.97, H 5.40, N 6.82; found C 41.30,
H 5.16, N 6.99.
Methyl 3-(4-Methylphenyl)-2,2-dioxo-2-thia-3-azabicyclo[4.1.0]hep-
tane-1-carboxylate (19b): Yield 3.25 g (54%), colorless solid, m.p.
74–75 °C, Rf = 0.18 (EtOAc/hexane, 1:2). 1H NMR (250 MHz,
CDCl3): δ = 1.77 (dd, J = 5.7, 9.7 Hz, 1 H, 7-H), 1.92 (dd, J = 5.7,
7.6 Hz, 1 H, 7Ј-H), 2.18–2.52 (m, 3 H), 2.33 (s, 3 H, CCH3), 3.49
(ddd, J = 5.2, 7.1, 13.6 Hz, 1 H, 4-H), 3.86 (s, 3 H, OCH3), 4.11
(ddd, J = 6.3, 8.2, 13.6 Hz, 1 H, 4Ј-H), 7.12–7.22 (m, 4 H, ArH)
ppm. 13C NMR (63 MHz, CDCl3): δ = 19.7 (C-7), 20.9 (CH3), 22.4
(C-5), 27.2 (C-6), 44.5 (C-1), 49.9 (C-4), 53.5 (OCH3), 126.3 (2 C,
CH-Ar), 129.9 (2 C, CH-Ar), 137.2 (C-Ar), 137.7 (C-Ar), 167.9
(CO) ppm. MS (EI, 70 eV): m/z (%) = 295 (68) [M+], 119 (100), 91
(20). C14H17NO4S (295.4): calcd. C 56.93, H 5.80, N 4.74; found
C 56.90, H 5.71, N 4.91.
Methyl 2,2-Dioxo-1,2-thiazolidine-5-carboxylate (26): Yield 269 mg
(75%), colorless solid, m.p. 110–111 °C. 1H NMR (250 MHz, [D6]-
DMSO): δ = 2.36–2.61 (m, 2 H), 3.02–3.26 (m, 2 H), 3.73 (s, 3 H,
OCH3), 4.02 (dd, J = 7.2, 8.8 Hz, 1 H, 6-H), 7.06 (t, J = 7.0 Hz, 1
H, NH) ppm. 13C NMR (250 MHz, [D6]DMSO): δ = 28.1 (C-4),
39.7 (C-3), 52.6 (OCH3), 60.8 (C-5), 165.7 (CO) ppm. MS (DCI):
m/z = 197 [M + NH4+]. C5H9NO4S (179.2): calcd. C 33.51, H 5.06,
N 7.82; found C 33.71, H 4.78, N 8.07.
Methyl 2,2-Dioxo-1,2-thiazinane-6-carboxylate (28): Yield 656 mg
(68%), colorless solid, m.p. 104–105 °C. 1H NMR (250 MHz, [D6]-
DMSO): δ = 1.52–1.75 (m, 2 H), 2.15–2.26 (m, 2 H), 3.17–3.25 (m,
2 H), 3.76 (s, 3 H, OCH3), 3.89 (dd, J = 5.5, 9.3 Hz, 1 H, 6-H),
7.00 (t, J = 7.1 Hz, 1 H, NH) ppm. 13C NMR (250 MHz, [D6]-
DMSO): δ = 22.9 (CH2), 26.7 (CH2), 44.4 (C-3), 52.1 (OCH3), 62.9
(C-6), 165.5 (CO) ppm. MS (DCI): m/z = 211 [M + NH4+].
C6H11NO4S (193.2): calcd. C 37.30, H 5.74, N 7.25; found C 37.63,
H 5.50, N 7.04.
t-2-Methoxycarbonyl-2-sulfamoyl-r-1-cyclopropanecarboxylic Acid
(22): Periodic acid (6.81 g, 30 mmol) and RuCl3·nH2O (27 mg,
0.09 mmol, 3 mol-%) were added to a solution of the sultam 17e
(891 mg, 3 mmol) in a mixture of CH2Cl2 (15 mL), MeCN (15 mL)
and H2O (25 mL), and the mixture was stirred vigorously at room
temp. for 10 h. The reaction mixture was extracted with EtOAc
(3ϫ30 mL), the combined organic phases were dried with MgSO4
and filtered through a short pad of silica gel. The solvents were
removed in vacuo with a rotary evaporator, and the solid residue
was recrystallized from EtOAc/hexane to afford the carboxylic acid
Acknowledgments
1
22 (615 mg, 92%) as a colorless solid, m.p. 142–144 °C. H NMR
(250 MHz, [D6]DMSO): δ = 1.78 (dd, J = 5.8, 8.0 Hz, 1 H, 3-H),
1.95 (dd, J = 5.8, 7.7 Hz, 1 H, 3Ј-H), 1.85 (t, J = 7.8 Hz, 1 H, 1-
H), 3.78 (s, 3 H, OCH3), 6.85 (s, 2 H, NH2) ppm. 13C NMR
(250 MHz, [D6]DMSO): δ = 18.3 (CH), 31.1 (CH), 48.2 (C), 53.3
(OCH3), 167.0 (NH CO), 167.3 (CO) ppm. MS (ESI): m/z (%) =
445 [2 M – H+], 222 (100) [M – H+]. C6H9NO6S (223.2): calcd. C
32.29, H 4.06, N 6.28; found C 31.98, H 3.84, N 6.21.
This work was supported by the Land Niedersachsen and by Bayer
CropScience AG. The authors are grateful to Dr. Heiko Schill for
technical assistance in assembling the final manuscript.
[1] V. A. Rassadin, A. A. Tomashevskiy, V. V. Sokolov, A. A. Pote-
khin, Khim. Geterosikl. Soedin. 2008, 605–617; Chem. Hetero-
cycl. Compd. Engl. Transl. 2008, 44, 474–485.
[2] G. H. Wee, B. Liu, L. Zhang, J. Org. Chem. 1992, 57, 4404–
4414.
General Procedure for the Oxidative Cleavage of the 4-Meth-
oxyphenyl Group with Ceric Ammonium Nitrate (CAN) (GP6): A
solution of CAN (12.08 g, 22.05 mmol) in water (80 mL) was
slowly added to a stirred solution of the respective sultam (7 mmol)
in MeCN (100 mL) kept at 0 °C, and the mixture was stirred for
an additional 1 h, then diluted with water (200 mL) and extracted
with EtOAc (5ϫ50 mL). The organic phase was washed with 10%
Na2SO3 (100 mL), water (50 mL), brine (50 mL) and dried with
MgSO4. The solvents were evaporated in vacuo with a rotary evap-
orator, and the crude product was purified by flash chromatog-
raphy followed by recrystallization from EtOAc/hexane. According
to GP6 the following sultams were prepared:
[3] Crystals of methyl 2,2-dioxo-3-phenyl-2-thia-3-azabicy-
clo[3.1.0]hexane-1-carboxylate (17a) were grown by slow evap-
oration of their solution in a CH2Cl2/Et2O/hexane mixture and
measured on a Stoe IPDS II two circle diffractometer using
graphite-monochromated Mo-Kα radiation. The structure solu-
tions and refinements on F2 were performed with the
SHELXL-97 program. The hydrogen atoms were located in dif-
ference Fourier maps and refined as riding groups with the 1.2-
fold isotropic displacement parameter of the corresponding C
atom. 17a: C12H13NO4S (267.29), crystal size: 0.1–0.3 mm, T
133(2) K, monoclinic, a = 10.3899(7), b = 6.0821(3), c =
19.3059(15) Å, α = 90, β = 104.531(6), γ = 90°, V =
1180.96(13) Å3, Z = 4, space group P21/n, ρ = 1.503 gcm–3, µ
= 0.280 mm–1, intensities measured: 17057 (2θmax = 49.52°),
independent 1982 (Rint = 0.0339), 215 parameters refined, R1
= 0.0279 for 1896 reflections with IϾ2σ(I), wR2 (all data) =
0.0691, Gof = 1.076, maximum and minimum residual electron
densities 0.347 and –0.294 eÅ–3. CCDC-713449 contains the
crystallographic data (excluding structure factors). These data
can be obtained free of charge from The Cambridge Crystallo-
graphic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
[4] See e.g.: S. I. Kozhushkov, R. Langer, D. S. Yufit, J. A. K.
Howard, H. Schill, D. Demus, K. Miyazawa, A. de Meijere,
Eur. J. Org. Chem. 2004, 289–303.
Methyl
2,2-Dioxo-2-thia-3-azabicyclo[3.1.0]hexane-1-carboxylate
(23): Yield 1.04 g (78%); colorless solid, m.p. 119–120 °C; Rf = 0.08
1
(EtOAc/hexane, 1:2). H NMR (250 MHz, CDCl3): δ = 1.74 (t, J
= 6.6 Hz, 1 H, 6-H), 1.86 (t, J = 7.3 Hz, 1 H, 6Ј-H), 2.58–2.65 (m,
1 H, 5-H), 3.33 (dd, J = 6.4, 12.4 Hz, 1 H, 4-H), 3.52 (ddd, J =
3.1, 8.2, 12.3 Hz, 1 H, 4Ј-H), 3.86 (s, 3 H, OCH3), 4.79 (t, J =
6.2 Hz, 1 H, NH) ppm. 13C NMR (63 MHz, CDCl3): δ = 22.7 (C-
6), 28.8 (C-5), 40.6 (C-4), 42.9 (C-1), 53.5 (OCH3), 166.2 (CO)
ppm. MS (EI, 70 eV): m/z (%) = 191 (100) [M+], 160 (58), 126 (16),
95 (96), 67 (72), 59 (30), 41 (54). C6H9NO4S (191.2): calcd. C 37.69,
H 4.74, N 7.33; found C 37.91, H 4.57, N 7.09.
Methyl 2,2-Dioxo-2-thia-3-azabicyclo[4.1.0]heptane-1-carboxylate
(24): Yield 554 mg (89%), slightly yellow solid, m.p. 108–109 °C.
1H NMR (250 MHz, CDCl3): δ = 1.65–1.76 (m, 2 H), 1.85–1.98
(m, 1 H), 2.12–2.25 (m, 1 H), 2.39–2.50 (m, 1 H), 3.21–3.33 (m, 1
H), 3.44–3.60 (m, 1 H), 3.84 (s, 3 H, OCH3), 4.12 (dd, J = 4.8,
8.2 Hz, 1 H, NH) ppm. 13C NMR (63 MHz, CDCl3): δ = 20.0 (C-
[5] F. H. Allen, Acta Crystallogr., Sect. B 1980, 36, 81–96.
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12, 66–72.
[7] L. S. M. Miranda, M. L. A. A. Vasconcellos, Synthesis 2004,
11, 1767–1770.
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[14]
[15]
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[17]
Received: February 2, 2009
Published Online: April 15, 2009
Eur. J. Org. Chem. 2009, 2635–2641
© 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
2641