Arenesulfonylimines of methyl trifluoropyruvate in the cyclocondensation reactions with 1,3-C,N-and-N,N-binucleophiles

Article abstract of DOI:10.1007/s11172-007-0352-1

Reaction of arenesulfonylimines of methyl trifluoropyruvate with 1,3-C,N-and-N,N-binucleophiles led to a variety of N-sulfonylated fluorine-containing heterocycles, including the fused ones.

Full text of DOI:10.1007/s11172-007-0352-1

Russian Chemical Bulletin, International Edition, Vol. 56, No. 11, pp. 2247—2251, November, 2007
2247
Arenesulfonylimines of methyl trifluoropyruvate
in the cyclocondensation reactions with 1,3ꢀC,Nꢀ and ꢀN,Nꢀbinucleophiles

V. B. Sokolov, A. Yu. Aksinenko, and I. V. Martynov
Institute of Physiologically Active Compounds, Russian Academy of Sciences,
142432 Chernogolovka, Moscow Region, Russian Federation.
Fax: +7 (496) 524 9508. Eꢀmail: alaks@ipac.ac.ru
Reaction of arenesulfonylimines of methyl trifluoropyruvate with 1,3ꢀC,Nꢀ and ꢀN,Nꢀbiꢀ
nucleophiles led to a variety of Nꢀsulfonylated fluorineꢀcontaining heterocycles, including the
fused ones.
Key words: arenesulfonamides of methyl trifluoropyruvate, sulfonylimines, nitrile of
2ꢀaminocrotonic acid, 6ꢀaminouracils, Nꢀsubstituted 3ꢀaminocyclohexenones, benzamidine,
2ꢀaminothiazoline, Nꢀsubstituted ureas, 2,3ꢀdihydroꢀ1Нꢀpyrroles, hexahydroꢀ1Нꢀpyrꢀ
rolo[2,3ꢀd]pyrimidines, hexahydroꢀ1Нꢀindoles, 4,5ꢀdihydroꢀ1Нꢀimidazoles, tetrahydroꢀ
imidazo[2,1ꢀb]thiazoles, imidazolidines, cyclocondensation.
Sulfanylamide drugs, despite of the discovery of peniꢀ
cillin and other antibiotics, did not lose their value and in
number of cases are successfully used for the treatment of
infectious diseases. The nowadays used sulfanylamide
drugs significantly differ in their pharmacological paꢀ
rameters (absorption, accumulation in blood and organs
in bacteriostatic concentrations, surmounting of the
hematoencephalitic barrier, time of the removal from orꢀ
ganism, etc.), which is caused to a considerable extent by
the nature of the substituents at the nitrogen atom.1 The
variation of substituents at the nitrogen atom has been
and, apparently, remains the main approach to the chemiꢀ
cal design of sulfanylamides, including ones with fluoꢀ
rineꢀcontaining substituents.2,3 Below, we consider from
this point of view a developed by us approach to the
introduction of various heterocycles with fluorineꢀconꢀ
taining substituents at the nitrogen atom of arenesulfanylꢀ
amide molecules.
A systematic study of behavior of acylimines of methyl
trifluoropyruvate (MTFP) in the cyclocondensation reꢀ
action with 1,3ꢀbinucleophiles, which enabled us to proꢀ
pose an original approach to the synthesis of fiveꢀ and
sixꢀmembered heterocycles with fluorineꢀcontaining subꢀ
stituents, served as the prerequisite to this research.4—9
In the present work, new data on the synthetic potentialiꢀ
ties of arenesulfonylimines of MTFP 1 in the preparaꢀ
tion of fluorineꢀcontaining Nꢀarenesulfonylated heteroꢀ
cycles by the cyclocondensation of compounds 1 with
1,3ꢀC,Nꢀ and ꢀN,Nꢀbinucleophiles are presented. It
should be noted that earlier, sulfonylimines of polyfluoroꢀ
ketones were used in the synthesis of heterocycles with
fluorineꢀcontaining substituents (the azaꢀDiels—Alder
reaction),10 as well as of biologically active fluorineꢀconꢀ
taining aminophosphonates, the serine hydrolase inꢀ
hibitors.11
In contrast to acylimines of MTFP, showing properꢀ
ties of 1,2ꢀ and 1,3ꢀbielectrophiles in the cycloconꢀ
densation reactions, arenesulfonylimines of MTFP 1 exꢀ
clusively play the role of 1,2ꢀbielectrophiles in the reꢀ
actions with 1,3ꢀbinucleophiles. These transformations,
similarly to the reactions studied by us earlier,5,7—9 proꢀ
ceed according to the twoꢀstep scheme: addition of the
binucleophile at the C=N bond of arenesulfonylimine
and subsequent cyclization with elimination of МеОН.
In the cyclocondensation with compounds 1a—d, niꢀ
trile of 2ꢀaminocrotonic acid (2), 6ꢀaminouracils 3a,b,
and Nꢀsubstituted 3ꢀaminocyclohexenones 4a—d were
studied as the C,Nꢀbinucleophiles, whereas benzamiꢀ
dine 5, 2ꢀaminothiazoline 6, and Nꢀsubstituted ureas
7a—d, as the N,Nꢀbinucleophiles (Scheme 1). The reacꢀ
tion was carried out by the heating of a mixture of reꢀ
agents in DMF for 1 h at 90—100 °С and, in case of
nucleophiles 3, 4, and 7, in the presence of catalytic
amount of Et3N. All the transformations considered above
led to the formation of the corresponding Nꢀarenesulꢀ
fonylated heterocycles with fluorineꢀcontaining substituꢀ
ents: 2,3ꢀdihydroꢀ1Нꢀpyrroles 8a—c, 2,3,4,5,6,7ꢀhexaꢀ
hydroꢀ1Нꢀpyrrolo[2,3ꢀd]pyrimidines 9a,b, 2,3,4,5,6,7ꢀ
hexahydroꢀ1Нꢀindoles 10a—d, 4,5ꢀdihydroꢀ1Нꢀimidꢀ
azoles 11a,b, 2,3,5,6ꢀtetrahydroimidazo[2,1ꢀb]thiazoles
12a,b, and imidazolidines 13a—e.
Amidosulfonates 8a—c, 9a,b, 10a—d, 11a,b, 12a,b,
and 13a—e, obtained in 65—81% yield, are solid crystalꢀ
line substances. Their composition and structures were
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2171—2175, November, 2007.
1066ꢀ5285/07/5611ꢀ2247 © 2007 Springer Science+Business Media, Inc.

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Russ.Chem.Bull., Int.Ed., Vol. 56, No. 11, November, 2007
Sokolov et al.
Scheme 1
1, 8: R = H (a), MeO (b), Cl (c), Me (d)
3, 9: R´ = CH2Ph (a), 4ꢀClC6H4 (b)
4: R´ = 3,4ꢀMe2C6H3 (a), CH2Ph (b),
(c), CH2CH2Ph (d)
7: R´ = CH2Ph (a), 4ꢀClC6H4 (b), Ph (c), 4ꢀFC6H4 (d)
10: R = H, R´ = 3,4ꢀMe2C6H3 (a); R = Me, R´ = CH2Ph (b); R = Me, R´ =
(c); R = Cl, R´ = CH2CH2Ph (d)
11: R = H (a), Cl (b)
12: R = H (a), MeO (b)
13: R = H, R´ = CH2Ph (a); R = Me, R´ = CH2Ph (b); R = Me, R´ = 4ꢀClC6H4 (c); R = Cl, R´ = Ph (d); R = H, R´ = 4ꢀFC6H4 (e)
confirmed by elemental analysis and NMR spectroscopy
data. In the 19F NMR spectra, signals of the trifluoroꢀ
methyl groups in the region δ –1—5 is characteristic
of them.
It should be noted that in the transformations under
consideration (taking into account the high electrophilicꢀ
ity of the C=N bond of the arenesulfonylimines of MTFP,
which exothermically react with C,Hꢀ and N,Hꢀnucleoꢀ

Methyl trifluoropyruvate arenesulfonylimines
Russ.Chem.Bull., Int.Ed., Vol. 56, No. 11, November, 2007 2249
philes),12,13 the condensation is the determining step,
rather than the Сꢀalkylation, and these processes are unꢀ
der the decisive influence of the nucleophilic properties
of the addition products of arenesulfonylimines of MTFP
to 1,3ꢀbinucleophiles. Thus, the cyclocondensation with
the least nucleophilic binucleophiles (3, 4, and 7) was
successful only in the presence of catalytic amount
of Et3N.
In conclusion, starting from the fairly available areneꢀ
sulfonylimines of MTFP, we synthesized a variety of the
earlier unknown Nꢀarenesulfonylated fluorineꢀcontainꢀ
ing 2,3ꢀdihydroꢀ1Нꢀpyrroles, imidazoles, and imidꢀ
azolidines, including the fused ones, which can be of
interest as the potentially biologically active substances.
Experimental
1
H and 19F NMR spectra were recorded on a Bruker
DXP 200 spectrometer (200.13 and 188.29 MHz) relatively
to Me4Si and CF3COOH as the internal and external
standards, respectively. Melting points were determined in
a glass capillary tube on a PTP (M) instrument and were uncorꢀ
rected. The starting arenesulfonylimines of MTFP 1a—d were
synthesized according to the procedure described earlier,14
6ꢀaminouracils 3a,b, according to the known procedure,15
Nꢀsubstituted 3ꢀaminocyclohexenones 4a—d, according to the
published procedure.16 Nitrile of 2ꢀaminocrotonic acid 2,
benzamidine 5, 2ꢀaminothiazoline 6, and Nꢀsubstituted ureas
7a—d (all from Aldrich) were used without additional purifiꢀ
cation.
Table 1. The yields, melting points, and elemental analysis data of compounds 8a—c, 9a,b, 10a—d,
11a,b, 12a,b, and 13a—e
Comꢀ
pound
Yield
(%)
M.p./°С
Found
Calculated
Molecular
formula
(%)
C
H
N
8a
81
76
65
75
77
73
72
69
73
68
76
70
67
66
73
74
68
67
133—135
145—147
151—153
168—170
134—136
137—139
141—143
139—141
166—168
217—219
176—178
185—187
165—167
169—171
133—135
148—150
156—158
159—161
45.07
45.22
44.93
44.80
41.34
41.12
50.12
50.00
45.69
45.57
59.41
59.28
59.41
59.28
56.93
56.80
55.63
55.51
50.30
50.13
40.12
40.00
39.31
39.45
39.38
39.49
49.52
49.40
50.44
50.58
45.48
45.60
44.19
44.30
46.17
46.05
2.79
2.92
3.33
3.22
2.23
2.39
3.02
3.15
2.55
2.42
4.85
4.97
4.83
4.97
4.88
4.77
4.59
4.47
3.02
3.16
2.78
2.65
2.62
2.76
3.21
3.06
3.29
3.41
3.89
3.77
2.81
2.93
2.71
2.56
2.78
2.66
12.03
12.17
11.36
11.20
11.19
11.07
11.49
11.66
11.32
11.19
5.66
5.53
5.38
5.53
8.14
8.28
5.02
5.18
10.81
10.96
10.18
10.06
11.34
11.50
10.48
10.63
10.03
10.17
9.71
9.83
9.52
9.38
9.55
9.56
10.21
10.07
C13H10F3N3O3S
C14H12F3N3O4S
C13H9ClF3N3O3S
C20H15F3N4O5S
C19H12ClF3N4O5S
C25H25F3N2O4S
C25H25F3N2O4S
C24H24F3N3O4S
C25H24ClF3N2O4S
С16H12F3N3O3S
С16H11ClF3N3O3S
С12H10F3N3O3S2
С13H12F3N3O4S2
C17H14F3N3O4S
C18H16F3N3O3S
C17H13ClF3N3O4S
C16H11ClF3N3O4S
C16H11F4N3O4S
8b
8c
9a
9b
10a
10b
10c
10d
11a
11b
12a
12b
13a
13b
13c
13d
13e

2250
Russ.Chem.Bull., Int.Ed., Vol. 56, No. 11, November, 2007
Sokolov et al.
Nꢀ(4ꢀCyanoꢀ5ꢀmethylꢀ2ꢀoxoꢀ3ꢀtrifluoromethylꢀ2,3ꢀdihydroꢀ
1Нꢀpyrrolꢀ3ꢀyl)benzenesulfonamide (8a), Nꢀ(4ꢀcyanoꢀ5ꢀmethylꢀ
2ꢀoxoꢀ3ꢀtrifluoromethylꢀ2,3ꢀdihydroꢀ1Нꢀpyrrolꢀ3ꢀyl)ꢀ4ꢀ
methoxybenzenesulfonamide (8b), Nꢀ(4ꢀcyanoꢀ5ꢀmethylꢀ2ꢀoxoꢀ
3ꢀtrifluoromethylꢀ2,3ꢀdihydroꢀ1Нꢀpyrrolꢀ3ꢀyl)ꢀ4ꢀchlorobenzeneꢀ
sulfonamide (8c), Nꢀ(5ꢀoxoꢀ2ꢀphenylꢀ4ꢀtrifluoromethylꢀ4,5ꢀ
dihydroꢀ1Нꢀimidazolꢀ4ꢀyl)benzenesulfonamide (11a), Nꢀ(5ꢀoxoꢀ
2ꢀphenylꢀ4ꢀtrifluoromethylꢀ4,5ꢀdihydroꢀ1Нꢀimidazolꢀ4ꢀyl)ꢀ4ꢀ
chlorobenzenesulfonamide (11b), Nꢀ(5ꢀoxoꢀ6ꢀtrifluoromethylꢀ
2,3,5,6ꢀtetrahydroimidazo[2,1ꢀb]thiazolꢀ6ꢀyl)benzenesulfonꢀ
amide (12a), and Nꢀ(5ꢀoxoꢀ6ꢀtrifluoromethylꢀ2,3,5,6ꢀtetraꢀ
hydroimidazo[2,1ꢀb]thiazolꢀ6ꢀyl)ꢀ4ꢀmethoxybenzenesulfonamide
(12b) (general procedure). A solution of the corresponding
arenesulfonylimine of MTFP 1 (0.01 mol) and the correspondꢀ
ing binucleophile 2, 5, or 6 (0.01 mol) in DMF (10 mL) was
stirred for 1 h at 20 °C and heated for 2 h at 90—100 °C. Then,
the reaction mixture was cooled, poured in water (50 mL),
the precipitate formed was filtered off and recrystallized from
50% aq. EtOH. The yields, melting points, and spectral characꢀ
teristics of compounds 8a—c, 11a,b, and 12a,b are given in
Tables 1 and 2.
Nꢀ(1ꢀBenzylꢀ5ꢀtrifluoromethylꢀ2,4,6ꢀtrioxoꢀ2,3,4,5,6,7ꢀ
hexahydroꢀ1Нꢀpyrrolo[2,3ꢀd]pyrimidinꢀ5ꢀyl)benzenesulfonamide
(9a), Nꢀ{1ꢀ(4ꢀchlorophenyl)ꢀ5ꢀtrifluoromethylꢀ2,4,6ꢀtrioxoꢀ
2,3,4,5,6,7ꢀhexahydroꢀ1Нꢀpyrrolo[2,3ꢀd]pyrimidinꢀ5ꢀyl}benꢀ
zenesulfonamide (9b), Nꢀ[6,6ꢀdimethylꢀ1ꢀ(3,4ꢀdimethylphenyl)ꢀ
2,4ꢀdioxoꢀ3ꢀtrifluoromethylꢀ2,3,4,5,6,7ꢀhexahydroꢀ1Нꢀindolꢀ3ꢀ
yl]benzenesulfonamide (10a), Nꢀ(1ꢀbenzylꢀ6,6ꢀdimethylꢀ2,4ꢀ
dioxoꢀ3ꢀtrifluoromethylꢀ2,3,4,5,6,7ꢀhexahydroꢀ1Нꢀindolꢀ3ꢀyl)ꢀ
4ꢀmethylbenzenesulfonamide (10b), Nꢀ[6,6ꢀdimethylꢀ2,4ꢀdioxoꢀ
1ꢀ(pyridinꢀ3ꢀyl)methylꢀ3ꢀtrifluoromethylꢀ2,3,4,5,6,7ꢀhexahydroꢀ
1Нꢀindolꢀ3ꢀyl]ꢀ4ꢀmethylbenzenesulfonamide (10c), Nꢀ[6,6ꢀdiꢀ
methylꢀ2,4ꢀdioxoꢀ1ꢀ(2ꢀphenylethyl)ꢀ3ꢀtrifluoromethylꢀ
2,3,4,5,6,7ꢀhexahydroꢀ1Нꢀindolꢀ3ꢀyl]ꢀ4ꢀchlorobenzenesulfonꢀ
Table 2. 1Н and 19F NMR spectra of compounds 8a—c, 9a,b, 10a—d, 11a,b, 12a,b, and 13a—e in DMSOꢀd6
Compound
δ
(J/Hz)
δ
F
H
8a
8b
2.19 (s, 3 H, Me); 7.57 (m, 3 H, CHAr); 7.84 (m, 2 H, CHAr); 7.58 (s, 1 H, NH); 11.21 (s, 1 H, NH)
2.96 (s, 3 H, Me); 4.66 (s, 3 H, MeO); 7.78 (d, 2 H, CHAr, J = 9.8); 8.52 (d, 2 H, CHAr, J = 9.8);
10.15, 11.99 (both s, 1 H each, NH)
2.71 (s)
2.31 (s)
8c
9a
2.28 (s, 3 H, Me); 7.58, 7.81 (both d, 2 H each, CHAr, J = 8.5); 9.70, 11.29 (both s, 1 H each, NH)
5.17 (m, 2 Н, АВ system, J = 19); 7.36 (m, 7 H, CHAr); 7.51 (t, 1 H, J = 7.2); 7.64 (d, 2 H,
J = 7.2); 9.40, 10.71, 12.28 (all s, 1 H each, NH)
2.69 (s)
4.45 (s)
9b
7.40 (m, 2 H, CHAr); 7.51 (m, 3 H, CHAr); 7.59 (m, 2 H, CHAr); 7.81 (d, 2 H, CHAr, J = 8.3);
9.43, 10.82, 11.51 (all s, 1 H each, NH)
4.33 (s)
4.05 (s)
10a
10b
1.02, 1.08 (both s, 3 H each, Me); 2.15 (АВ system, 2 H, CH2, J = 10.6); 2.23, 2.38 (both s, 3 H each,
Me); 2.46 (s, 2 H, CH2); 7.18—7.36 (m, 5 H, CHAr); 7.73 (m, 3 H, CHAr); 9.83 (s, 1 H, NH)
1.05, 1.11 (both s, 3 H each, Me); 2.11 (АВ system, 2 H, CH2, J = 10.9); 2.36 (s, 3 H, Me);
2.49 (s, 2 H, CH2); 4.88 (s, 2 H, CH2N); 7.36 (m, 7 Н, CHAr); 7.95 (d, 2 H, CHAr, J = 8.1); 9.74
(s, 1 H, NH)
0.98, 1.06 (both s, 3 H each, Me); 2.15 (АВ system, 2 H, CH2, J = 10.6); 2.33 (s, 3 H, Me);
2.46 (s, 2 H, CH2); 4.88 (s, 2 H, CH2N); 7.36 (m, 6 Н, CHAr); 7.95 (d, 2 H, CHAr, J = 8.1); 9.74
(s, 1 H, NH)
4.62 (s)
4.51 (s)
10c
10d
0.96, 1.02 (both s, 3 H each, Me); 2.12 (s, 2 H, CH2); 2.16 (АВ system, 2 H, CH2, J = 17.4);
2.94 (m, 2 H, CH2); 3.84 (m, 2 H, CH2N); 7.22—7.38 (m, 5 H, CHAr); 7.46 (m, 2 H, CHAr);
7.94 (d, 2 H, CHAr, J = 8.4); 9.62 (s, 1 H, NH)
4.33 (s)
11a
11b
7.46 (m, 6 H, CHAr); 7.82 (m, 4 H, CHAr); 9.72, 12.20 (both br.s, 1 H each, NH)
7.44 (d, 2 H, CHAr, J = 8.3); 7.49 (m, 2 H, CHAr); 7.58 (m, 1 H, CHAr); 7.73, 7.84 (both d, 2 H each,
CHAr, J = 8.2); 9.80, 12.19 (both s, 1 H each, NH)
0.40 (s)
0.24 (s)
12a
12b
13a
13b
13c
13d
13e
3.81 (m, 3 H, CH2N + CH2S); 3.99 (m, 1 H, CH2S); 7.53 (m, 3 H, CHAr); 7.81 (m, 2 H, CHAr);
9.88 (s, 1 H, NH)
3.80 (m, 3 H, CH2N + CH2S); 3.87 (s, 3 H, MeO); 3.97 (m, 1 H, CH2S); 6.99, 7.81 (both d, 2 H each,
CHAr, J = 8.1); 9.77 (s, 1 H, NH)
4.58 (m, 2 Н, АВ system, J = 18.2); 7.27 (m, 5 H, CHAr); 7.53 (m, 3 H, CHAr); 7.77 (d, 2 H,
CHAr, J = 7.9); 9.78, 9.84 (both s, 1 H each, NH)
2.47 (s, 3 H, Me); 4.59 (m, АВ system, 2 H, J = 16.8); 7.31 (m, 7 H, CHAr); 7.65 (d, 2 H,
CHAr, J = 9.2); 9.70 (br.s, 2 H, NH)
2.47 (s, 3 H, Me); 7.34—7.55 (m, 6 H, CHAr); 7.77 (d, 2 H, CHAr, J = 8.6); 9.90, 10.09 (both s,
1 H each, NH)
7.31 (t, 2 H, CHAr, J = 7.9); 7.44 (m, 5 H, CHAr); 7.82 (d, 2 H, CHAr, J = 8.4); 9.82, 10.07 (both s,
1 H each, NH)
0.44 (s)
0.31 (s)
–0.48 (s)
–0.38 (s)
0.07 (s)
0.10 (s)
7.22 (t, 2 H, CHAr, J = 8.2); 7.34 (m, 2 H, CHAr); 7.58 (m, 3 H, CHAr); 7.87 (d, 2 H, CHAr
J = 8.2); 9.92, 9.97 (both s, 1 H each, NH)
,
0.02 (s,
3 F, CF3);
–31.52 (m,
1 F, CFAr
)

Methyl trifluoropyruvate arenesulfonylimines
Russ.Chem.Bull., Int.Ed., Vol. 56, No. 11, November, 2007 2251
amide (10d), Nꢀ[1ꢀbenzylꢀ2,3ꢀdioxoꢀ4ꢀ(trifluoromethyl)imidꢀ
azolidinꢀ4ꢀyl]benzenesulfonamide (13a), Nꢀ[1ꢀbenzylꢀ2,3ꢀdioxoꢀ
4ꢀ(trifluoromethyl)imidazolidinꢀ4ꢀyl]ꢀ4ꢀmethylbenzenesulfonꢀ
amide (13b), Nꢀ[1ꢀ(4ꢀchlorophenyl)ꢀ2,3ꢀdioxoꢀ4ꢀ(trifluoroꢀ
methyl)imidazolidinꢀ4ꢀyl]ꢀ4ꢀmethylbenzenesulfonamide (13c),
Nꢀ[2,5ꢀdioxoꢀ1ꢀphenylꢀ4ꢀ(trifluoromethyl)imidazolidinꢀ4ꢀyl]ꢀ4ꢀ
chlorobenzenesulfonamide (13d), and Nꢀ[2,5ꢀdioxoꢀ1ꢀ(4ꢀfluoroꢀ
phenyl)ꢀ4ꢀ(trifluoromethyl)imidazolidinꢀ4ꢀyl]benzenesulfonamide
(13e) (general procedure). A solution of the corresponding
arenesulfonylimine of MTFP 1 (0.01 mol) and the correspondꢀ
ing binucleophile 3a,b, 4a—d, or 7a—d (0.01 mol) in DMF
(10 mL) was stirred for 1 h at 20 °C, after that, Et3N (0.2 mL)
was added, and this was heated for 2 h at 90—100 °C. The
reaction mixture was cooled, poured in water (50 mL), the
precipitate formed was filtered off and recrystallized from
50% aq. EtOH. The yields, melting points, and spectral characꢀ
teristics of compounds 9a,b, 10a—d, and 13a—e are given in
Tables 1 and 2.
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54, 1667].
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This work was financially supported by the Russian
Academy of Sciences (Program "Biоmolecular and Meꢀ
dicinal Chemistry").
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Received June 28, 2007;
in revised form September 6, 2007