Synthesis of 2,3-dihydronaphtho[2,3-d][1,3]thiazole-4,9-diones and 2,3-dihydroanthra[2,3-d][1,3]thiazole-4,11-diones and novel ring contraction and fusion reaction of 3H-spiro[1,3-thiazole-2,1'-cyclohexanes] into 2,3,4,5-tetrahydro-1H-carbazole-6,11-diones

Article abstract of DOI:10.3762/bjoc.9.62

Treatment of N-substituted 2-(methylamino)naphthoquinones 3 and -anthracene-1,4-diones 4 with S2Cl2 and DABCO in chlorobenzene gave the corresponding 2,3-dihydronaphtho[2,3-d][1,3]thiazole-4,9-diones 1 and 2,3-dihydroanthra[2,3-d][1,3]thiazole-4,11-diones 2 by triethylamine addition, in high to moderate yields. The DABCO replacement for N-ethyldiisopropylamine in the reaction of anthracene-1,4-diones 4 led unexpectedly to the corresponding 2-thioxo-2,3-dihydroanthra[2,3-d][1,3]thiazole-4,11-diones 10. The reaction of 3H-spiro[1,3-thiazole-2,1'-cyclohexanes] 1d, 2d with Et3N in chlorobenzene under reflux yielded 2,3,4,5-tetrahydro-1H-carbazole-6,11-diones 15, 16, i.e., ring contraction and fusion products. A plausible mechanism was proposed for the formation of the products.

Full text of DOI:10.3762/bjoc.9.62

Synthesis of 2,3-dihydronaphtho[2,3-d][1,3]thiazole-
4,9-diones and 2,3-dihydroanthra[2,3-d][1,3]thiazole-
4,11-diones and novel ring contraction and fusion
reaction of 3H-spiro[1,3-thiazole-2,1'-cyclohexanes]
into 2,3,4,5-tetrahydro-1H-carbazole-6,11-diones
Lidia S. Konstantinova, Kirill A. Lysov, Ljudmila I. Souvorova
and Oleg A. Rakitin*
Full Research Paper
Open Access
Address:
Beilstein J. Org. Chem. 2013, 9, 577–584.
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of
Sciences, Leninsky Prospect, 47, 119991 Moscow, Russia
doi:10.3762/bjoc.9.62
Received: 11 January 2013
Accepted: 26 February 2013
Published: 19 March 2013
Email:
Oleg A. Rakitin* - orakitin@ioc.ac.ru
* Corresponding author
Associate Editor: J. P. Wolfe
Keywords:
© 2013 Konstantinova et al; licensee Beilstein-Institut.
License and terms: see end of document.
anthracene-1,4-diones; 1H-carbazole-6,11-diones; fused thiazoles;
fusion reaction; heterocycles; naphthoquinones; ring contraction;
sulfur–nitrogen
Abstract
Treatment of N-substituted 2-(methylamino)naphthoquinones 3 and -anthracene-1,4-diones 4 with S2Cl2 and DABCO in chloroben-
zene gave the corresponding 2,3-dihydronaphtho[2,3-d][1,3]thiazole-4,9-diones 1 and 2,3-dihydroanthra[2,3-d][1,3]thiazole-4,11-
diones 2 by triethylamine addition, in high to moderate yields. The DABCO replacement for N-ethyldiisopropylamine in the reac-
tion of anthracene-1,4-diones 4 led unexpectedly to the corresponding 2-thioxo-2,3-dihydroanthra[2,3-d][1,3]thiazole-4,11-diones
10. The reaction of 3H-spiro[1,3-thiazole-2,1'-cyclohexanes] 1d, 2d with Et3N in chlorobenzene under reflux yielded 2,3,4,5-
tetrahydro-1H-carbazole-6,11-diones 15, 16, i.e., ring contraction and fusion products. A plausible mechanism was proposed for the
formation of the products.
Introduction
The 1,4-naphthoquinone structure is common for various promising ones for furthering clinical applications [1]. Mean-
natural products. It is associated with numerous biological while, in terms of further structural and chemical system modi-
activities, such as enzyme-inhibitory, antifungal, antibacterial, fications, the introduction of other heteroatoms (e.g., sulfur)
anticancer, antiproliferative, antiplatelet, anti-inflammatory, through the heterocyclic ring incorporation to the quinone
antiallergic, and antimalarial ones. Benzoquinones fused with system has been one of the most interesting modifications. In
heterocycles containing nitrogen in position 2 are the most fact, 2-alkylthio-1,4-naphthoquinones were found to show cell-
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growth inhibitory properties [2], and dihydrothienonaphtho- the presence of tertiary amines, a selective synthesis of fused
quinones appeared to be potent antitumour compounds [3].
thiazoles, and some of their chemical transformations.
In searching for agents with better pharmacological properties, Results and Discussion
wider activity range, and low side effects it seemed quite We examined in detail the reaction of 2-[butyl(meth-
promising to incorporate two heteroatoms into the heterocycle yl)amino]naphthoquinone 3a with sulfur monochloride and
attached to the naphthoquinone (e.g., thiazole) core. Despite tertiary amines [N-ethyldiisopropylamine (Hünig’s base) and
continuous interest in 1,4-naphthoquinones fused with hetero- 1,4-diazabicyclooctane (DABCO)]. Treatment of naphtho-
cycles, only a limited number of thiazolonaphthoquinones have quinone 3a with S2Cl2 (9 equiv) and Hünig’s base (5 equiv) in
been known so far, no general approach to their synthesis has THF at 0 °C for 72 h with subsequent heating under reflux for
been proposed, and yields are often low. 3-Methyl-2-thioxo-2,3- 2 h (these reaction conditions had been used in the synthesis of
dihydronaphtho[2,3-d][1,3]thiazole-4,9-dione has been shown 3,8-dichloroindeno-2H-[2,1-b]thiophen-2-one from indenyl-
to possess a fungicidal activity to Pyricularia Oryzae [4,5]. A acetic acid [13]) gave with a high yield (81%) only the chlori-
family of thiazolonaphthoquinones fused on a chain with nated product 7a. No sulfurated heterocycles were detected in
nitrogen heterocycles (pyrrole [6,7], and triazoles [8]) were the reaction mixture. The best (practically quantitative) yield of
found to possess antifungal and antitumor activity toward a chloride 7a was achieved by using a 15-fold S2Cl2 excess
number of species causing fungal diseases and toward Walker (Scheme 2). Reactions of naphthoquinone 3a with S2Cl2 and
256 carcinoma cell lines. The compounds with the thiazoloan- Hünig’s base in other solvents, such as chlorobenzene or aceto-
throquinone structure have not been reported in the literature so nitrile, after 1 h under reflux led to the same chlorinated prod-
far. We were interested in developing a general method for the uct 7a albeit in lower yields (70% and 65%, respectively).
synthesis of naphtho- and anthraquinones from readily avail- Sulfur monochloride is known as a powerful chlorinating agent
able 2-aminonaphtho- and anthroquinones as well as in the for chlorination of aromatic and heteroaromatic compounds
study of their chemical properties and side reactions.
[14,15].
A retrosynthetic analysis of naphtho- and anthraquinones 1 and
2 led us to a conclusion that the most reliable route would be a
reaction of sulfur monochloride with dialkylamino derivatives 3
and 4 (Scheme 1). According to the classification of the syn-
thesis of sulfur-containing heterocycles from organic substrates
and S2Cl2, thiazoles 1 and 2 should be generated from the four-
member group shown in red [9]. In turn, dialkylamino deriva-
tives 3 and 4 with two C–H groups activated for the electro-
philic attack, one in the α-position to the carbonyl group [10,11]
and another located near the nitrogen atom [12], could be
Scheme 2: Reaction of 2-[butyl(methyl)amino]naphthoquinone 3a with
S2Cl2 and Hünig’s base.
prepared from the corresponding naphtho- 5 or anthraquinones In an attempt to increase the sulfurating ability of S2Cl2 the
6.
complex 8 obtained from S2Cl2 and 2 equiv of DABCO [16]
was used. We have recently shown that this complex can
In this paper we report a study of a reaction between dialkyl- convert N-substituted 2-methyl-1H-indoles to [1,2]dithiolo[4,3-
aminonaphtho- and anthraquinones and sulfur monochloride in b]indole-3(4H)-thiones [15].
Scheme 1: Retrosynthetic analysis of 2,3-dihydronaphtho[2,3-d][1,3]thiazole-4,9-diones and 2,3-dihydroanthra[2,3-d][1,3]thiazole-4,11-diones.
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Beilstein J. Org. Chem. 2013, 9, 577–584.
A reaction of naphthoquinone 3a with a fivefold excess of com- ylamino derivative 3c where the N-methyl group reacted exactly
plex 8 in chlorobenzene for 0.5 h at −20 °C with subsequent under the same conditions as with other naphthoquinones 3,
treatment with Et3N and heating at 100 °C for another 0.5 h, led giving 3-methyl-2,3-dihydronaphtho[2,3-d][1,3]thiazole-4,9-
to a blue solid, mp 71–74 °C. Microanalysis and mass spec- dione (1c) in a moderate yield.
trometry data allowed the establishment of its molecular
formula as C15H15NO2S. The 1H NMR spectrum showed the The above conditions were further applied to anthraquinones 4
presence of four aromatic protons (7.05–7.58 ppm), two methyl structurally similar to naphthoquinones 3. Anthraquinonothia-
groups (0.98, 3.40 ppm), two methylene groups (1.48, zoles 2 were isolated after treatment of dialkylamino deriva-
1.87 ppm) and one methyne group (5.14 ppm) linked to the tives 4 with complex 8 and triethylamine in chlorobenzene
methylene group (J = 5.5 Hz). The remaining N-methyl group (Scheme 4).
(3.40 ppm), loss of one cyclohexandione C–H proton, and butyl
CH2 fragment conversion to the methyne group undoubtedly In order to compare the reactivity of anthraquinones 4 and
supported a novel thiazole structure, 1a (Scheme 3). The naphthoquinones 3 we studied a reaction of 4 with a mixture of
13C NMR spectrum confirmed these observations.
S2Cl2 and Hünig’s base in THF. After treatment of
anthraquinone 4a with S2Cl2 (9 equiv) and Hünig’s base
Further on, we extended this reaction to other naphthoquinones (5 equiv) in THF at 0 °C for 72 h with subsequent 2 h heating
3. Fused thiazoles 1 were obtained with yields from moderate to under reflux we isolated, along with the chlorinated product 9a,
high. NMR spectroscopy of thiazoles 1 showed that in all the orange crystals 10a, mp 183–185 °C. Microanalysis and mass-
cases either the primary, secondary or tertiary carbon atom at- spectrometry data allowed the establishment of its molecular
tached to the nitrogen atom was included in the thiazole cycle formula as C19H15NO2S2, suggesting the presence of two sulfur
whereas the N-methyl group remained intact, except for dimeth- atoms inserted into the final product instead of four hydrogen
Scheme 3: Synthesis of 2,3-dihydronaphtho[2,3-d][1,3]thiazole-4,9-diones 1.
Scheme 4: Synthesis of 2,3-dihydroanthra[2,3-d][1,3]thiazole-4,11-diones 2.
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Beilstein J. Org. Chem. 2013, 9, 577–584.
atoms. The 1H NMR spectrum showed that both the at 200 °C for 0.5 h giving 3-methyl-1,3-benzothiazole-2(3H)-
anthraquinone ring and butyl group remained intact whereas thione [17]. We described a similar conversion of the meth-
three protons of the methyl group and one of the quinone ring ylene group to thioketone by the action of sulfur monochloride
disappeared. These observations are in agreement with the thia- in the presence of DABCO [18,19]. A plausible mechanism
zole-2-thione structure 10a (Scheme 5). The 13C NMR spec- includes the addition of complex 8 to the activated methylene
trum confirmed this structure by a characteristic C=S signal at group with formation of S-S-DABCO derivative 12 followed by
189.8 ppm. The reaction was then extended to other elimination of a sulfur atom and an HCl molecule [19].
anthraquinone derivatives 4. Fused anthraquinonothiazole-2-
thiones 10 were isolated in yields ranging from moderate to low We believe that naphtho- (1) and anthraquinonothiazoles (2) are
together with chlorinated products 9 (with higher yields in most generated by the same route. The most plausible mechanism is
cases).
shown in Scheme 7.
To confirm the structure of anthraquinonothiazoles 10 we The key step is assumed to be the insertion of two sulfur atoms
treated thiazole 2c with complex 8 in chlorobenzene at 115 °C of complex 8 between two activated CH groups, the first one
for 3 h. Thione 10c identical to the sample prepared from being adjacent to the carbonyl group of the quinone ring and the
anthraquinone 4 was isolated in moderate yield (67%). Naph- second to the methyl or methyne group attached to the nitrogen
thoquinonothiazole 1c reacted with complex 8 by the same atom with the formation of the six-membered dithiazine ring in
pathway yielding corresponding thiazole-2-thione 11 14, similarly to that proposed for 1,2-dithioles prepared from
(Scheme 6).
isopropylamines [14]. Ultimate sulfur extrusion (cf. reference
[13]) would then give stable and planar products 1 and 2.
To the best of our knowledge, there exists only a single example
of the thiazole conversion to thiazole-2-thione, i.e., heating of However, the S2Cl2 and Hünig’s base combination in THF is
3-methyl-2,3-dihydro-1,3-benzothiazole with elemental sulfur preferable in the case of the cyclization of anthraquinone
Scheme 5: Reaction of N-substituted 2-(methylamino)anthracene-1,4-diones 4 with S2Cl2 and Hünig’s base.
Scheme 6: Synthesis of thiazole-2-thiones 10c and 11 from quinonothiazoles 1c and 2c.
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Beilstein J. Org. Chem. 2013, 9, 577–584.
Scheme 7: A plausible mechanism for the formation of naphtho- and anthraquinonothiazoles.
derivatives 4 of the thiazole ring using the N-methyl group. It is unchanged, while one of the α-methylene groups in the
possible that sulfur in intermediate 13, which contains the cyclohexane ring was transformed to the tertiary sp2 carbon
bulkier Y substituent EtN(iPr)2+ compared to DABCO, attacks atom. All data are in agreement with the structure of
the less bulky methyl group giving thiazoles, which are subse- 5-methyl-2,3,4,5-tetrahydro-1H-benzo[b]carbazole-6,11-dione
quently transformed to thiazole-2-thiones 10 by the further (15) [20].
action of S2Cl2 and Hünig’s base.
Anthraquinonothiazole 2d reacted with triethylamine in the
Further study of the reaction between 2-[cyclohexyl(meth- same way as naphthoquinone 1d giving fused pyrrole 16 with
yl)amino]naphthoquinone 1d and complex 8 in chlorobenzene the same yield. The most plausible pathway for this reaction is
allowed us to identify the stable byproduct 15 whose quantity given in Scheme 9.
increased by prolonged heating of the reaction mixture, whereas
the quantity of thiazole 1d decreased. This was assumed to be a The key steps are assumed to be the thiazole ring opening with
thermal conversion of 1d to 15. Base (e.g., triethylamine) was the formation of thiol 17 followed by the dihydropyrrole ring
found to catalyze this reaction and compound 15 was isolated closure under the impact of both quinone and amine groups and
by the heating of 1d in chlorobenzene at 120 °C for 12 h in 78% the generation of the aromatic pyrrole cycle with hydrogen
yield (Scheme 8). According to mass spectrometry and sulfide extrusion by the action of base (triethylamine).
elemental analysis, this is formally a product of H2S elimina- Although, to the best of our knowledge, the transformation of
tion, which was confirmed by isolation of triethylammonium 3H-spiro(thiazol-2,1'-cyclohexanes) to tetrahydroindoles has
hydrogen sulfide in practically quantitative yield from the reac- been so far unknown, similar dehydration of spirooxazolocyclo-
tion mixture. The 1H and 13C spectra showed that the hexane to tetrahydroindoles by treatment with base has been
unchanged naphthoquinone cycle and N-methyl group are previously described [21,22].
Scheme 8: Synthesis of 5-methyl-2,3,4,5-tetrahydro-1H-benzo[b]carbazole-6,11-dione (15) and 5-methyl-2,3,4,5-tetrahydro-1H-naphtho[2,3-
b]carbazole-6,13-dione (16).
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Beilstein J. Org. Chem. 2013, 9, 577–584.
Scheme 9: A plausible mechanism for the conversion of spiro compounds 1d or 2d into carbazolediones 15 and 16.
Conclusion
General procedure for the synthesis of 3-methyl-2,3-dihy-
The reaction of N-substituted 2-(methylamino)naphtho- dronaphtho[2,3-d][1,3]thiazole-4,9-diones 1 and 3-methyl-
quinones and -anthracene-1,4-diones with S2Cl2 provides a 2,3-dihydroanthra[2,3-d][1,3]thiazole-4,11-diones 2: Sulfur
short and convenient route to 2,3-dihydronaphtho[2,3- monochloride (0.40 mL, 5.00 mmol) was added dropwise to a
d][1,3]thiazole-4,9-diones and 2,3-dihydroanthra[2,3- stirred solution of 1,4-diazabicyclooctane (1.12 g, 10.00 mmol)
d][1,3]thiazole-4,11-diones, which are of special interest as bio- in chlorobenzene (80 mL) at −30 °C. The reaction mixture was
logically active compounds. A striking difference in the influ- stirred for 1 h at room temperature, and a solution of the appro-
ence of 1,4-diazabicyclooctane and N-ethyldiisopropylamine in priate 2-(dialkylamino)naphthoquinone 3 or 2-(dialkyl-
the reaction of 2-(methylamino)anthracene-1,4-diones with amino)anthracene-1,4-dione 4 (1.00 mmol) in chlorobenzene
sulfur monochloride was discovered and explained. (40 mL) was added at −30 °C. The reaction mixture was stirred
3H-Spiro(thiazol-2,1'-cyclohexanes) underwent a new ring for 0.5 h at −20 °C, and triethylamine (1.4 mL, 10 mmol) was
contraction and fusion reaction resulting in the formation of added at this temperature. The reaction mixture was stirred for
tetrahydroindoles.
0.5 h at 100 °C and filtered, the solvent was evaporated under
reduced pressure, and the residue was separated by column
chromatography (Silica gel Merck 60 pretreated with triethyl-
Experimental
Melting points were determined on a Kofler hot-stage appa- amine, hexane to hexane/CH2Cl2 mixtures).
ratus and are uncorrected. IR spectra were recorded on a
Specord M-80 instrument in KBr pellets. 1H NMR were General procedure for the reaction of 2-(dialkyl-
recorded on a Bruker WM 250 spectrometer (250 MHz), and amino)anthracene-1,4-diones 4, sulfur monochloride and
13C NMR spectra were recorded on a Bruker AM 300 (75.5 Hünig’s base: Sulfur monochloride (0.72 mL, 9.00 mmol) was
MHz) in CDCl3 solution. J-values are given in hertz (Hz). Mass added dropwise to a stirred solution of the appropriate
spectra were recorded on a Finnigan MAT INCOS 50 instru- 2-(dialkyl-amino)anthracene-1,4-dione 4 (1.00 mmol) and
ment by using electron impact ionization. High-resolution mass N-ethyldiisopropylamine (0.86 mL, 5.00 mmol) in tetrahydrofu-
spectra (HRMS) were measured on a Bruker micrOTOF II rane (65 mL) under argon at −30 °C. The reaction mixture was
instrument by using electrospray ionization (ESI) [23]. The stirred for 1 h at room temperature and then heated under reflux
measurements were done in a positive-ion mode (interface for 2 h and filtered, the solvent was evaporated under reduced
capillary voltage – 4500 V) or in a negative-ion mode (3200 V); pressure, and the residue was separated by column chromatog-
mass range from m/z 50 to 3000 Da; external or internal cali- raphy (Silica gel Merck 60, hexane to hexane/CH2Cl2
bration was done with Electrospray Calibrant Solution (Fluka). mixtures).
A syringe injection was used for solutions in acetonitrile,
methanol or water (flow rate 3 μL/min). Nitrogen was applied General procedure for the synthesis of 3-methyl-2-thioxo-
as dry gas; the interface temperature was set at 180 °C. 2-(Di- 2,3-dihydronaphtho[2,3-d][1,3]thiazole-4,9-dione (11) and
alkylamino)naphthoquinones 3 were prepared as described [24]. 3-methyl-2-thioxo-2,3-dihydroanthra[2,3-d][1,3]thiazole-
2-(Dialkylamino)anthracene-1,4-diones 4 were prepared from 4,11-dione (10с) from 3-methyl-2,3-dihydronaphtho[2,3-
anthracene-1,4-dione by a similar procedure [25].
d][1,3]thiazole-4,9-dione 1c and 3-methyl-2,3-dihydroan-
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Beilstein J. Org. Chem. 2013, 9, 577–584.
5. Yoshida, K.; Kenji, N.; Tetsuda, T.; Suganuma, H.
thra[2,3-d][1,3]thiazole-4,11-dione (2c): Sulfur monochloride
(0.40 mL, 5.00 mmol) was added dropwise to a stirred solution
of 1,4-diazabicyclooctane (1.12 g, 10.00 mmol) in chloroben-
zene (80 mL) at −30 °C. The reaction mixture was stirred for
1 h at room temperature, and a solution of the appropriate
quinonothiazole 1c or 2c (1.00 mmol) in chlorobenzene
(40 mL) was added at −30 °C. The reaction mixture was stirred
for 0.5 h at −20 °C, and triethylamine (1.4 mL, 10 mmol) was
added at this temperature. The reaction mixture was stirred for
0.5 h at 115 °C and filtered, the solvent was evaporated under
reduced pressure, and the residue was separated by column
chromatography (Silica gel Merck 60 pretreated with triethyl-
amine, hexane to hexane/CH2Cl2 mixtures).
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Supporting Information File 1
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Acknowledgments
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We gratefully acknowledge the financial support from the
Russian Foundation for Basic Research (Grant No. 05-03-
32032-a) and from the Presidium of the Russian Academy of
Sciences (Programme No. 8). High-resolution mass spectra
were recorded in the Department of Structural Studies of
Zelinsky Institute of Organic Chemistry, Moscow. We also
thank Professor F. S. Sirovski for helpful discussions.
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