Syntheses of biodynamic heterocycles: baker’s yeast-assisted cyclocondensations of organic nucleophiles and phenacyl chlorides

Article abstract of DOI:10.1007/s11164-017-2880-0

Substituted phenacyl chlorides (1a–f) were cyclocondensed with nucleophiles thiourea (2a) and thiobenzamide (2b) in presence of baker’s yeast (Saccharomyces cerevisiae) as whole-cell enzyme source in acetonitrile at room temperature to obtain 4-(4-substituted phenyl)thiazol-2-amines (3a–f) and 4-(substituted phenyl)-2-phenylthiazoles (4a–f), respectively. Moreover, substituted phenacyl chlorides also reacted with nucleophiles 2-amino-1,3,4-thiadiazole (2c), o-phenylenediamine (2d), 1-amino-2-mercapto-5-phenyl triazole (2e), and pyridin-2-amine (2f) at room temperature in presence of baker’s yeast to give fused heterocycles 6-(4-substituted phenyl)-2-phenylimidazo[2,1-b][1,3,4]thiadiazoles (5a–f), 2-(4-substituted phenyl)quinoxalines (6a–f), 6-(4-substituted phenyl)-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (7a–f), and 2-(4-substituted phenyl)H-imidazo[1,2-a]pyridines (8a–f), respectively. The experimental conditions for these cyclocondensations were optimized to obtain the biodynamic heterocycles in high yield. The unique features of this work are use of baker’s yeast as a cheap and readily available natural source of biocatalyst, noticeable rate acceleration, convenient route to products, cost effectiveness, and scalability.

Full text of DOI:10.1007/s11164-017-2880-0

Res Chem Intermed
DOI 10.1007/s11164-017-2880-0
Syntheses of biodynamic heterocycles: baker’s
yeast-assisted cyclocondensations of organic
nucleophiles and phenacyl chlorides
Lalit D. Khillare1 Umesh R. Pratap1
•
•
Manisha R. Bhosle1 Sambhaji T. Dhumal1
Mahendra B. Bhalerao1 Ramrao A. Mane1
•
•
•
Received: 27 November 2016 / Accepted: 27 January 2017
Ó Springer Science+Business Media Dordrecht 2017
Abstract Substituted phenacyl chlorides (1a–f) were cyclocondensed with nucle-
ophiles thiourea (2a) and thiobenzamide (2b) in presence of baker’s yeast (Sac-
charomyces cerevisiae) as whole-cell enzyme source in acetonitrile at room
temperature to obtain 4-(4-substituted phenyl)thiazol-2-amines (3a–f) and 4-(sub-
stituted phenyl)-2-phenylthiazoles (4a–f), respectively. Moreover, substituted phe-
nacyl chlorides also reacted with nucleophiles 2-amino-1,3,4-thiadiazole (2c), o-
phenylenediamine (2d), 1-amino-2-mercapto-5-phenyl triazole (2e), and pyridin-2-
amine (2f) at room temperature in presence of baker’s yeast to give fused hetero-
cycles 6-(4-substituted phenyl)-2-phenylimidazo[2,1-b][1,3,4]thiadiazoles (5a–f),
2-(4-substituted phenyl)quinoxalines (6a–f), 6-(4-substituted phenyl)-3-phenyl-7H-
[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (7a–f), and 2-(4-substituted phenyl)H-imi-
dazo[1,2-a]pyridines (8a–f), respectively. The experimental conditions for these
cyclocondensations were optimized to obtain the biodynamic heterocycles in high
yield. The unique features of this work are use of baker’s yeast as a cheap and
readily available natural source of biocatalyst, noticeable rate acceleration, conve-
nient route to products, cost effectiveness, and scalability.
Keywords Baker’s yeast Á Cyclocondensations Á Heterocycles
Electronic supplementary material The online version of this article (doi:10.1007/s11164-017-2880-0)
contains supplementary material, which is available to authorized users.
&
Ramrao A. Mane
manera2011@gmail.com
1
Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad,
MS 431 004, India
123

L. D. Khillare et al.
Introduction
At least 50 % of biologically active compounds have a heterocyclic skeleton [1, 2].
Among these, sulfur- and nitrogen-containing heterocyclic compounds have
attracted interest from researchers, and their unique structures have led to several
applications in different pharmaceuticals and biological processes [3]. In view of
this, great efforts are being invested in development of novel synthetic protocols to
facilitate construction of heterocycles [4, 5].
Five- and six-membered heterocycles with two heteroatoms, viz. sulfur and
nitrogen, have been well explored for use as medicaments [4]. Specifically, fused
heterocyclic scaffolds such as quinoxaline are systematically used to generate
therapeutics. Imidazo[2,1-b]thiadiazoles, triazolothiadiazines, and 2-aryl imi-
dazo[1,2-a]pyridines have received considerable attention in the field of drug
discovery due to their interesting biological activities, viz. antioxidant, antidiabetic,
antimitotic, antimicrobial, antivascular, antitumor, anticancer, antipsychotic, and
anticonvulsant actions [6–14]. Clinically used medicaments with S and N
heterocyclic pharmacophores are presented in Fig. 1.
In view of their broad spectrum of pharmacological activities, great interest has
been paid to improvement of protocols for synthesis of thiazoles, quinoxalines,
imidazo[2,1-b][1,3,4]thiadiazoles, triazolothiadiazines, and 2-aryl imidazo[1,2-
a]pyridines [15–27]. The classical/frequently used methods for these heterocycles
O
S
N
NH
O
N
S
O
O
O
N
S
N
HO
Zolimidine(Antiulcer drug)
Meloxicam (Antiinflammatory)
MeO
OMe
S
COOH
MeO
O
N
N
N
H
N
OMe
N
S
N
N
COOH
N
PDE4 Inhibitor
Quinacillin (Penicillin sensitive)
S
N
N
Anthelmintic
Fig. 1 Biologically active compounds containing heterocycle or fused heterocycle ring as core structure
123

Syntheses of biodynamic heterocycles: baker’s yeast…
need a-haloketones as key starting materials [28]. In many cases, such classical
syntheses provide reliable access to heterocyclic compounds, but they are unaccept-
able in not meeting current environmental and safety standards and run under harsh
reaction conditions such as high reaction temperature or presence of strong bases or
acids [29–41]. Thus, more convenient, high-yielding, and ecofriendly synthetic
protocols are always in demand to enable timely supply of a library of heterocyclic
compounds of biological interest to enrich the medicinal chemist’s toolbox.
Considering economic and ecological issues, chemical researchers are paying
more attention to development of new, sustainable processes [42–45] for production
of value-added organics. Use of biocatalysts is increasing and is replacing
conventional catalysts used for organic transformations to obtain value-added
products [46]. The most important advantages of biocatalysts are high selectivity,
reusability, and simpler reaction conditions. Biocatalysts have high selectivity,
which is very desirable in chemical synthesis, as it may offer several benefits such
as avoidance of protection steps, minimization of side reactions, and facilitated
separation [47–49].
Baker’s yeast is easily available and cheap, and has the ability to accelerate
transformations under mild reaction conditions. Applications of baker’s yeast as a
biocatalyst in organic synthesis to catalyze various organic transformations are well
documented [50]. As a whole-cell enzyme source, baker’s yeast (Saccharomyces
cerevisiae) was recently explored and used for generation of value-added
biodynamic heterocycles [51, 52].
There are a few reports of cyclocondensations using biocatalysts. Lipases and
baker’s yeast were recently shown to be able to catalyze cyclocondensations leading
to bioactive heterocycles. However, the role of biocatalysts for rapid construction of
thiazoles, quinoxalines, imidazo[2,1-b][1,3,4]thiadiazoles, triazolothiadiazines, and
imidazo[1,2-a]pyridines has not been investigated. In view of the useful applica-
tions of these heterocycles and in continuation of our earlier interest in biocatalyzed
cyclocondensations [53–55] leading to biodynamic heterocycles, we thought it
worthwhile to use baker’s yeast as a biocatalyst to accelerate cyclocondensations
leading to biodynamic and fused heterocycles.
In this work we attempted cyclocondensations of phenacyl chlorides with various
nucleophiles to obtain 4-(4-substituted phenyl)thiazol-2-amines (3a–f), 4-(substi-
tuted phenyl)-2-phenylthiazoles (4a–f), 6-(4-substituted phenyl)-2-phenylimi-
dazo[2,1-b][1,3,4]thiadiazoles (5a–f), 2-(4-substituted phenyl)quinoxalines (6a–f),
6-(4-substituted phenyl)-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (7a–
f), and 2-(4-substituted phenyl)H-imidazo[1,2-a]pyridines (8a–f), employing
baker’s yeast as a whole-cell source of biocatalysts at ambient temperature in
organic medium (acetonitrile).
Results and discussion
Substituted phenacyl chlorides were condensed with various nucleophiles, namely
thiourea (2a), thiobenzamide (2b), 2-amino-1,3,4-thiadiazole (2c), o-phenylenedi-
amine (2d), 1-amino-2-mercapto-5-phenyl triazole (2e), and pyridin-2-amine (2f) in
123

L. D. Khillare et al.
acetonitrile in presence of activated baker’s yeast at rt to obtain 4-(4-substituted
phenyl)thiazol-2-amines (3a–f), 4-(substituted phenyl)-2-phenylthiazoles (4a–f),
6-(4-substituted phenyl)-2-phenylimidazo[2,1-b][1,3,4]thiadiazoles (5a–f), 2-(4-
substituted phenyl)quinoxalines (6a–f), 6-(4-substituted phenyl)-3-phenyl-7H-
[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (7a–f), and 2-(4-substituted phenyl)H-imi-
dazo[1,2-a]pyridines (8a–f), respectively (Scheme 1).
To determine efficient and convenient reaction conditions for the different
cyclocondensations, we used one-pot cyclocondensation of phenacyl chloride (1a)
and thiourea (2a) as a model reaction in organic medium in presence of activated
baker’s yeast at room temperature to obtain 3a. The model reaction was performed
under identical conditions in different organic solvents, revealing that acetonitrile
was the best solvent not only for 3a but also for compounds 4a, 5a, 6a, 7a, and 8a
(Scheme 1, Fig. 2).
To optimize the quantity of baker’s yeast required to run the model cyclocon-
densation, we attempted the cyclocondensation in acetonitrile with varying amounts
of baker’s yeast from 0.500 g to 3 g using phenacyl chloride (1a) (6 mmol) and
thiourea (2a) (6 mmol). It was observed that high yield of 4-phenylthiazol-2-amine
N
R
N
(8a-f)
S
N
N
N
N
18h rt
R
N
(2f)
NH2
N
N
NH2
(2e)
Ph
N
SH
(7a-f)
R
S
N
S
Ph
22h rt
NH2
H2N
(2a)
NH2
4h rt
(3a-f)
O
Cl
R
(1a-f)
S
Ph
NH2
18h rt
(2b)
NH2
NH2
R
R
N
S
4h rt
N
NH2
N
N
S
18h rt
Ph
(2d)
Ph
(2c)
N
(6a-f)
(4a-f)
R
N
N
N
S
Ph
(5a-f)
Scheme 1 Cyclocondensation of various nucleophiles with phenacyl chlorides. Reaction conditions:
phenacyl chloride (1a–f) (6 mmol), nucleophile (2a–f) (6 mmol), baker’s yeast (2 g) in acetonitrile
(25–30 mL) stirred at room temperature (25 °C)
123

Syntheses of biodynamic heterocycles: baker’s yeast…
(3a) was obtained when the model reaction was performed in presence of 2 g
activated baker’s yeast with 6 mmol initial concentration of each reactant (Table 1).
To investigate the role of baker’s yeast as a catalyst, we ran the model
cyclocondensation under the optimized conditions, i.e., in acetonitrile at room
temperature, in absence of baker’s yeast and noticed that the reaction did not
proceed even when constantly stirring the reaction mass at room temperature for
48 h. This clearly indicates that baker’s yeast plays a catalytic role in accelerating
the rate of cyclocondensation.
Similarly, we ran the cyclocondensations of the phenacyl chlorides with the
above-mentioned different nucleophilic reagents under the above optimized
conditions, i.e., one-pot cyclocondensation in acetonitrile at room temperature in
presence of 2 g baker’s yeast with 6 mmol initial concentration of each
corresponding reactant (Scheme 1) (Table 1, entries 1–6).
After completion of the cyclocondensation under investigation, the reaction mass
was filtered and the residue washed with acetonitrile; the product was isolated from
the solution by removing acetonitrile. The residual yeast mass was discarded as
biodegradable waste.
Inspired by these observations and to generalize the synthetic procedures, a
variety of electronically divergent para-substituted phenacyl chlorides were treated
separately with the nucleophiles at room temperature in presence of acetonitrile.
The physical data along with EcoScale and E-factor results are presented in Table 2.
para-Substituted phenacyl chlorides with several functionalities such as CH3,
OCH3, F, Cl, and Br were utilized under the optimized reaction conditions.
Phenacyl chloride with no substituent on phenyl ring reacted smoothly with
products obtained in excellent yields ranging from 83 to 90 % (Table 2, compounds
3a, 4a, 5a, 6a, 7a, 8a). Electron-donating group such as OCH3 and CH3 present in
the phenacyl chlorides afforded moderate yields of products (Table 2, compounds
100
90
80
70
60
50
40
30
20
10
0
Methanol
Ethanol
Acetonitrile
THF
DCM
3a
4a
5a
6a
7a
8a
Compound
Fig. 2 Screening of solvents. Reaction conditions: phenacyl chloride (1a) (6 mmol), nucleophile (2a–
f) (6 mmol), baker’s yeast (2 g) in solvent (25–30 mL) stirred at room temperature (25 °C). aIsolated
yield
123

L. D. Khillare et al.
Table 1 Effect of different concentrations of baker’s yeast (biocatalyst) on cyclocondensationsa
Entry
Amount of baker’s yeast
Compound (% yieldb)
3a
4a
5a
6a
7a
8a
1
2
3
4
5
6
a
0.500 g
1 g
72
78
85
90
90
90
70
75
85
92
91
91
60
68
81
82
82
80
61
70
82
85
84
83
65
70
86
88
87
86
60
64
75
83
83
82
1.5 g
2 g
2.5 g
3 g
Reaction conditions: phenacyl chloride (1a) (6 mmol), nucleophile (2a–f) (6 mmol), in acetonitrile (25-
30 mL) stirred at room temperature (25 °C) (Scheme 1)
b
Isolated yield
3b, c, 4b, c, 5b, c, 6b, c, 7b, c, 8b, c). Presence of F, Cl, and Br group in the
phenacyl chlorides showed moderate effect on the yield of the cyclocondensations
(Table 2, compounds 3d–f, 4d–f, 5d–f, 6d–f, 7d–f, 8d–f). The products isolated in
this study were characterized by spectral analysis, and their M.P.s were found to be
in good agreement with those reported in literature.
1
All synthesized compounds were characterized using their H NMR (nuclear
magnetic resonance) and 13C NMR and mass spectral data (Electronic Supplemen-
tary Material). The 1H NMR spectrum of compound 3a displays a sharp singlet at d
6.70 ppm for one hydrogen, corresponding to thiazole ring system. Three
characteristic carbon signals were observed at d 102.9, 151.1, and 167.7 ppm in
the 13C NMR spectrum of 3a, belonging to 2-amino thiazole heterocyclic ring
system. The mass spectrum further strengthened the assigned structure of
4-phenylthiazol-2-amine, as it displays an [M ? H]? ion peak at m/z 177.1 for
molecular formula C9H8N2S. Compound 4e shows three characteristic carbon
signals at d 113.0, 155.2, and 168.3 ppm in 13C NMR. Additionally, the mass
spectrum of compound 4e displays an [M ? H]? ion peak at m/z 272.2 for
molecular formula C15H10ClNS, indicating formation of thiazole heterocycle ring.
The mass spectrum of fused heterocycle compound 2,6-diphenylimidazo[2,1-
b][1,3,4]thiadiazole (5a) showed an [M ? H]? ion peak at m/z 278.9 for molecular
formula C16H11N3S. The 1H NMR spectrum of compound 6a displays one hydrogen
singlet at d 9.33 ppm, which supports formation of quinoxaline heterocyclic ring
system. Moreover, the mass spectrum of compound 6a has an [M ? H]? ion peak at
m/z 207.0 for molecular formula C14H10N2S, indicating formation of
2-phenylquinoxaline, a fused heterocycle. Compound 7e shows mass peak, i.e.,
[M ? H]? ion peak at m/z 327.2, for molecular formula C16H11ClN4S. Besides, the
1H NMR spectrum shows a singlet for two hydrogens at d 3.90 ppm, indicating
cyclocondensation resulting in fused [1,2,4]triazolo[3,4-b][1,3,4]thiadiazine.
Most importantly, the characteristic 13C NMR peak at d 108.3 ppm for
compound 8a shows regioselective formation of 2-phenylH-imidazo[1,2-a]pyridine
(Fig. 3).
123

Syntheses of biodynamic heterocycles: baker’s yeast…
Table 2 Baker’s yeast-catalyzed synthesis of heterocycles/fused heterocycles in acetonitrilea
Entry
Compound
R
Yield (%)a
(reaction time)
M.P. (°C)*
EcoScaleb
E-factorb
1
3a
3b
3c
3d
3e
3f
H
90 (4 h)
83 (4 h)
85 (4 h)
85 (4 h)
88 (4 h)
85 (4 h)
88 (4 h)
80 (4 h)
82 (4 h)
88 (4 h)
92 (4 h)
85 (4 h)
82 (18 h)
75 (18 h)
78 (18 h)
78 (18 h)
80 (18 h)
76 (18 h)
85 (18 h)
76 (18 h)
78 (18 h)
80 (18 h)
82 (18 h)
80 (18 h)
88 (22 h)
80 (22 h)
80 (22 h)
85 (22 h)
88 (22 h)
86 (22 h)
83 (18 h)
75 (18 h)
75 (18 h)
78 (18 h)
80 (18 h)
75 (18 h)
148–150
200–203
130–133
189–191
202–204
229–231
90–91
88
21.32
25.5
2
4-OCH3
4-CH3
4-F
84.5
85.5
85.5
87
3
23.42
23.67
24.96
24.90
16.71
19.2
4
5
4-Cl
4-Br
H
6
85.5
87
7
4a
4b
4c
4d
4e
4f
8
4-OCH3
4-CH3
4-F
126–127
115–117
125–127
130–132
122–124
205–207
178–180
140–142
152–154
154–156
220–222
75–77
83
9
84
18.49
17.38
16.79
19.46
17.07
20.30
23.08
18.39
16.52
20.99
19.35
22.82
21.52
23.50
21.85
21.25
13.13
18.24
17.38
14.51
14.68
19.31
21.01
24.50
24.01
24.69
22.92
25.71
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
87
4-Cl
4-Br
H
89
85.5
84
5a
5b
5c
5d
5e
5f
4-OCH3
4-CH3
4-F
80.5
82
82
4-Cl
4-Br
H
83
81
6a
6b
6c
6d
6e
6f
85.5
81
4-OCH3
4-CH3
4-F
99–101
90–91
82
118–120
136–137
131–133
135–137
149–151
156–158
167–169
190–192
213–215
135–137
131–133
144–145
163–165
201–202
215–217
83
4-Cl
4-Br
H
84
83
7a
7b
7c
7d
7e
7f
87
4-OCH3
4-CH3
4-F
83
83
85.5
87
4-Cl
4-Br
H
86
8a
8b
8c
8d
8e
8f
84.5
80.5
80.5
82
4-OCH3
4-CH3
4-F
4-Cl
4-Br
83
80.5
Reaction conditions: phenacyl chloride (1a–f) (6 mmol), nucleophile (2a–f) (6 mmol), baker’s yeast (2 g)
in acetonitrile (25–30 mL) stirred at room temperature (25 °C)
a
Isolated yields. *The melting points of these products prepared in this work are in good agreement with
those reported in literature [58–62]
b
See Electronic Supplementary Material
123

L. D. Khillare et al.
Baker’s yeast is a known source of various enzymes. On disruption of baker’s
yeast, various enzymes are found to be available, displaying specific catalytic
behaviors [53–55, 63]. It is reported that baker’s yeast (Saccharomyces cerevisiae)
is a known source of enzymes such as oxidoreductase and lipases [53–55]. There are
reports that Saccharomyces cerevisiae produces lipases, particularly lipase A
[64, 65] containing the special catalytic triad serine, aspartate, and histidine. This
catalytic triad might be responsible for accelerating the rates of cyclocondensation
in this work. A particular plausible mechanism as a representative case of
cyclocondensation of phenacyl chloride and thiourea leading to 2-amino thiazole is
depicted in Scheme 2.
Experimental
The chemicals used were of laboratory grade. Melting points of all synthesized
1
compounds were determined in open capillary tubes and are uncorrected. H NMR
spectra were recorded on a Bruker DRX-400 MHz NMR spectrometer, and 13C
NMR spectra were recorded on a Bruker DRX-75 NMR in CDCl3/dimethyl
sulfoxide (DMSO)-d6 using tetramethylsilane (TMS) as internal standard; chemical
shifts are reported in d ppm. Direct analysis in real time (DART) mass spectra were
recorded on a Vokudelna ES ? 2000. Reaction progress of each compound was
checked by thin-layer chromatography (TLC) using silica gel, 60F254 aluminum
sheets as adsorbent, with visualisation accomplished by iodine/ultraviolet light.
Baker’s yeast was purchased from local market.
N
N
N
Literature
or
R
N
(I)
(II)
O
Cl
R
N
NH2
R
N
R
This work
N
(II)
N
13C NMR δ 108.3 ppm
N
(8a)
Fig. 3 Regioselectivity of 2-(4-substituted phenyl)H-imidazo[1,2-a]pyridines [56, 57]
123

Syntheses of biodynamic heterocycles: baker’s yeast…
Histidine
Histidine
H
S
N
H
N
O
O
N
N
Cl
NH2
S
N
H
N
H
H
O
H2N
O
O
O
Aspartic anion
Aspartic anion
Histidine
N
N
H
N
N
S
HO
NH2
-H2O
NH2
S
H
O
O
Aspartic anion
Scheme 2 Plausible reaction mechanism for formation of 4-(4-substituted phenyl)thiazol-2-amines (3a–f)
Conclusions
For the first time, various one-pot cyclocondensations have been performed at room
temperature in acetonitrile using activated baker’s yeast (Saccharomyces cerevisiae)
as a safer whole-cell biocatalyst to obtain biodynamic heterocycles, namely 4-(4-
substituted phenyl)thiazol-2-amines (3a–f), 4-(substituted phenyl)-2-phenylthia-
zoles (4a–f), 6-(4-substituted phenyl)-2-phenylimidazo[2,1-b][1,3,4]thiadiazoles
(5a–f), 2-(4-substituted phenyl)quinoxalines (6a–f), 6-(4-substituted phenyl)-3-
phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (7a–f), and 2-(4-substituted
phenyl)H-imidazo[1,2-a]pyridines (8a–f) in better to excellent yield. The developed
protocols are convenient, cost effective, and scalable, and follow certain green
principles.
Acknowledgements The authors are grateful to Professor D. B. Ingle for invaluable discussion and
guidance. The authors are very grateful to CDRI, Lucknow for providing spectral facilities. L.D.K. is also
grateful to U.G.C., New Delhi, India for financial assistance in the form of a UGC-NET Senior Research
Fellowship.
123

L. D. Khillare et al.
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