A facile and rapid method for preparation of thiazine and thiadiazine derivatives by sonication technique

Article abstract of DOI:10.1080/10426500902773328

Ultrasound accelerated synthesis of 2,3-(substituted)benzo-1,4-thiazino[5, 6-b]-4H-9H-7- methyl-10-oxoquinolines (4), 7-substituted-2,2-dimethyl-2,3- dihydro-1H,10H-phenothiazin- 4-one (5), 4-substituted-3,9, 10-trihydro-11-oxo- quinolino[2,3-b]-1,3,4-thiadiazino[2,3-d]- 1,2,4-triazole (6), and 7,7-dimethyl-7,8-dihydro-3H,5H,6H-1,2,4-triazolo[3,4-b][1,3,4] benzothiadiazin-9-one (7) from carbostyril and dimedone using sulfur powder and iodine as a catalyst in THF is reported. The structures of the compounds have been elucidated on the basis of spectral and elemental analysis.

Full text of DOI:10.1080/10426500902773328

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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A Facile and Rapid Method for
Preparation of Thiazine and Thiadiazine
Derivatives by Sonication Technique
Vijay V. Dabholkar a & Faisal Y. Ansari a
a Organic Research Laboratory, Department of Chemistry , K.C.
College , Churchgate, Mumbai, India
Published online: 03 Feb 2010.
To cite this article: Vijay V. Dabholkar & Faisal Y. Ansari (2010) A Facile and Rapid Method for
Preparation of Thiazine and Thiadiazine Derivatives by Sonication Technique, Phosphorus, Sulfur, and
Silicon and the Related Elements, 185:2, 298-305
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Phosphorus, Sulfur, and Silicon, 185:298–305, 2010
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500902773328
A FACILE AND RAPID METHOD FOR PREPARATION
OF THIAZINE AND THIADIAZINE DERIVATIVES
BY SONICATION TECHNIQUE
Vijay V. Dabholkar and Faisal Y. Ansari
Organic Research Laboratory, Department of Chemistry, K.C. College,
Churchgate, Mumbai, India
Ultrasound accelerated synthesis of 2,3-(substituted)benzo-1,4-thiazino[5,6-b]-4H-9H-7-
methyl-10-oxoquinolines (4), 7-substituted-2,2-dimethyl-2,3-dihydro-1H,10H-phenothiazin-
4-one (5), 4-substituted-3,9, 10-trihydro-11-oxo-quinolino[2,3-b]-1,3,4-thiadiazino[2,3-d]-
1,2,4-triazole (6), and 7,7-dimethyl-7,8-dihydro-3H,5H,6H-1,2,4-triazolo[3,4-b][1,3,4]
benzothiadiazin-9-one (7) from carbostyril and dimedone using sulfur powder and iodine
as a catalyst in THF is reported. The structures of the compounds have been elucidated on
the basis of spectral and elemental analysis.
Keywords Amino-triazole; aromatic amine; carbostyril; dimedone; sonication; thiadiazine;
thiazine
INTRODUCTION
During the last 10 years, a number of publications and reviews have advocated the
use of ultrasound technology in organic synthesis. Ultrasound in organic synthesis is an
attractive, constantly growing field of organic chemistry. The advantages of ultrasound-
assisted chemical reactions include higher yields, shorter reaction times, and milder reac-
tion conditions when compared with classical methods.1–5 The use of ultrasound irradiation
technique for activating various reactions is well documented in the literature, such as
synthesis of azoles and diazenes,6 Reformatsky reaction,7 oxidation of substrates such as
hydroquinones,8 conversion of nitro compounds to carbamates,9 pinacol coupling,10 and
Ullmann condensation.11 Carbostyril12 and dimedone13 constitute a unique group of com-
pounds due to the simultaneous presence of characteristic features such as a β-diketone
group as a starting material. Thazines are known to exhibit various types of biological activ-
ities such as Ca2+ antagonist; blood platelet aggregation inhibitors;14 and antipsychotic,15
antiviral,16 antimicrobial,17 and antihypertensive18 agents. Similarly, the thiadiazine nucleus
is a versatile pharmacophore, which exhibits a wide variety of biological activity. Many
Received 13 April 2008; accepted 21 January 2009.
The authors are thankful to the Principal Ms. Manju J. Nichani and Management of K.C. College, Churchgate,
Mumbai, India, for constant encouragement and providing necessary facilities. The authors are also thankful to
the Director, Institute of Science, Mumbai, India, for providing spectral analyses.
Address correspondence to Vijay V. Dabholkar, Organic Research Laboratory, Department of Chemistry,
K.C. College, Churchgate, Mumbai 400 020, India. E-mail: vijaydabholkar@gmail.com
298

SONICATION TECHNIQUE FOR THIAZINE DERIVATIVES
299
of its compounds are antimicrobial,19 anti-irradiation,20 and antiparasitic agents.21 Fused
s-triazoles and their derivatives have been investigated for their potential pharmacological
properties such as antifungal,22 antidepressant,23 and plant growth regulators.24
Our research group has a longstanding interest in the synthesis of heterocyclic com-
pounds by newer methods such as microwave25–28 and sonication29–31 aiming to develop
more rapid and advantageous construction of libraries of small heterocyclic compounds.
As a result we have recently reported the synthesis of benzothiazipine, thiophene, triazole,
thiadiazole, and spiro oxadiazole, and also their biological studies.29–31 In view of these
observations, and as an extension of our earlier work, thiazine and thiadiazine derivatives
have been prepared by sonication methods as well as by conventional synthetic methodolo-
gies. The synthesis of novel thiazines and thiadiazine32,33 have been reported by us using
2-bromo dimedone/3-bromo carbostyril with aminothiophenols, and in this article we de-
scribe the synthesis of thiazine/thiadiazine using an alternative route by reacting substituted
amines/amino-triazole using sulfur powder and iodine as a catalyst in the presence of THF
as a solvent.34
However, in the earlier reported processes, expensive chemicals were used and the
method was time consuming. In order to overcome these limitations and in vision of
the requirement of green chemistry for energy saving, high efficiency, and environmen-
tal benevolence, we carried out this series of reactions under sonication, in addition to
R1
NH2
(1 A )
O
H3C
CH3
(a)
H3C
N
H
O
O
O
(3)
(2)
O
O
S
R1
H3C
S
R1
H3C
N
H
N
H
N
H
CH3
(5)
(4)
R1= H, CH3, OCH3, Cl
Sulphur powder,Iodine/THF
Scheme 1
(a) =

300
V. V. DABHOLKAR AND F. Y. ANSARI
conventional methods. It was found that the sonication method is environmentally ben-
eficial and superior to the conventional method. It is also a very rapid method for the
preparation of thiazine and thiadiazine derivatives (Scheme 1).
RESULT AND DISCUSSION
The series of heterocyclic compounds 4, 5, 6, and 7 have been synthesized as depicted
in Schemes 1 and 2. The starting materials carbostyril (2) and dimedone (3) were synthesized
as reported earlier.20 The reaction of 2 and 3 with substituted aromatic amines, sulfur, and
iodine in THF gave the 2,3-(substituted)benzo-1,4-thiazino [5, 6-b]-4H-9H-7-methyl-10-
oxo quinolines 4 and 7-substituted-2, 2-dimethyl-2,3-dihydro-1H,10H-Phenothiazin-4-one
5 (Scheme 1). In the IR spectra of compounds 4, the following characteristic absorption
N
N
N
NH2
(1T )
O
H3C
CH3
(a)
N
O
O
O
H
R1
(2)
(3)
O
O
S
S
N
N
N
N
H3C
N
N
N
H
N
H
N
H
CH3
R1
(7)
(6)
R1 = CH3, OCH3, Cl
Sulphur powder,Iodine/THF
(a) =
Scheme 2

SONICATION TECHNIQUE FOR THIAZINE DERIVATIVES
301
bands were observed: 1687 υmax/cm−1 (C O) and 3425 υmax/cm−1 (NH). In its 1H NMR
spectra, two signals of NH group at 10.25 and 12.50 ppm were observed. Similarly, the
compounds 5 were confirmed by IR spectra, which showed NH bands in the region of 3285
1
υmax/cm−1 and C O absorption bands at 1240 υmax/cm−1. Also, in its H NMR spectra,
the NH group shows a chemical shift that is a characteristic of thiazine. This is observed in
the downfield region at 8.9–9.4 ppm and also supports the proposed structure.
Similarly, the compound 4-substituted-3,9,10-trihydro-11-oxo-quinolino[2,3-b]-
1,3,4-thiadiazino[2,3-d]-1,2,4-triazole (6) and 7,7-dimethyl-7,8-dihydro-3H,5H,6H-1,2,4-
triazolo[3,4-b][1,3,4]benzothiadiazin-9-one (7) have been prepared by the same procedure
using amino-triazole (Scheme 2). Evidence of the formation of compound 6 was shown by
the appearance of a signal at 1632 υmax/cm−1 and 3137 υmax/cm−1 for (C O) and (NH).
In its 1H NMR spectra, two signals of NH group at 12.43 and 12.72 ppm were observed.
Similarly, the compound 7 was confirmed by IR spectra, which showed NH bands in the
region of 3267 υmax/cm−1 and C O absorption bands at 1623 υmax/cm−1. Also, in its 1H
NMR spectrum, the NH group shows a chemical shift that is characteristic of thiadazine.
This was observed in the downfield region at 11.43 ppm, and the CH in the triazole ring
was shown at 7.45 ppm. This also supports the proposed structure.
CONCLUSION
The process of ultrasound irradiation for synthesis of the title compound undergoes a
significant reduction in the reaction time. There is simplicity in the operation, the reaction
is cleaner, the process is easier, and the yield is enhanced. The procedure clearly highlights
the advantages of ultrasound technique. Both synthones (carbostyril and dimedone)
have been successfully utilized in the preparation of 2,3-(substituted)benzo-1,4-thiazino
[5,6-b]-4H-9H-7-methyl-10-oxoquinolines (4), 7-substituted-2,2-dimethyl-2,3-dihydro-
1H,10H-phenothiazin-4-one (5), 4-substituted-3,9,10-trihydro-11-oxo-quinolino[2,3-b]-
1,3,4-thiadiazino[2,3-d]-1,2,4-triazole (6), and 7,7-dimethyl-7,8-dihydro-3H,5H,6H-
1,2,4-triazolo[3,4-b][1,3,4] benzothiadiazin-9-one (7), and their structures were elucidated
with the help of elementary and spectral analysis.
EXPERIMENTAL
The chemicals were supplied by E. Merck (Germany) and S.D. Fine Chemicals
(India). The melting points of synthesized compounds were determined in open capillary
tubes using a Veego VMP-1 melting point apparatus, expressed in ◦C, and are uncorrected.
The purity of the compounds was monitored by thin layer chromatography on silica gel
coated aluminum plates (Merck) as an adsorbent and UV light as a visualizing agent.
IR spectra (KBr in υmax/cm−1) were recorded on a Perkin-Elmer spectrophotometer in
1
the range of 400–4000 υmax/cm−1. H NMR spectra were recorded on Brucker Avance
500 MHz NMR spectrophotometer from International Equipment Trading LTD, using
CDCl3/DMSO-d6 as a solvent and TMS as an internal standard (chemical shifts in δ,
given in ppm). C, H, N estimations were done on Carlo Erba 1108 (C H N) Elemental
Analyser. The experiment under ultrasound irradiation was carried out in probe ultrasound
manufactured by Dakshin pvt Ltd, Mumbai (Electrical Supply 230V A.C., 50 Hz).

302
V. V. DABHOLKAR AND F. Y. ANSARI
2,3-(Substituted)benzo-1,4-thiazino[5,6-b]-4H-9H-7-
methyl-10-oxoquinolines (4)
Method A (ultrasound method): General procedure. The mixture of car-
bostyrils (CAB) (2) (50 mmol), substituted amines (1A) (50 mmol), and sulfur powder
(15.6 mmol) in THF (5 mL) was irradiated on a sonicator in the presence of iodine (1
mmol) as catalyst for 25 min. After completion of the reaction (monitored on TLC) and the
contents were cooled, the solid formed was filtered, washed with dil. HCl and warm water
followed by CS2, and recrystallized from glacial acetic acid.
Method B (conventional method): General procedure. An equimolar mix-
ture of carbostyrils (CAB) (2) (50 mmol), substituted amines (1A) (50 mmol), and sulfur
powder (15.6 mmol) in THF 5 mL was refluxed in the presence of iodine (1 mmol) as cat-
alyst for 3 h at 180◦C. Upon completion of the reaction (monitored by TLC), the mixture
was brought to room temperature, the solid formed was filtered washed with dil. HCl with
followed by CS2, and then recrystallized from glacial acetic acid.
2,3-Benzo-1,4-thiazino[5,6-b]-4H-9H-7-methyl-10-oxoquinolines
(4a).
This compound was obtained in 69% yield (Soni 84%), mp 205◦C; [found: C, 68.45;
H, 4.21; N, 9.92. C16H12ON2S requires C, 68.5; H, 4.28; N, 10.00%]; υmax/cm−1: 1620
(C O), 3248 (NH); δH: 2.4 (s, 3H, CH3), 6.91–8.22 (m, 7H, ArH), 10.98 (s, 1H, ring NH),
12.48 (s, 1H, ring NH).
2,3-(4ꢀ-Methyl)benzo-1,4-thiazino[5,6-b]-4H-9H-7-methyl-10-oxoquino
lines (4b). This compound was obtained in 60% yield (Soni 83%), mp 202◦C; [found: C,
69.32; H, 4.72; N, 9.46. C17H14ON2S requires C, 69.38; H, 4.76; N, 9.52%]; υmax/cm−1
:
1657 (C O), 3264 (NH); δH: 2.27 (s, 3H, CH3), 2.32 (s, 3H, CH3), 3.80 (s, 3H, OCH3),
6.7–8.2 (m, 6H, ArH), 10.85 (s, 1H, ring NH), 12.04 (s, 1H, ring NH).
2,3-(4ꢀ-Methoxy)benzo-1,4-thiazino[5,6-b]-4H-9H-7-methyl-10-oxoquino
lines (4c). This compound was obtained in 64% yield (Soni 80%), mp 204◦C; [found: C,
65.67; H, 4.38; N, 8.92. C17H14O2N2S requires C, 65.80; H, 4.51; N, 9.03%]; υmax/cm−1
:
1657 (C O), 3264 (NH); δH: 2.27 (s, 3H, CH3), 3.80 (s, 3H, OCH3), 6.70–8.20 (m, 6H,
ArH), 10.85 (s, 1H, ring NH), 12.04 (s, 1H, ring NH).
2,3-(4ꢀ -Chloro)benzo-1,4-thiazino[5,6-b]-4H-9H-7-methyl-10-oxoquino
lines (4d). This compound was obtained in 65% yield (Soni 84%), mp 148◦C; [found: C,
60.87; H, 3.42; N, 8.82. C16H11ON2SCl requires C, 60.95; H, 3.49; N, 8.88%]; υmax/cm−1
:
1653 (C O), 3300 (NH); δH: 2.3 (s, 3H, CH3), 7.14–7.72 (m, 6H, ArH), 11.5 (s, 1H, ring
NH), 12.15 (s, 1H, ring NH).
7-Substituted-2,2-dimethyl-2,3-dihydro-1H,10H-Phenothiazin-4-one (5)
Method A (ultrasound method): General procedure. A mixture of dimedone
(DIM) (3) (50 mmol), substituted amines (1A) (50 mmol), sulfur powder (15.6 mmol),
iodine (1 mmol), and THF (5 mL) as a solvent was taken in a 100 mL round bottom flask
and subjected to ultrasound for 15 min. After monitoring the reaction on TLC, the reaction
mixture was cooled at room temperature to obtain 5, which was filtered and washed with
dil. HCl, warm water, and then with CS2. It was recrystallized from ethanol.
Method B (conventional method): General procedure. Mixture of dime-
done (DIM) (3) (50 mmol), substituted amines (1A) (50 mmol), sulfur powder (15.6
mmol), iodine (1 mmol), and THF (5 mL) as a solvent was taken in 100 mL round bottom
flask, and the mixture was heated at 80◦C for 3 h. After monitoring the reaction on TLC,
the reaction mixture was worked up in the same manner as discussed above.

SONICATION TECHNIQUE FOR THIAZINE DERIVATIVES
303
2,2-Dimethyl-2,3-dihydro-1H,10H-phenothiazin-4-one (5a). This com-
pound was obtained in 64% yield (Soni 86%), mp 264◦C; [found: C, 68.23; H, 6.32; N,
5.45. C14H15ONS requires C, 68.57; H, 6.12; N, 5.71%]; υmax/cm−1: 1618 (C O), 3276
(NH); δH: 1.10 (s, 6H, 2CH3), 2.17 (s, 2H, CH3), 2.29 (s, 2H, CH2), 6.22–7.24 (m, 4H,
ArH), 8.96 (s, 1H, ring NH).
7-Methyl-2,2-dimethyl-2,3-dihydro-1H,10H-phenothiazin-4-one
(5b).
This compound was obtained in 59% yield (Soni 88%), mp 194◦C; [found: C, 69.21;
H, 6.68; N, 5.21. C15H17ONS requires C, 69.49; H, 6.56; N, 5.40%]; υmax/cm−1: 1608
(C O), 3262 (NH); δH: 1.08 (s, 6H, 2CH3), 2.2 (s, 2H, CH3), 2.30 (s, 2H, CH2), 2.42
(s, 2H, CH3), 7.05–7.35 (m, 3H, ArH), 9.42 (s, 1H, ring NH).
7-Methoxy-2,2-dimethyl-2,3-dihydro-1H,10H-phenothiazin-4-one (5c).
This compound was obtained in 67% yield (Soni 80%), mp 242◦C; [found: C, 69.23;
H, 6.74; N, 5.21. C15H17O2NS requires C, 69.49; H, 6.59; N, 5.40%]; υmax/cm−1: 1610
(C O), 3312 (NH); δH: 1.08 (s, 6H, 2CH3), 2.08 (s, 2H, CH3), 2.15 (s, 2H, CH2), 3.9
(s, 3H, OCH3), 7.05–7.35 (m, 3H, ArH), 9.34 (s, 1H, ring NH).
7-Chloro-2,2-dimethyl-2,3-dihydro-1H,10H-phenothiazin-4-one
(5d).
This compound was obtained in 62% yield (Soni 84%), mp 215◦C; [found: C, 69.45;
H, 6.48; N, 5.32. C14H14ONSCl requires C, 69.49; H, 6.59; N, 5.40%]; υmax/cm−1: 629
(C Cl), 1610 (C O), 3312 (NH); δH: 1.11 (s, 6H, 2CH3), 2.12 (s, 2H, CH3), 2.24 (s, 2H,
CH2), 7.15–7.65 (m, 3H, ArH), 9.21 (s, 1H, ring NH).
4-Substituted-3,9,10-trihydro-11-oxo-quinolino[2,3-b]-1,3,4-
thiadiazino [2,3-d]–1,2,4-triazole (6a–c)
Method A (ultrasound method): General procedure. An equimolar solution
of carbostyril (CAB) (2) (50 mmol) and triazole (1T) (50 mmol), sulfur powder (15.6
mmol), iodine (1 mmol), and THF (5 mL) as a solvent was taken in 100 mL round bottom
flask and subjected to ultrasound irradiation for 28 min. After monitoring the reaction on
TLC, the reaction mixture was cooled at room temperature to obtain 6, which was filtered
and washed with dil. HCl, warm water, and then with CS2. It was recrystallised from
ethanol.
Method B (conventional method): General procedure. A mixture of car-
bostyril (CAB) (2) (50 mmol), triazole (1T) (50 mmol), sulfur powder (15.6 mmol), iodine
(1 mmol), and THF (5 mL) as a solvent was taken in 100 mL round bottom flask, and the
mixture was heated at 80◦C for 4 h. After monitoring the reaction on TLC, the reaction
mixture was worked up in the same manner as discussed above.
4-Methyl-3,9,10-trihydro-11-oxo-quinolino[2,3-b]-1,3,4-thiadiazino[2,3-
d]-1,2,4-triazole (6a). This compound was obtained in 63% yield (Soni 78%), mp 225◦C
[found: C, 53.05; H, 3.24; N, 25.72 C12H9ON5S requires C, 53.13; H, 3.32; N, 25.8%];
υmax/cm−1: 3137 (NH), 1632 (C O), 1585 (C N). δH: 2.47 (s, H, CH3), 7.18–7.91
(m, 4H, aromatic H& CH), 12.43 (s, ring NH), 12.72 (s, ring NH).
4-Methoxy-3,9,10-trihydro-11-oxo-quinolino[2,3-b]-1,3,4-thiadiazino[2,3-
d]-1,2,4-triazole (6b). This compound was obtained in 57% yield (Soni 82%), mp
254◦C [found: C, 50.17; H, 3.13; N, 24.39. C12H9O2N5S requires C, 50.10; H, 3.04; N,
24.32%]; υmax/cm−1: 3121 (NH), 1611 (C O), 1565 (C N). δH: 3.82 (s, H, OCH3),
7.23–7.87 (m, 4H, aromatic H & CH), 12.41 (s, ring NH), 12.70 (s, ring NH).
4-Chloro-3,9,10-trihydro-11-oxo-quinolino[2,3-b]-1,3,4-thiadiazino[2,3-
d]-1,2,4-triazole (6c). This compound was obtained in 60% yield (Soni 84%), mp

304
V. V. DABHOLKAR AND F. Y. ANSARI
268◦C [found: C, 51.36; H, 2.72; N, 27.23. C11H7ON5SCl requires C, 51.30; H, 2.65; N,
27.15%]; υmax/cm−1: 3130 (NH), 1610 (C O), 1570 (C N), 625 (C Cl). δH: 7.21–7.89
(m, 4H, aromatic H& CH), 12.34 (s, ring NH), 12.70 (s, ring NH).
7,7-Dimethyl-7,8-dihydro-3H,5H,6H-1,2,4-triazolo[3,4-b][1,3,4]
benzothiadiazin-9-one (7)
Method A (ultrasound method): General procedure. An equimolar solution
of dimedone (DIM) (3) (50 mmol), and triazole (1T) (50 mmol), sulfur powder (15.6 mmol),
iodine (1 mmol), and THF (5 mL) as a solvent was taken in 100 mL round bottom flask
and subjected to ultrasound for 22 min. After monitoring the reaction on TLC, the reaction
mixture was cooled at room temperature to obtain 7, which was filtered and washed with
dil. HCl, warm water, and then with CS2. It was recrystallized from ethanol.
Method B (conventional method): General procedure. Mixture of dime-
done (DIM) (3) (50 mmol), triazole (1T) (50 mmol), sulfur powder (15.6 mmol), iodine
(1 mmol), and THF (5 mL) as a solvent was taken in 100 mL round bottom flask and the
mixture was heated at 80◦C for 3.5 h. After monitoring the reaction on TLC, the reaction
mixture was worked up in the same manner as discussed above.
The above compound was obtained in 69% yield (Soni 86%), mp 261◦C; [found: C,
50.76; H, 5.02; N, 23.65 C10H12ON4S requires C, 50.84; H, 5.08; N, 23.72%];υmax/cm−1
:
1632 (C O), 3202 (NH); δH: 0.99 (s, 6H, 2×CH3), 2.31 (s, 2H, CH2), 2.38 (s, 2H, CH2),
7.45 (s, H, N CH), 11.72 (s, 1H, NH)
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