ISSN

0974-4150 (Online)
0974-4169 (Print)


Author(s): Meghmala R. Sangvikar, Gayatri M. Phadnaik, Omprakash S. Chavan

Email(s): omprakashschavan@gmail.com

DOI: 10.52711/0974-4150.2021.00058   

Address: Meghmala R. Sangvikar1, Gayatri M. Phadnaik2, Omprakash S. Chavan1*
1P.G., Department of Chemistry, Badrinarayan Barwale College, Jalna - 431213, Maharashtra, India and Affiliated to Dr. Babasaheb Ambedkar Marathwada University, Aurangabad.
2Department of Chemistry, Institute of Science, Nagpur - 440012, Maharashtra, India and Affiliated to Rashtrasant Tukadoji Maharaj University, Nagpur.
*Corresponding Author

Published In:   Volume - 14,      Issue - 5,     Year - 2021


ABSTRACT:
The kinetics of DMSO (dimethylsulphoxide) assisted one pot cyclocondensation of bisanilino disulphide and 1,3-dicarbonyls has been investigated using spectral method. The kinetic measurements have been carried by varying media, temperature and concentration of the reactants. The assistance of DMSO is investigated. The order of reaction, effects of substituents with dicarbonyls on the rates and thermodynamic parameters has also been reported. First time reaction conditions are optimised for performing the cyclocondensation conveniently and rapidly. Probably mechanism has been proposed and order of reaction was determined on the basis of rate expression and was in agreement with second order rate equation, used for the determination of rate constants.


Cite this article:
Meghmala R. Sangvikar, Gayatri M. Phadnaik, Omprakash S. Chavan. Kinetics and Mechanism of Formation of 2,3-Disubstituted 1,4-Benzothiazines: One Pot DMSO Assisted Cyclocondensation of Bisanilino Disulphide and 1, 3-Dicarbonyls. Asian Journal of Research in Chemistry. 2021; 14(5):339-4. doi: 10.52711/0974-4150.2021.00058

Cite(Electronic):
Meghmala R. Sangvikar, Gayatri M. Phadnaik, Omprakash S. Chavan. Kinetics and Mechanism of Formation of 2,3-Disubstituted 1,4-Benzothiazines: One Pot DMSO Assisted Cyclocondensation of Bisanilino Disulphide and 1, 3-Dicarbonyls. Asian Journal of Research in Chemistry. 2021; 14(5):339-4. doi: 10.52711/0974-4150.2021.00058   Available on: https://ajrconline.org/AbstractView.aspx?PID=2021-14-5-7


REFERENCE:
1    Finguelli R., Milanese L., Schiafella F., Role of 1,4-benzothiazine derivatives in medicinal chemistry. Mini Rev Med Chem. 2005; 5:1061-1673. doi: 10.2174/138955705774933365.
2    Erik De Clercq, Toward Improved Anti-HIV Chemotherapy: Therapeutic Strategies for Intervention with HIV Infections. J. Med. Chem. 1995; 38(14):2491–2517. https://doi.org/10.1021/jm00014a001
3    Shamsuzzaman, Ayaz Mahmood Dar, Hena Khanam, Manzoor Ahmad Gatoo, Anticancer and antimicrobial evaluation of newly synthesized steroidal 5,6 fused benzothiazines. Arabian J. of Chem. 2014; 7:461-468. https://doi.org/10.1016/j.arabjc.2013.06.027.
4    Cecchetti V. C. Tabarrini O. and etal Sabatini S. Filipponi E. Testai, L. Spogli. R. Martinotti E. Fravolini A. Highly Potent 1,4-Benzothiazine Derivatives as KATP-Channel Openers. J. Med. Chem. 2003; 46:3670-3679. https://doi.org/10.1021/jm030791q.
5    Giuliano Grandolini, Luana Perioli, Valeria Ambrogi. Synthesis of some new 1,4-benzothiazine and 1,5-benzothiazepine tricyclic derivatives with structural analogy with TIBO and their screening for anti-HIV activity. Eur. J. Med. Chem. 1999; 34:701-709. https://doi.org/10.1016/S0223-5234(99)00223-8.
6    Dipika Vyawahare, Anna Pratima Nikalje. Efficient One Pot Green Synthesis of 2-Aryl/ Heteryl- Benzothiazoles as Anti-inflammatory Agents. Asian J. Research Chem. 2010; 3(4): 872-875. DOI: 10.5958/0974-4150
7    Tawada, H.; Sugiyama, Y.; Ikeda, H.; Yamakmoto, Y.; Megurok. Studies on Antidiabetic Agents. IX.: A New Aldose Reductase Inhibitor, AD-5467, and Related 1, 4-Benzoxazine and 1, 4-Benzothiazine Derivatives: Synthesis and Biological Activity. Chem. Pharm. Bull. 1990; 38:1238-1245. https://doi.org/10.1248/cpb.38.1238.
8    Violetta Cecchetti, Fausto Schiaffella, Oriana Tabarrini, Arnaldo Fravolini. (1,4-Benzothiazinyloxy) alkylpiperazine derivatives as potential antihypertensive agents. Bioorganic and Medicinal Chemistry Letters. 2000; 10(5):465-468. https://doi.org/10.1016/S0960-894X(00)00016-0.
9    Rathore, B. S.; Kumar, M. Synthesis of 7-chloro-5-trifluoromethyl/7-fluoro/7-trifluoromethyl-4H-1,4-benzothiazines as antimicrobial agents Bioorg. and Med. Chem. 2006; 14:5678-5682. https://doi.org/10.1016/j.bmc.2006.04.009.
10    VA Navale, SS Mokle, Archana Y Vibhute, KG Karamunge, SV Khansole, SB Junne, YB Vibhute. Microwave-Assisted Synthesis and Antibacterial Activity of Some New Flavones and 1, 5-Benzothiazepines.Asian J. Research Chem. 2009; 2(4): 472-475. DOI: 10.5958/0974-4150.
11    Kalekar M. C., Bhat A. R., Koli V. R. Synthesis of 1, 4 Benzothiazine Derivatives for Antimicrobial Activity. Asian J. Research Chem. 4(11): Nov., 2011; Page 1661-1663. DOI: 10.5958/0974-4150.
12    Praveen Kumar Sharma, Reena Makkar and Simranjeet Singh. Antibacterial, Antifungal and Antioxidant activities of substituted 4H-1,4-benzothiazines. Der Pharma Chemica. 2016; 8(11): 156-159.
13    Gupta, R R; Dev, P K; Sharma, M L; Rajorla, C M; Gupta, Archana; Nyatl, M. Anticancer activities of 2,3-dihydro-1,4-benzothiazines, and of their 4-(N-alkyl amides) and 4-(N-alkyl N-nitrosoamides). Anti-Cancer Drugs. 1993; 4(5): 589-592.
14    Praveen Kumar Sharma, Andleeb Amin and M. Kumar, Synthetic Methods of Medicinally Important Heterocycles-thiazines: A Review. Open Med. Chem. J. 2020; 14:71-82. DOI: 10.2174/1874104502014010071
15    Tanaka, R.; Teramura, K.; Yokoyama, S. Chem. Abstr. 1966; 65:9062.
16    Strain, W. H.; Dickey. J., Chem. Abstr. 1946; 40:1889.
17    Gurram, R. M.; Bhuniya, D.; Das, S. K.; Sharam, S.K.; Chakrabarti, R.; Iqbal, J. USPTO patent Application, 2007, 0043035.
18    Maheshwari, M., And A. Goyal. A Review: Synthesis and Medicinal Importance of 1,4-Benzothiazine Analogues. Asian J. Of Pharma. and Clinical Research. 2015; 8(2): 41-46.
19    Gupta, R. R.; Phenothiazines and 1,4‐benzothiazines. Chemical and Biomedical aspects, Elsevier Publication, Amsterdam, 1988.
20    Banerji, K.; Kothari, S. Ind. J. of Chem. 1997; 36B: 1156-1158.
21    Kumbhat, Vinita Sharma, Pradeep K Banerji, Kalyan K., Kinetics and mechanism of oxidation of aliphatic aldehydes by 2, 2' –bipyridinium chlorochromate, Ind. J. of Chem.2000; 39A:1169-1173. http://hdl.handle.net/123456789/21210.
22    M. Shireesha, L. Madhavi, G. Tuljarani. Spectrophotometric Determination of Clopidogrel in Pharmaceutical Formulations. Asian J. Research Chem. 2011; 4(10): 1566-1568. DOI: 10.5958/0974-4150
23    Khorassani, S. M. M.; Maghsoodlu, M. T.; Ebrahimi, A.; Roohi, H.; Zakarianezad, M. UV spectrophotometric study of the kinetics and mechanism of the reactions between triphenylphosphine, dialkyl acetylenedicarboxylates and NH-acid. J. Iranian chem. Soc. 2006; 3:223-232. https://doi.org/10.1007/BF03247212.
24    Burungale, A.S.; Padwal, S.L.; Bondage, S.P; Mane, R.A. Kinetics of base catalysed O-acylation of hydroxamic acids. Ind. J. of Chem. 2004; 43B:1983-1989. http://hdl.handle.net/123456789/21332.
25    Pathrikar, G.Y., Bondge, S.P., Burungle, A.S., Bhingolikar, V.E., Ingle, R.D., Mane, R A. Kinetics of condensation of aryl isothiocyanates with aryl amines. Ind. J. of Chem. 2002; 41A:2518-2521. http://hdl.handle.net/123456789/18447.
26    Thermokinetic Study of Thermal Degradation of Resin Derived from 1-Naphthol-4-sulphonic acid. Asian J. Research Chem. 2017; 10(6): 832-838. doi: 10.5958/0974-4150.2017.00139.0
27    Surendran Vijayaraj, Anoop Singh, Kokilam Perumal Sampathkumar. Pharmacokinetic Study of Oxime Prodrug of Gliclazide by LC-MS/MS Method in Rabbit Plasma. Asian J. Research Chem.2015; 8(5): 351-357. doi: 10.5958/0974-4150.2015.00058.9
28    Zaware B. H., Mane, R. A.; Ingle, D. B. Kinetics of reaction of chloroacetone with thioureas. Ind. J. Chem. Soc. 2000; 77: 214-216.
29    S. O. Mohod, D. T. Tayade. To Investigate the Temperature effect on Thermodynamic Parameters of substituted Thiocarbamidophenol in 60% Ethanol Water Mixture. Asian J. Research Chem. 2017; 10(2):191-193. doi: 10.5958/0974-4150.2017.00032.3.
30    K.T. Joshi, J.M. Patel, A.M. Pancholi, D.A. Shukla. Thermodynamic Parameters of Some Transition Metal ion Complexes of Some Substituted Hydrazones and Their Antibacterial Activity. Asian J. Research Chem. 2011; 4(6): 932-935. DOI: 10.5958/0974-4150
31    Pooja V. Jagasia, Divyadarshani B. Spectrophotometric Determination of Vitamin C in Pharmaceutical Preparations using Ammonium Metavanadate. Asian J. Research Chem. 2017; 10(3):341-344. doi: 10.5958/0974-4150.2017.00057.8
32    Gopalasatheeskumar K, Ariharasiva Kumar G, Sengottuvel T, Sanish Devan V, Srividhya V. Quantification of Total Phenolic and Flavonoid content in leaves of Cucumis melo var agrestis using UV- spectrophotometer. Asian J. Research Chem. 2019; 12(6):335-337. doi: 10.5958/0974-4150.2019.00062.2
33    Munde S. B., Bondge S. P., Bhingolikar V. E., Mane R. A. A facile synthesis of 1, 4-benzothiazines under solvent free conditions. Green Chem. 2003; 5: 278-279. https://doi.org/10.1039/B212042A.
34    Miyano S., Abe N., Sumoto T. K. Reactions of enamino-ketones. Part II. Synthesis of 4H-1,4-benzothiazines. J. Chem. Soc. Perkin Trans.1976; 10:039-040. https://doi.org/10.1039/P19760001146.
35    Gupta R. R., Kalwania G. S., Umar, R. Single Step Synthesis of 4H-1,4-Benzothiazines. Bull. Chem. Soc. Japan. 1984; 57(8):2343-2345. https://doi.org/10.1246/bcsj.57.2343.

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