Synthetic Strategies of Benzothiazines: A Mini Review

Author(s): Shafia Mir, Ayaz Mahmood Dar, Bashir Ahmad Dar*

Journal Name: Mini-Reviews in Organic Chemistry

Volume 17 , Issue 2 , 2020


DOI : 10.2174/1570193X16666181206101439

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Abstract:

Benzothiazine is a heterocyclic compound consisting of a benzene ring attached to the 6- membered thiazine ring. The benzothiazines constitute the group of heterocyclic compounds as they have found a variety of industrial uses and show promise as herbicides. Besides this, benzothiazines play an important role in the field of drug discovery as they have the potential to act as drug candidates for the treatment of a large number of diseases including, cancer, vasorelaxant, diabetic, hypertension, mycotic infection and microbial infection. The presence of nitrogen-sulphur axis and similarity in the structure with phenothiazine drugs help the benzothiazines to act as drugs for the treatment of a number of diseases. Herein, we represent different synthetic strategies for the simple and multi-component synthesis of benzothiazine heterocyclic derivatives. The strategies mostly involve the use of 2-aminothiophenol, 1, 3-dicarbonyl compounds or α-haloketones. In almost all the strategies, the potential yields have been obtained.

Keywords: 2-Aminothiophenol, buchwald coupling, multi-component, benzothiazine, heterocyclic compounds, phenothiazine.

[1]
Love, B.; Kormendy, M.F. Sulfostyril (2,1-benzothiazine 2,2-dioxide). I. Preparation and reactions of 3,4-dihydrosulfostyril. J. Org. Chem., 1965, 30, 3163-3163.
[http://dx.doi.org/10.1021/jo01020a071]
[2]
Prota, G.; Ponsiglione, E.; Ruggiero, R. Synthesis and photochromism of Δ2,2′-BI-(2H-1,4-benzothiazine). Tetrehedron, 1974, 30, 2781-2781.
[http://dx.doi.org/10.1016/S0040-4020(01)97445-9]
[3]
Corona, L.D.; Signorelli, G.; Pinzetta, A.; Coppi, G. Synthesis and immune stimulating activity of new 1,4-benzothiazine derivatives. Eur. J. Med. Chem., 1992, 27, 419-423.
[http://dx.doi.org/10.1016/0223-5234(92)90157-V]
[4]
Farag, A.M.; Shawali, A.S.; Algharib, M.S.; Dawood, K.M. One-step synthesis of novel 2,2′-bi(4,5-dihydro-1,3,4-thiadiazole) and 2,3-disubstituted 1,4-benzothiazine derivatives. Tetrahedron, 1994, 50, 5091-5091.
[http://dx.doi.org/10.1016/S0040-4020(01)90419-3]
[5]
Napolitano, A.; Costantini, C.; Crescenzi, O.; Prota, G. Characterisation of 1,4-benzothiazine intermediates in the oxidative conversion of 5-S-cysteinyldopa to pheomelanins. Tetrahedron Lett., 1994, 35, 6365-6368.
[http://dx.doi.org/10.1016/S0040-4039(00)73434-4]
[6]
Guarda, V.L.; Perrissin, M.; Thomasson, F.; Ximenes, E.A.; Galdino, S.L.; Pitta, I.R.; Luu-Duc, C.; Barbe, J. Synthesis of 4-octyl-2H-1,4-benzo-thiazin-3-ones. Eur. J. Med. Chem., 2003, 38(7-8), 769-773.
[http://dx.doi.org/10.1016/S0223-5234(03)00127-2] [PMID: 12932908]
[7]
Esmaili, A.A.; Ghereghloo, M.; Islami, M.R.; Bijanzadeh, H.R. One-pot synthesis of stable phosphonium ylides using 2-aminothiophenol. Tetrahedron, 2003, 59, 4785-4788.
[http://dx.doi.org/10.1016/S0040-4020(03)00693-8]
[8]
Matysiak, J. Synthesis, antiproliferative and antifungal activities of some 2-(2,4-dihydroxyphenyl)-4H-3,1-benzothiazines. Bioorg. Med. Chem., 2006, 14(8), 2613-2619.
[http://dx.doi.org/10.1016/j.bmc.2005.11.053] [PMID: 16377195]
[9]
Madrid, P.B.; Polgar, W.E.; Toll, L.; Tanga, M.J. Synthesis and antitubercular activity of phenothiazines with reduced binding to dopamine and serotonin receptors. Bioorg. Med. Chem. Lett., 2007, 17(11), 3014-3017.
[http://dx.doi.org/10.1016/j.bmcl.2007.03.064] [PMID: 17407813]
[10]
Bakavoli, M.; Nikpour, M.; Rahimizadeh, M.; Saberi, M.R.; Sadeghian, H. Design and synthesis of pyrimido[4,5-b][1,4]benzo-thiazine derivatives, as potent 15-lipoxygenase inhibitors. Bioorg. Med. Chem., 2007, 15(5), 2120-2126.
[http://dx.doi.org/10.1016/j.bmc.2006.12.022] [PMID: 17210254]
[11]
Tandon, V.K.; Maurya, H.K.; Mishra, N.N.; Shukla, P.K. Design, synthesis and biological evaluation of novel nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents. Eur. J. Med. Chem., 2009, 44(8), 3130-3137.
[http://dx.doi.org/10.1016/j.ejmech.2009.03.006] [PMID: 19349095]
[12]
Pratap, U.R.; Jawale, D.V.; Londhe, B.S.; Mane, R.A. Baker’s yeast catalyzed synthesis of 1, 4-benzothiazines, performed under ultrasonication. J. Mol. Cat. B, 2011, 68, 94-97.
[http://dx.doi.org/10.1016/j.molcatb.2010.09.018]
[13]
Alam, M.; Khan, S.; Khan, M.S. A Facile synthesis of 6,7-fused steroidal thiazoles via 1,3-intramolecular migration of bromine/allylic displacement of bromine. J. Chil. Chem. Soc., 2008, 53, 1714-1717.
[http://dx.doi.org/10.4067/S0717-97072008000400017]
[14]
Khan, A.; Alam, M.; Mushfiq, M. The synthesis of 2′-amino-5α-cholest-6-eno [6, 7-d] thiazole derivatives under microwave irradiation using dry-media conditions. Chin. Chem. Lett., 2008, 19, 1027-1030.
[http://dx.doi.org/10.1016/j.cclet.2008.06.021]
[15]
Kumar, M.; Sharma, K.; Samarth, R.M.; Kumar, A. Synthesis and in vitro anti-proliferative activity of novel 12(H)-quino[3,4-b][1,4]benzothiazine derivatives. Eur. J. Med. Chem., 2010, 45, 4158-4163.
[16]
Zav’yalov, S.I.; Kravchenko, N.E.; Ezhova, G.I.; Kulikova, L.B.; Zavozin, A.G.; Dorofeeva, O.V. Synthesis of 2-aminothiazole derivatives. J. Pharm. Chem., 2007, 41(2), 105-108.
[http://dx.doi.org/10.1007/s11094-007-0023-4]
[17]
Shamsuzzaman, A.M.; Khanam, D.H.; Gatoo, M.A. Anticancer and antimicrobial evaluation of newly synthesized steroidal 5,6 fused benzothiazines. Arab. J. Chem., 2014, 7, 461-468.
[http://dx.doi.org/10.1016/j.arabjc.2013.06.027]
[18]
Gautam, N.; Ajmera, N.; Gupta, S.; Gautam, D.C. Synthesis, spectral characterization and pharmaceutical importance of novel 4h-1, 4-benzothiazines, and their sulfone analogues. Eur. J. Chem., 2012, 3(1), 106-111.
[http://dx.doi.org/10.5155/eurjchem.3.1.106-111.489]
[19]
Lin, Y-M.; Lu, G-P.; Wang, R-K.; Yi, W-B. Radical route to 1,4-benzothiazine derivatives from 2-aminobenzenethiols and ketones under transition-metal-free conditions. Org. Lett., 2016, 18(24), 6424-6427.
[http://dx.doi.org/10.1021/acs.orglett.6b03324] [PMID: 27978628]
[20]
Gimbert, C.; Vallribera, A. A straightforward synthesis of benzothiazines. Org. Lett., 2009, 11(2), 269-271.
[http://dx.doi.org/10.1021/ol802346r] [PMID: 19072228]
[21]
Swaroop, D.K.; Kumar, N.R.; Ratnakarreddy, K.; Raja, G.; Srigiridhar, K.; Poornachandra, Y.; Kumar, C.G.; Babu, N.J.; Kumar, G.S.; Narsaiah, B. Novel 1,2,3-triazole-functionalized 1,2-benzothiazine 1,1-dioxide derivatives: Regioselective synthesis, biological evaluation and docking studies. ChemistrySelect, 2018, 3, 2398-2403.
[http://dx.doi.org/10.1002/slct.201800072]
[22]
Saadouni, M.; Ghailane, T.; Boukhris, S.; Hassikou, A.; Habbadi, N.; Ghailane, R.; Harcharras, M.; Souizi, A.; Amri, H. Regioselective synthesis of new variety of 1,4-benzothiazines. Org. Commun, 2014, 7(2), 77-84.
[23]
Harmata, M.; Rayanil, K.O.; Espejo, V.R.; Barnes, C.L. Benzothiazines in synthesis. Further studies of the intramolecular, stereoselective addition of sulfonimidoyl carbanions to α,β-unsaturated functional groups. J. Org. Chem., 2009, 74(8), 3214-3216.
[http://dx.doi.org/10.1021/jo900151d] [PMID: 19284723]
[24]
Rai, A.; Raj, V.; Singh, A.K.; Keshari, A.K.; Kumar, U.; Kumar, D.; Saha, S. Design and synthesis of 1,4-benzothiazine derivatives with promising effects against colorectal cancer cells. Cogent. Chem., 2017, 3 1303909
[http://dx.doi.org/10.1080/23312009.2017.1303909]


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Article Details

VOLUME: 17
ISSUE: 2
Year: 2020
Published on: 28 February, 2020
Page: [148 - 157]
Pages: 10
DOI: 10.2174/1570193X16666181206101439
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