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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Mini-Review Article

Various Synthetic Methods and Diverse Therapeutic Potential of Substituted Thiazine Derivatives

Author(s): Mohammad Asif*, Mamdouh Allahyani, Ahad Amer Alsaiari and Mazen Mohammed Almehmadi

Volume 27, Issue 20, 2023

Published on: 27 November, 2023

Page: [1741 - 1753] Pages: 13

DOI: 10.2174/0113852728260166231101070430

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Abstract

Heterocyclic compounds are currently of great interest in pharmaceutical research. Many natural products, including vitamins, hormones, and antibiotics, contain heterocyclic compounds, and these substances have grown in importance. Heterocyclic thiazine derivatives have numerous pharmacological actions, including anticancer, antimicrobial, antipsychotic, anti-mycobacterial, anti-fungal, antiviral, antimycobacterial, antioxidant, analgesic, antipyretic, anti-inflammatory activities, which is present in numerous substances. The N-CS linkage in its scaffold and the ease and economy of its synthesis methods have been key factors in the development of these molecules. Recently, numerous studies considering the various biological actions of thiazines have been published. Thiazine, a six-membered heterocyclic compound with nitrogen and sulfur in its ring system, has a wide range of chemical possibilities, which has encouraged insistent research into their various synthesis processes. The current review focuses on thiazine derivatives with potential biological activities.

Keywords: Thiazines, pharmacological activities, antimicrobial, analgesic, anti-inflammatory, anticancer, antipsychotic agent.

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[1]
Huang, S.; Pan, Y.; Zhu, Y.; Wu, A. A novel three-component one-pot reaction involving alkynes, urea or thiourea, and aldehydes. Org. Lett., 2005, 7(17), 3797-3799.
[http://dx.doi.org/10.1021/ol051458e] [PMID: 16092878]
[2]
Asif, M. Chemical and pharmacological potential of various substituted thiazine derivatives. J. Pharm. Appl. Chem., 2015, 1(2), 49-64.
[3]
El-Taweel, F.M.A.A.; Elnagdi, M.H. Chemo-/Regioselective synthesis of 6-unsubstituted dihydropyrimidinones, 1,3-thiazines and chromones via novel variants of biginelli reaction. J. Heterocycl. Chem., 2001, 38, 981.
[http://dx.doi.org/10.1002/jhet.5570380428]
[4]
Fu, L.; Ye, D.; Li, Y.; Yin, S. Synthesis and calming activity of 6H-2-amino-4-Aryl-6-(4-β-D-allopyranosyloxyphenyl)-1,3-thiazine. Chem. Nat. Compd., 2010, 46(2), 169-172.
[http://dx.doi.org/10.1007/s10600-010-9559-8]
[5]
Balenkova, E.S.; Nenajdenko, V.G. Preparation of α,β-unsaturated trifluoromethylketones and their application in the synthesis of heterocycles. Arkivoc, 2011, i, 246-328.
[6]
Dighade, A.S.; Dighade, S.R. Synthesis of substituted-4,6-diaryl-2-imino-diphenyl-6H- 1,3-thiazines. Pharma Chem., 2012, 4(5), 1863-1867.
[7]
Biehl, Ed.; Sathunuru, R. Facile synthesis of 4H-naphtho[2,3-e] derivatives of 1,3- thiazines and 1,3-selenazines and naphtha[2′,3′:4,5]derivatives of selenolo[2,3-b]pyridines and thieno[2,3-b]pyridines via 2,3-didehydrona-phthalene. Arkivoc, 2004, xiv, 51-60.
[8]
Yavari, I.; Nematpour, M.; Hossaini, Z. Ph3P-mediated one-pot synthesis of functionalized 3,4-dihydro-2H-1,3-thiazines from N,N′-dialkylthioureas and activated acetylenes in water. Monatsh. Chem., 2010, 141(2), 229-232.
[http://dx.doi.org/10.1007/s00706-009-0247-y]
[9]
Trofimova, T.P.; Zefirova, O.N.; Mandrugin, A.A.; Fedoseev, V.M.; Peregud, D.I.; Onufriev, M.V.; Gulyaeva, N.V.; Proskuryakov, S.Y. Synthesis and study of NOS-inhibiting activity of 2-N-acylamino-5,6-dihydro-4H-1,3-thiazine. Moscow Univ. Chem. Bull., 2008, 63(5), 274-277.
[http://dx.doi.org/10.3103/S0027131408050088]
[10]
Bhowmik, S.; Mishra, A.; Batra, S. A novel stereoselective one-pot synthesis of 2-susbstituted amino-5,6-dihydro-4H-1,3-thiazines via primary allylamines afforded from Morita–Baylis–Hillman acetates. RSC Advances, 2011, 1(7), 1237-1244.
[http://dx.doi.org/10.1039/c1ra00399b]
[11]
Sambhaji, P.V.; Shivraj, B.S. Simple and efficient synthesis of novel fused bicyclic heterocycles pyrimido-thiazine and their derivatives. Org. Chem. Curr. Res., 2012, 1(5), 1-3.
[12]
Nagaraj, A.; Sanjeeva Reddy, C. Synthesis and biological study of novel bis-chalcones, bis-thiazines and bis-pyrimidines. J. Indian Chem. Soc., 2008, 5(2), 262-267.
[http://dx.doi.org/10.1007/BF03246116]
[13]
Yadav, L.D.S.; Rai, V.K.; Yadav, B.S. The first ionic liquid-promoted one-pot diastereoselective synthesis of 2,5-diamino-/2-amino-5-mercapto-1,3-thiazin-4-ones using masked amino/mercapto acids. Tetrahedron, 2009, 65(7), 1306-1315.
[http://dx.doi.org/10.1016/j.tet.2008.12.050]
[14]
Feng, M.; Tang, B.; Liang, S.H.; Jiang, X. Sulfur-containing scaffolds in drugs: Synthesis and application in medicinal chemistry. Curr. Top. Med. Chem., 2016, 16(11), 1200-1216.
[http://dx.doi.org/10.2174/1568026615666150915111741] [PMID: 26369815]
[15]
Harper, J.; Khalil, I.; Shaw, L.; Bourguet-Kondracki, M.L.; Dubois, J.; Valentin, A.; Barker, D.; Copp, B. Structure-activity relationships of the bioactive thiazinoquinone marine natural products Thiaplidiaquinones A and B. Mar. Drugs, 2015, 13(8), 5102-5110.
[http://dx.doi.org/10.3390/md13085102] [PMID: 26266415]
[16]
Badshah, S.; Naeem, A. Bioactive thiazine and benzothiazine derivatives: Green synthesis methods and their medicinal importance. Molecules, 2016, 21(8), 1054.
[http://dx.doi.org/10.3390/molecules21081054] [PMID: 27537865]
[17]
Fu, P.; MacMillan, J.B. Thiasporines A-C, thiazine and thiazole derivatives from a marine-derived Actinomycetospora chlora. J. Nat. Prod., 2015, 78(3), 548-551.
[http://dx.doi.org/10.1021/np500929z] [PMID: 25584783]
[18]
Didwagh, S.; Pravina, B.P. Green synthesis of thiazine and oxazine derivatives-A short review. Int. J. Pharm. Sci. Res., 2013, 4(6), 2045-2061.
[19]
Simerpreet, S.; Singh, C.D. Synthesis and biological evaluation of 1,3-thiazine-A review. Pharmacophore, 2013, 4(3), 70-88.
[20]
Vincent, G.; Mathew, V.B.; Joseph, J.; Chandran, M.; Bhat, A.R.; Kumar, K.K. A review on biological activities of thiazine derivatives. Int. J. Pharm. Chem. Sci., 2014, 3(2), 341-348.
[21]
Begum, S.; Begum, A.; Sujatha, D.; Bharathi, K. Therapeutic utility of 1,3-thiazines-mini review. Saudi J. Med. Pharm. Sci., 2016, 2(12), 326-338.
[22]
Malve, H.; Kalra, S.; Zargar, A.H.; Jain, S.M.; Sethi, B.; Chowdhury, S.; Singh, A.K.; Thomas, N.; Unnikrishnan, A.G.; Thakkar, P.B. Diabetes insipidus: The other diabetes. Indian J. Endocrinol. Metab., 2016, 20(1), 9-21.
[http://dx.doi.org/10.4103/2230-8210.172273] [PMID: 26904464]
[23]
Alcarraz-Vizán, G.; Casini, P.; Cadavez, L.; Visa, M.; Montane, J.; Servitja, J.M.; Novials, A. Inhibition of BACE2 counteracts hIAPP‐induced insulin secretory defects in pancreatic β‐cells. FASEB J., 2015, 29(1), 95-104.
[http://dx.doi.org/10.1096/fj.14-255489] [PMID: 25342134]
[24]
Beauchamp, J.; Benardeau, A.; Hilpert, H.; Wang, H. 2-aminodihydro [1,3] thiazines as BACE 2 inhibitors for the treatment of diabetes.World Intellectual Property Organization; , 2011.
[25]
Brodney, M.A.; Beck, E.M.; Butler, C.R.; Davoren, J.E. Alkyl-substituted hexahydro-pyrano3[1,3]thiazin-2-amine compounds and their use in the treatment of neurodegenerative diseases, including AD, as well as the treatment of diabetes and obesity. US Patent 8822456B2 2014.
[26]
Thakur, A.S.; Deshmukh, R.; Jha, A.K.; Sudhir Kumar, P. Synthesis and oral hypoglycemic effect of novel thiazine containing trisubstituted benzenesulfonylurea derivatives. Saudi Pharm. J., 2015, 23(5), 475-482.
[http://dx.doi.org/10.1016/j.jsps.2014.11.017] [PMID: 26594112]
[27]
Faidallah, H.M.; Khan, K.A.; Asiri, A.M. Synthesis and biological evaluation of new 3-trifluoromethylpyrazolesulfonyl-urea and thiourea derivatives as antidiabetic and antimicrobial agents. J. Fluor. Chem., 2011, 132(2), 131-137.
[http://dx.doi.org/10.1016/j.jfluchem.2010.12.009]
[28]
Meyer-Kirchrath, J.; Schrör, K. Cyclooxygenase-2 inhibition and side-effects of non-steroidal anti-inflammatory drugs in the gastrointestinal tract. Curr. Med. Chem., 2000, 7(11), 1121-1129.
[http://dx.doi.org/10.2174/0929867003374219] [PMID: 11032962]
[29]
Zarghi, A.; Zebardast, T.; Daraie, B.; Hedayati, M. Design and synthesis of new 1,3-benzthiazinan-4-one derivatives as selective cyclooxygenase (COX-2) inhibitors. Bioorg. Med. Chem., 2009, 17(15), 5369-5373.
[http://dx.doi.org/10.1016/j.bmc.2009.06.056] [PMID: 19596198]
[30]
Tozkoparan, B.; Aktay, G.; Yeşilada, E. Synthesis of some 1,2,4-triazolo[3,2-b]-1,3-thiazine-7-ones with potential analgesic and antiinflammatory activities. Farmaco, 2002, 57(2), 145-152.
[http://dx.doi.org/10.1016/S0014-827X(01)01195-8] [PMID: 11902657]
[31]
Bózsing, D.; Sohár, P.; Gigler, G.; Kovács, G. Synthesis and pharmacological study of new 3,4-dihydro-2H,6H-pyrimido-[2,1-b][1,3]thiazines. Eur. J. Med. Chem., 1996, 31(9), 663-668.
[http://dx.doi.org/10.1016/0223-5234(96)85874-0]
[32]
Srikanth, J.; Sandeep, T.; Divya, K.; Govindarajan, R. Screening of in vitro antiinflammatory activity of some newly synthesized 1,3-thiazine derivatives. Int. J. Res. Pharm. Chem., 2013, 3(2), 213-220.
[33]
Raja Sekhar, K.; Raj Kumar, P.; Reddy, S.; Umasankar, K.; Gomathi, K. Analgesic and anti-inflammatory activities of novel thiazine derivatives. World J. Pharm. Res., 2001, 3(3), 4464-4473.
[34]
Vijay, V.D. Synthesis of chalcones, 1,3-thiazines and the biological evaluvation for antiinflammatory, analgesic and ulcerogenic activity. Pharm. Res., 2011, 5(1), 127-143.
[35]
Ziakas, G.N.; Rekka, E.A.; Gavalas, A.M.; Eleftheriou, P.T.; Kourounakis, P.N. New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents. Bioorg. Med. Chem., 2006, 14(16), 5616-5624.
[http://dx.doi.org/10.1016/j.bmc.2006.04.030] [PMID: 16690318]
[36]
Ingarsal, N.; Amutha, P.; Nagarajan, S. Synthesis and antibacterial activities of some 2-amino-4-(1,1′-biphenyl-4-yl)-6-aryl-6H-1,3-thiazines. J. Sulfur Chem., 2006, 27(5), 455-459.
[http://dx.doi.org/10.1080/17415990600904705]
[37]
Didwagh, S.S.; Piste, P.B.; Burungale, A.S.; Nalawade, A.M. Synthesis and antimicrobial evaluation of novel 3-(4,6-diphenyl-6H-1,3-thiazin-2-yl)-2-(4-methoxyphenyl)thiazolidin-4-one derivatives. J. Appl. Pharm. Sci., 2013, 3(11), 122-127.
[38]
Singh, U.P.; Pathak, M.; Dubey, V.; Bhat, H.R.; Gahtori, P.; Singh, R.K. Design, synthesis, antibacterial activity, and molecular docking studies of novel hybrid 1,3-thiazine-1,3,5-triazine derivatives as potential bacterial translation inhibitor. Chem. Biol. Drug Des., 2012, 80(4), 572-583.
[http://dx.doi.org/10.1111/j.1747-0285.2012.01430.x] [PMID: 22702334]
[39]
Tony, G.; Chandran, M.; Bhat, A.R.; Krishnakumar, K. Molecular docking studies: 1, 3-thiazine and 1,3-oxazine derivatives. J. Pharm. Res., 2014, 8(2), 136-138.
[40]
Babu, K.; Selvi, D.; Pitchai, P. Synthesis and microbial studies of novel 1,3-thiazine compounds bearing Schiff base moiety. Pharma Chem., 2015, 7(10), 89-92.
[41]
Rathod, S.P.; Charjan, A.P.; Rajput, P.R. Synthesis and antibacterial activities of chloro substituted-1, 3-thiazines. Rasayan J. Chem., 2010, 3(2), 363-367.
[42]
Prakash, N.; Sivagami, S.; Ingarsal, N. A novel bromonaphthyl based 2-amino-1,3-thiazines: synthesis, characterization with in vitro antimicrobial screening. Res. J. Chem. Sci., 2015, 5(7), 8-11.
[43]
Beena, K.P.; Sooraj, K.V.; Abraham, N.S.; Akelesh, T. Synthesis, characterization and evaluation of some 1, 3 thiazine derivatives as possible antimicrobial agents. Am. J. Pharmtech. Res., 2013, 3(4), 734-740.
[44]
Bhangale, L.P.; Sawant, R.L.; Wadekar, J.B. Topliss modified approach for design and synthesis of 1,3 thiazines as antimicrobials. Int. J. Drug Design Discov., 2011, 2(4), 637-641.
[45]
Deshmukh, R. Synthesis, structural study and biological evaluation of 1,3-thiazine. Der Chemica Sinica., 2015, 6(3), 59-63.
[46]
Dipansu, G.S.; Mander, B.P. Synthesis, characterization and biological evaluation of some novel 4, 6-disubstituted-1,3-thiaizne derivatives for their antibacterial activity. Inter. J. Health Pharm. Sci., 2012, 1(1), 27-33.
[47]
Edayadulla, N.; Ramesh, P. Synthesis and physiological evaluation of new N-nitroso-2,6-dicarbethoxy-3,5-diaryltetrahydro-1,4-thiazine-1,1-dioxides. Med. Chem. Res., 2012, 21(8), 2056-2063.
[http://dx.doi.org/10.1007/s00044-011-9729-7]
[48]
Farooque, H.Z.H. synthesis and anti-microbial screening of some 1,3-thiazine derivatives. J. Chem. Pharm. Res., 2012, 4(4), 2263-2267.
[49]
Varalakshmi Devi, P.; Ramesh, G.P.; Keerthi, K.; Ramkrishna, G. Synthesis and biological evaluation of different Thiazine derivatives. J. Pharm. Res., 2011, 4(1), 274-275.
[50]
Koketsu, M.; Tanaka, K.; Takenaka, Y.; Kwong, C.D.; Ishihara, H. Synthesis of 1,3-thiazine derivatives and their evaluation as potential antimycobacterial agents. Eur. J. Pharm. Sci., 2002, 15(3), 307-310.
[http://dx.doi.org/10.1016/S0928-0987(02)00014-3] [PMID: 11923063]
[51]
Ali, T.E.S.; El-Kazak, A.M. Synthesis and antimicrobial activity of some new 1,3-thiazoles, 1,3,4-thiadiazoles, 1,2,4-triazoles and 1,3-thiazines incorporating acridine and 1,2,3,4-tetrahydroacridine moieties. Eur. J. Chem., 2010, 1(1), 6-11.
[http://dx.doi.org/10.5155/eurjchem.1.1.6-11.12]
[52]
Bhangale, L.P.; Sawant, R.L.; Wadekar, J.B. Topliss modified approach for design and synthesis of 1,3 thiazines as antimicrobials. Int. J. Drug Design Dis., 2011, 2(4), 637-641.
[53]
Haider, F.H.Z. Synthesis and antimicrobial screening of some 1,3-thiazines. J. Chem. Pharm. Res., 2012, 4(4), 2263-2267.
[54]
Thanusu, J.; Kanagarajan, V.; Gopalakrishnan, M. Synthesis, spectral characterization, and in vitro antibacterial and antifungal activities of novel 1,3-thiazine-2-amines comprising morpholine nucleus. J. Enzyme Inhib. Med. Chem., 2010, 25(6), 756-764.
[http://dx.doi.org/10.3109/14756360903389898] [PMID: 20590407]
[55]
Abdalla, M.; Gomha, S.; Abd El-Aziz, M.; Serag, N. Synthesis and evaluation of some novel thiazoles and 1,3-thiazines as potent agents against the rabies virus. Turk. J. Chem., 2016, 40, 441-453.
[http://dx.doi.org/10.3906/kim-1506-13]
[56]
Shadia, A.G.S.; Naemel, E.I. Novel benzimidazole(2,1.c)[1,4]thiazinone derivatives with potent activity against HSV-1. Arch. Pharm. Chem. Life Sci, 2011, 11, 255-263.
[57]
Wang, W.; Zhao, B.; Xu, C.; Wu, W. Synthesis and antitumor activity of the thiazoline and thiazine multithioether. Int. J. Org. Chem., 2012, 2(2), 117-120.
[http://dx.doi.org/10.4236/ijoc.2012.22018]
[58]
Abdelhamid, A.O.; Shawali, A.S.; Gomha, S.M.; El-Enany, W.A.M.A. Synthesis and in vitro anti-breast cancer evaluation of some novel 1, 3-thiazines and thiazolone derivatives incorporating pyrazole moiety. World J. Pharm. Pharm. Sci., 2015, 4(9), 1695-1705.
[59]
Blokhina, S.V.; Volkova, T.V.; Ol’khovich, M.V.; Sharapova, A.V.; Proshin, A.N.; Bachurin, S.O.; Perlovich, G.L. Synthesis, biological activity, distribution and membrane permeability of novel spiro-thiazines as potent neuroprotectors. Eur. J. Med. Chem., 2014, 77, 8-17.
[http://dx.doi.org/10.1016/j.ejmech.2014.02.052] [PMID: 24607585]
[60]
Ravindar, B.; Murthy, S.M.; Shaik, A.B. Design, facile synthesis, and biological evaluation of novel 1,3-thiazine derivatives as potential anticonvulsant agents. Asian J. Pharm. Clin. Res., 2016, 9(5), 272-276.
[http://dx.doi.org/10.22159/ajpcr.2016.v9i5.13676]
[61]
Jagodziński, T.S.; Wesołowska, A.; Jagodzińska, E.; Rump, S. Synthesis and biological activity of certain novel derivatives of 1H-pyrrolo[1,2-c][1,3]thiazine. Acta Pol. Pharm., 2003, 60(1), 67-73.
[PMID: 12848370]
[62]
Hushare, J.; Rajput, P.R.; Ghodile, N.G.; Malpani, M.O. Synthesis, characterization of some novel heterocycles and their growth-promoting effect on some flowering plants. Int. J. Pharm. Tech. Res., 2013, 5(2), 420-425.
[63]
Kieć-Kononowicz, K.; Karolak-Wojciechowska, J.; Müller, C.E.; Schumacher, B.; Pękala, E.; Szymańska, E. Imidazo-thiazine, -diazinone and -diazepinone derivatives. Synthesis, structure and benzodiazepine receptor binding. Eur. J. Med. Chem., 2001, 36(5), 407-419.
[http://dx.doi.org/10.1016/S0223-5234(01)01239-9] [PMID: 11451530]
[64]
Al-Difar, H.A.; Elarfi, M.J. Synthesis of some heterocyclic compounds derived from chalcones. Sci. Rev. Chem. Comm., 2012, 2(2), 103-107.
[65]
Zawisza, T.; Matczak, H.; Kowalczyk-Bronisz, S.H.; Jakóbiec, T. Syntheses and pharmacological analysis of new derivatives of tetrahydro-[1,3]-thiazine and 2-thiobarbituric acid. Arch. Immunol. Ther. Exp., 1981, 29(2), 235-248.
[PMID: 7030266]
[66]
Zawisza, T.; Wagner, E.; Matczakowa, H.; Jakóbiec, T. Studies on derivatives of tetrahydro [1,3]-thiazine. Arch. Immunol. Ther. Exp., 1978, 26(1-6), 943-949.
[PMID: 749843]
[67]
Dabholkar, V.V.; Parab, S.D. Synthesis of chalcones, 1,3-thiazines and 1,3-pyrimidines derivatives and their biological evaluation for anti-inflammatory, analgesic and ulcerogenic activity. J. Neonatol., 2011, 1(2), 176-188.
[68]
Margulies, L.; Margulies, L.; Rozen, H. Photostabilization of a nitromethylene heterocycle insecticide on the surface of montmorillonite. Clays Clay Miner., 1988, 36(2), 159-164.
[http://dx.doi.org/10.1346/CCMN.1988.0360210]
[69]
Bourzat, J.D.; Farge, D.; Leger, A.; Ponsinet, G. Perhydro-1,3-thiazine derivatives. US Patent 4271156 1981.
[70]
Ram, S.G.; Rajesh, P.G.; Parhate, V.V. Synthesis, charecterization and antibacterial activities of some new bromo/nitro 1,3-thiazines. Rasayan J. Chem., 2013, 6, 65-67.
[71]
Kadhim, M.A. Synthesis and chemical characterization of some novel azachalcones compounds and evaluation of their biological activity. J. Uni. Anbar for Pure Sci., 2010, 4(3), 40-43.
[72]
Kalirajan, R.; Sivakumar, S.U.; Jubie, S.; Gowramma, B.; Suresh, B. Synthesis and biological evaluation of some heterocyclic derivatives of chalcones. In. J. ChemTech. Res., 2009, 1(1), 27-34.
[73]
Mandolesi Sá, M.; Ferreira, M.; Bortoluzzi, A.J.; Fernandes, L.; Cunha, S. Exploring the reaction of multifunctional allylic bromides with N,S-dinucleophiles:isothiuronium salts and analogs as useful motifs to assemble the 1,3-thiazine core. Arkivoc, 2010, xi, 303-321.
[74]
Glotova, T.E.; Komarova, T.N.; Nakhmanovich, A.S.; Lopyrev, V.A. Synthesis of substituted 2-amino-1,3-thiazine-6-thiones. Russ. Chem. Bull., 2000, 49(11), 1917-1918.
[http://dx.doi.org/10.1007/BF02494937]
[75]
Fisyuk, A.S.; Peretokin, N.V.; Unkovsky, B.V. New approach to the synthesis of 1,3-chloroisothiocyanatoalkanes. Synthesis of tetrahydro-1,3-thiazine-2-thiones and 2-alkyl amino-5, 6-dihydro-1,3-thiazines. Chem. Heterocycl. Compd., 2003, 39(6), 802-808.
[http://dx.doi.org/10.1023/A:1025663616439]
[76]
Yadav, L.D.S.; Yadav, S.; Rai, V.K. Mercaptoacetic acid based expeditious synthesis of polyfunctionalised 1,3-thiazines. Tetrahedron, 2005, 61(42), 10013-10017.
[http://dx.doi.org/10.1016/j.tet.2005.08.021]
[77]
Siddiqui, I.R.; Singh, J.; Singh, P.K.; Srivastava, V. Facile synthesis of acyclic analogues of carbocyclic nucleoside as potential anti-HIV pro-drug. Indian J. Chem., 2010, 49B, 512-520.
[78]
Vigante, B.; Ozols, J.; Mishnev, A.; Duburs, G.; Chekavichus, B. Formation of derivatives of 5,6-dihydro-1,3-thiazines in the reaction of acetothioacetic acid ethyl ester under the conditions of the Hantzsch synthesis. Chem. Heterocycl. Compd., 2000, 36(7), 862-869.
[http://dx.doi.org/10.1007/BF02256924]
[79]
Trofimova, T.P.; Fedoseev, V.M.; Tkachenko, S.E. Synthesis and rearrangement of 5-halo-3,4,5,6-tetrahydro-1,3-thaizine-2-thiones and 5-halomethylthiazolidine-2-thiones. Chem. Heterocycl. Compd., 2002, 38(12), 1533-1534.
[http://dx.doi.org/10.1023/A:1022614132457]
[80]
Kruithof, A.; Ploeger, M.L.; Janssen, E.; Helliwell, M.; Kanter, F.J.J.; Ruijter, E.; Orru, R.V.A. Multicomponent synthesis of 3,6-dihydro-2H-1,3-thiazine-2-thiones. Molecules, 2012, 17(2), 1675-1685.
[http://dx.doi.org/10.3390/molecules17021675] [PMID: 22318323]
[81]
Hassan, A.; Nour El-Din, A.; Abdel-Latif, F.; Mostafa, S.; Bräse, S. Formation of dioxospiroindene[1,3]thiazine and thioxoindeno[2,1-d]imidazolone derivatives from alkenylidene-hydrazinecarbothioamides. Chem. Pap., 2012, 66(4), 295-303.
[http://dx.doi.org/10.2478/s11696-012-0145-3]
[82]
Peudru, F.; Legay, R.; Lohier, J.F.; Reboul, V.; Gulea, M.; Gulea, M. Facile access to γ-aminothiols from 1,3-thiazines via a microwave-assisted three-component reaction. Tetrahedron, 2012, 68(44), 9016-9022.
[http://dx.doi.org/10.1016/j.tet.2012.08.072]
[83]
Yuskovets, V.N.; Moskvin, A.V.; Ivin, B.A. New method of synthesis of 5-acyl-1,3-thiazines. Russ. J. Gen. Chem., 2004, 74(2), 312-313.
[http://dx.doi.org/10.1023/B:RUGC.0000025527.63179.ae]
[84]
Rašović, A.; Steel, P.J.; Kleinpeter, E.; Marković, R. Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S⋯O interactions. Tetrahedron, 2007, 63(9), 1937-1945.
[http://dx.doi.org/10.1016/j.tet.2006.12.075]
[85]
Yadav, L.D.S.; Singh, A. Microwave activated solvent-free cascade reactions yielding highly functionalised 1,3-thiazines. Tetrahedron Lett., 2003, 44(30), 5637-5640.
[http://dx.doi.org/10.1016/S0040-4039(03)01353-4]

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