2-Substitutedguanidino-4-substitutedimine-6-substitutedimino-1,3,5-thia-diazines (VIIIa-r) were successfully isomerised into 1-substituted-2-sub-stitutedguanidino-4-substitutedimine-6-thio-1,3,5-triazines or 1-methyl-3-(1- substituted-4-{[(E)-substitutedmethylidene]amino}-6-thioxo-1,6-dihydro-1,3,5-triazin-2-yl)guanidines (IXa-r) by refluxing with 10% aqueous ethanolic sodium bicarbonate medium. The structure of all the synthesized compounds was justified on the basis of chemical characteristics, elemental analysis and spectral analysis

P. V. Raut*, P. S. Bodakhe, S. A. Waghmare, D. T. Tayade

English

ZENODO

IAJPS 2017, 4 (12), 4293-4300                          P. V. Raut et al                       ISSN 2349-7750    w w w . i a j p s . c o m   Page 4293  CODEN [USA]: IAJPBB                    ISSN: 2349-7750 AMERICAN JOURNAL OF   PHARMACEUTICAL SCIENCES    Available online at: http://www.iajps.com                           Research Article  SYNTHESIS OF 1-SUBSTITUTED-2-SUBSTITUTEDGUANIDINO-4-SUBSTITUTEDIMINE-6-THIO-1,3,5-TRIAZINES P. V. Raut1*, P. S. Bodakhe2, S. A. Waghmare3, D. T. Tayade4, 1Smt Sarda college Anjangaon (Surji), Dist. Amaravati (MS) 444728. 2Department of Chemistry, Vidya Bharti Mahavidhyalaya, Amravati 444606. 3Ghaulam Nabi Azad Arts, Comm. & Science College, Barshitakli Dist. Akola, (MS) 444401. 4Govt. Vid. Institute of Science and Humanities, Amravati (MS) 444606. Abstract: 2-Substitutedguanidino-4-substitutedimine-6-substitutedimino-1,3,5-thia-diazines (VIIIa-r) were successfully isomerised into 1-substituted-2-sub-stitutedguanidino-4-substitutedimine-6-thio-1,3,5-triazines or 1-methyl-3-(1-substituted-4-{[(E)-substitutedmethylidene]amino}-6-thioxo-1,6-dihydro-1,3,5-triazin-2-yl)guanidines (IXa-r) by refluxing with 10% aqueous ethanolic sodium bicarbonate medium. The structure of all the synthesized compounds was justified on the basis of chemical characteristics, elemental analysis and spectral analysis. Corresponding author:  P. V. Raut,  Smt Sarda college Anjangaon (Surji),  Dist. Amaravati (MS) 444728. E- mail: pavanraut5@rediffmail.com    Please cite this article in press as P. V. Raut et al., Synthesis Of 2-Substitutedguanidino-4-Substituted-Imine- 6-Substitutedimino-1,3,5-Thiadiazines, Indo Am. J. P. Sci, 2017; 4(12).          QR code   IAJPS 2017, 4 (12), 4293-4300                          P. V. Raut et al                       ISSN 2349-7750    w w w . i a j p s . c o m   Page 4294 INTRODUCTION: The 1,3,5-triazine nucleus containing compounds have gained immense importance in human life due to their varieties of applications in medicinal, industrial pharmaceutical and agricultural fields1-5. These 1,3,5-triazines have their own identity and importance in medicinal6, pharmaceutical7, agricultural8 and industrial9 fields. Some S-triazines possesses antidiabetic10-11, anti-tumor12-15, anti-inflammatory16, anti-depresent17, hypoglycaemic18 activities.  They are also used as herbicidal19-25, fungicidal26-28, insecticidal29, anti-corrosive, antimicrobial, anti-convulsant and anti-oxidant properties.   Hence it was thought interesting to carry out the isomerisation of 2-substitutedguanidino-4-substitutedimine-6-substitutedimino-1,3,5-thiadiazines (VIIIa-r) into 1-substituted-2-substituted guanidino-4-substitutedimine-6-thio-1,3,5-triazines (IXa-r) in the presence of  10% ethanolic sodium bicarbonate medium. The tentative reaction for the formation of product is depicted below.   N SNR NCHN R"HN C NHR'NHN NNR NCHSR"HN C NHR'NH2-Substitutedguanidino-4-substitutedimine-6-substitutedimino-1,3,5-thiadiazine1-Substituted-3-[(2Z)-2-(substitutedimino)-4-{[(E)-substituted-methylidene]amino}2H-1,3,5-thiadiazin-6-yl]guanidine1-Substituted-2-substitutedguanidino-4-substitutedimine-6-thio-1,3,5-triazine1-Methyl-3-(1-substituted-4-{[(E)-substitutedmethylidene]-amino}-6-thioxo-5,6-dihydro-1,3,5-triazin-2-yl]guanidineORIsomerisation(VIIIa-r) (IXa-r)ORWhere R, R' = -methyl, -ethyl, -phenyl, -3-nitrobenzene, -4nitrobenzene, -p-dimethylaniline.                           R" = -ethyl, -phenyl, p-chlorophenyl. Reaction Scheme-1 EXPERIMENTAL: Synthesis of 1-phenyl-2-phenylguanidino-4-methylimine-6-thio-1,3,5-triazine (IXa): 2-Phenylguanidino-4-methylimino-6-phenylimino-1,3,5-thiadiazine (VIIIa) was suspended in 5% ethanolic sodium bicarbonate solution and refluxed for half an hour on water bath. During heating the reactant went into the solvent. After distillation of excess solvent milky white colour crystals were isolated. It was recrystallised from glacial acetic acid to obtain (IXa), yield 78%, m.p. 1250C. The probable reaction mechanism for the formation of (IXa) may be as depicted below (Scheme-2).  N SNNCHN PhHN C NHPhNHH3CN NNH3C NCHSPhHN C NHPhNH2-Phenylguanidino-4-methylimine-6-phenylimino-1,3,5-thiadiazineIsomerisation(VIIIa)1-Phenyl-2-phenylguanidino-4-methylimine-6-thio-1,3,5-triazine(IXa) Reaction Scheme-2    IAJPS 2017, 4 (12), 4293-4300                          P. V. Raut et al                       ISSN 2349-7750    w w w . i a j p s . c o m   Page 4295 RESULTS & DISCUSION: Properties of (IXa): 1) It was milky white crystalline solid having m.p.1250C. 2) It gave positive test for nitrogen and sulphur. 3) It was desulphurized when boiled with alkaline plumbite solution. 4) It was soluble in benzene, acetic acid, DMF, dioxane and DMSO. 5) It gave positive test for imino group. 6) Elemental analysis: The result of elemental analysis is given in following table-1 Elements Found (%) Calculated (%) Carbon 49.89 51.82 Hydrogen 3.92 4.98 Nitrogen 31.55 32.55 Sulphur 10.28 10.63 7) From the analytical data the molecular formula was found to be C13H15N7S1. 8) IR Spectrum of compound:  IR spectrum of compound was carried out in KBr pellets and the important absorptions are correlated as follows and are depicted as fallowing table-2. Absorption observed in(cm-1) Assignment Absorption Expected in (cm-1) 3389.6 NH stretching30 3500-3300 1635.6 C=N stretching ring 1600-1430 109026 C-N stretching32 1200-1000 1254.24 C=S stretching33 1500-1200 669.28 Monosubstituted benzene 34 800-600 1509.14 Ar C=C Stretch 1600-1475  9) PMR-Spectrum: The PMR spectrum of compound was carried out in CDCl3 and DMSO-d6. This spectrum distinctly displayed the signals due to Ar-protons at δ 6.6098-8.4552 ppm, NH protons at δ 3.4693-3.4861 ppm, -CH proton at δ 2.5412-2.5499 ppm and –CH3 protons at δ 1.2433-1.3867 ppm 10)  Mass spectrum:-  The Mass analysis of the compound was carried out and the fragmentation occurs during the analysis is given in Mass Scheme-I. N NNN NNSM+1 = 243PVR 9 (363)N NNNCH3 NHNHC6H5SNHN NNSNH2M+ = 204N N+NNHNHC6H5NHN NNNCH3NHNHSNH2M+1 = 288  From the above properties and spectral analysis of the compound (IXa) was assigned the structure as 1-phenyl-2-phenylguanidino-4-methylimine-6-thio-1,3,5-triazine (IXa) IAJPS 2017, 4 (12), 4293-4300                          P. V. Raut et al                       ISSN 2349-7750    w w w . i a j p s . c o m   Page 4296 N NNH3C NCHSPhHN C NHPhNH1-Phenyl-2-phenylguanidino-4-methylimine-6-thio-1,3,5-triazine(IXa) Synthesis of 1-phenyl-2-phenylguanidino-4-phenylimine-6-thio-1,3,5-triazine (IXc): 2-Phenylguanidino-4-phenylimino-6-phenylimino-1,3,5-thiadiazine(VIIIc)  was suspended in 5% ethanolic sodium bicarbonate solution and refluxed for half an hour on water bath. During heating the reactant went into the solvent. After distillation of excess solvent milky white colour crystals were isolated. It was recrystallised from glacial acetic acid to obtain (IXc), yield 66%, m.p. 1310C. The probable reaction of the formation of (IXc) may be as depicted below (Scheme-VI).   N SNNCHN PhHN C NHPhNHPhN NNPh NCHSPhHN C NHPhNH2-Phenylguanidino-4-phenylimine-6-phenylimino-1,3,5-thiadiazineIsomerisation(VIIIc)1-Phenyl-2-phenylguanidino-4-phenylimine-6-thio-1,3,5-triazine(IXc) Reaction Scheme-3 Properties of (IXc): 1) It was milky white crystalline solid having m.p.1310C. 2) It gave positive test for nitrogen and sulphur. 3) It was desulphurized when boiled with alkaline plumbite solution. 4) It was soluble in benzene, acetic acid, dioxane, DMF and DMSO. 5) Elemental analysis: The result of elemental analysis is given in following table-3 Elements Found (%) Calculated (%) Carbon 63.95 64.94 Hydrogen 3.55 4.47 Nitrogen 23.05 23.05 Sulphur 6.51 7.52  7) From the analytical data the molecular formula was found to be C23H19N7S1. 8) IR Spectrum of compound: IR spectrum of compound was carried out in KBr pellets and the important absorptions are correlated as follows and are depicted in following table-4 Absorption observed in cm-1 Assignment Absorption Expected in cm-1 3389.8 NH stretching30 3500-3300 1636.7 N-C=N grouping showing hexocyclic ring31 1660-1500 1553.26 C=N stretching ring 1600-1430 1092.3 C-N stretching32 1200-1000 1405.19 C=S stretching33 1500-1200 668.29 Monosubstituted benzene 34 800-600 1510.16 Ar C=C stretching 1600-1475  IAJPS 2017, 4 (12), 4293-4300                          P. V. Raut et al                       ISSN 2349-7750    w w w . i a j p s . c o m   Page 4297 9) PMR-Spectrum: The PMR spectrum of compound was carried out in CDCl3 and DMSO-d6 and reproduced on PMR Plate No. PVR-10. This spectrum distinctly displayed the signals due to Ar-protons at δ 6.1380-7.9602 ppm, NH proton at δ 5.5986 ppm, =NH proton at δ 3.6594 ppm and -CH proton at δ 2.3946-2.5937 ppm.   From the above properties and spectral analysis of the compound (IXc) was assigned the structure as 1-phenyl-2-phenylguanidino-4-phenylimine-6-thio-1,3,5-triazine (IXc).  N NNPh NCHSPhHN C NHPhNH1-Phenyl-2-phenylguanidino-4-phenylimine-6-thio-1,3,5-triazine(IXc) Similarly, the other 2-phenylguanidino-4-ethylimino-6-phenylimino-1,3,5-thiadiazine (VIIIb), 2-phenylguanidino-4-(3-nitro)phenylimine-6-phenylimino-1,3,5-thiadiazine (VIIId), 2-phenylguanidino-4-(4-nitro)phenyl-imine-6-phenylimino-1,3,5-thiadiazine(VIIIe),  2-phenylguanidino-4-(3-p-di-methyl)-phenylimine-6-phenylimino-1,3,5-thiadiazine(VIIIf), 2-phenyl-guanidino-4-methylimino-6-ethylimino-1,3,5-thiadiazine(VIIIg), 2-phenyl-guanidino-4-ethylimino-6-ethylimino-1,3,5-thiadiazine (VIIIh), 2-phenyl-guanidino-4-phenylimino-6-ethylimino-1,3,5-thiadiazine (VIIIi), 2-phenyl-guanidino-4-(3-nitro)phenylimine-6-ethylimino-1,3,5-thiadiazine (VIIIj), 2-phenylguanidino-4-(4-nitro)phenylimine-6-ethylimino-1,3,5-thiadiazine (VIIIk),  2-phenylguanidino-4-(3-p-dimethyl)phenylimine-6-ethylimino-1,3,5-thiadiazine (VIIIl), 2-phenylguanidino-4-methylimino-6-(p-Cl)phenylimino-1,3,5-thiadi-azine (VIIIm), 2-phenylguanidino-4-ethylimino-6-(p-Cl)phenylimino-1,3,5-thiadiazine (VIIIn), 2-phenylguanidino-4-phenylimino-6-(p-Cl)phenylimino -1,3,5-thiadiazine (VIIIo), 2-phenylguanidino-4-(3-nitro)phenylimine-6-(p-Cl)-phenylimino-1,3,5-thiadiazine (VIIIp), 2-phenylguanidino-4-(4-nitro) phenyl-imine-6-(p-Cl)phenylimino -1,3,5-thiadiazine (VIIIq) and 2-phenyl guanidino-4-(3-p-dimethyl)phenylimine-6-(p-Cl)phenylimino-1,3,5-thiadiazine (VIIIr) were isomerises to  1-phenyl-2-phenylguanidino-4-ethylimine-6-thio-1,3,5-triazine (IXb), 1-phenyl-2-phenylguanidino-4-(3-nitro)phenylimine-6-thio-1,3,5-triazine (IXd), 1-phenyl-2-phenylguanidino-4-(4-nitro)phenylimine-6-thio-1,3,5-triazine (IXe),  1-phenyl-2-phenylguanidino-4-(p-dimethyl) phenylimine-6-thio-1,3,5-triazine (IXf), 1-ethyl-2-phenylguanidino-4-methylimine-6-thio-1,3,5-triazine (IXg), 1-ethyl-2-phenylguanidino-4-ethylimine-6-thio-1,3,5-triazine (IXh), 1-ethyl-2-phenylguanidino-4-phenylimine-6-thio-1,3,5-triazine (IXi)1-ethyl-2-phenylguanidino-4-(3-nitro)phenylimine-6-thio-1,3,5-triazine (IXj), 1-ethyl-2-phenylguanidino-4-(4-nitro)phenylimine-6-thio-1,3,5-triazine (IXk), 1-ethyl-2-phenylguanidino-4-(p-dimethyl)phenylimine-6-thio-1,3,5-triazine (IX l), 1-p-chlorophenyl-2-phenylguanidino-4-methylimine-6-thio-1,3,5-triazine(IXm), 1-p-chlorophenyl-2-phenylguanidino-4-ethylimine-6-thio-1,3,5-triazine (IXn), 1-p-chlorophenyl-2-phenylguanidino-4-phenylimine-6-thio-1,3,5-triazine (IXo), 1-p-chlorophenyl-2-phenylguanidino-4-(3-nitro)phenylimine-6-thio-1,3,5-tri-azine (IXp), 1-p-chlorophenyl-2-phenylguanidino-4-(4-nitro)phenylimine-6-thio-1,3,5-triazine (IXq) and  1-p-chlorophenyl-2-phenyl guanidino-4-(p-di-methyl)phenylimine-6-thio-1,3,5-triazine (IXr) respectively by above mentioned method and described in Experiment No. 1-18 and enlisted in following table-5.            IAJPS 2017, 4 (12), 4293-4300                          P. V. Raut et al                       ISSN 2349-7750    w w w . i a j p s . c o m   Page 4298  Sr.No. 2-Substituted guanidine -4-substitutedimino-1,3,5-thiadiazines (VIIIa-r) 1-Substituted-2-substitutedguanidino-4-substitutedimine-6-thio-1,3,5-triazines (IXa-r) Yield (%) m.p. (0C)    1     2    3       4    5    6      7     8    9      10    11       2-phenylguanidino-4-ethylimino-6-phenylimino-1,3,5-thiadiazine(VIIIb)  2-phenylguanidino-4-(3-nitro)phenylimine-6-phenylimino -1,3,5-thiadiazine (VIIId)  2-phenylguanidino-4-(4-nitro)phenylimine-6-phenylimino-1,3,5-thiadiazine(VIIIe)   2-phenylguanidino-4-(3-p-dimethyl)- phenylimine-6-phenylimino-1,3,5-thiadiazine(VIIIf)  2-phenylguanidino-4-methylimino-6-ethylimino-1,3,5-thiadiazine(VIIIg)  2-phenylguanidino-4-ethylimino-6-ethylimino-1,3,5-thiadiazine (VIIIh)   2-phenylguanidino-4-phenylimino-6-ethylimino-1,3,5-thiadiazine (VIIIi)   2-phenylguanidino-4-(3-nitro)phenylimine-6-ethylimino-1,3,5-thiadiazine (VIIIj)  2-phenylguanidino-4-(4-nitro)phenylimine-6-ethylimino-1,3,5-thiadiazine (VIIIk)  2-phenyl guanidino-4-(3-p-dimethyl)phenylimine-6-ethylimino-1,3,5-thiadiazine (VIII l)  2-phenylguanidino-4-methylimino-6-(p-Cl)phenylimino-1,3,5-thiadiazine (VIIIm)    1-phenyl-2-phenylguanidino-4-ethylimine-6-thio-1,3,5-triazine (IXb)  1-phenyl-2-phenylguanidino-4-(3-nitro)phenylimine-6-thio-1,3,5-triazine (IXd)   1-phenyl-2-phenylguanidino-4-(4-nitro)phenylimine-6-thio-1,3,5-triazine (IXe)    1-phenyl-2-phenylguanidino-4-(p-dimethyl) phenyl imine-6-thio-1,3,5-triazine (IXf)   1-ethyl-2-phenylguanidino-4-methylimine-6-thio-1,3,5-triazine (IXg)  1-ethyl-2-phenylguanidino-4-ethylimine-6-thio-1,3,5-triazine (IXh)   1-ethyl-2-phenylguanidino-4-phenylimine-6-thio-1,3,5-triazine (IXi)   1-ethyl-2-phenylguanidino-4-(3-nitro)phenylimine-6-thio-1,3,5-triazine (IXj)   1-ethyl-2-phenylguanidino-4-(4-nitro)phenylimine-6-thio-1,3,5-triazine (IXk)   1-ethyl-2-phenylguanidino-4-(p-dimethyl)phenylimine-6-thio-1,3,5-triazine (IX l)  1-p-chlorophenyl-2-phenylguanidino-4-methylimine-6-thio-1,3,5-triazine (IXm)     74     78     73      68     70    73     75     68     72     69    64        115    119     130      123     127    124     116     113     117     129    145       IAJPS 2017, 4 (12), 4293-4300                          P. V. Raut et al                       ISSN 2349-7750    w w w . i a j p s . c o m   Page 4299 12      13      14      15    16     2-phenylguanidino-4-ethylimino-6-(p-Cl)phenylimino-1,3,5-thiadiazine (VIIIn)   2-phenylguanidino-4-phenylimino-6-(p-Cl)phenylimino -1,3,5-thiadiazine (VIIIo)   2-phenylguanidino-4-(3-nitro)phenylimine-6-(p-Cl)phenylimino -1,3,5-thiadiazine (VIIIp)  2-phenylguanidino-4-(4-nitro) phenylimine-6-(p-Cl)phenylimino -1,3,5-thiadiazine (VIIIq)  2-phenyl guanidino-4-(3-p-dimethyl)phenylimine-6-(p-Cl)phenylimino-1,3,5-thiadiazine (VIIIr)  1-p-chlorophenyl-2-phenylguanidino-4-ethylimine-6-thio-1,3,5-triazine (IXn)   1-p-chlorophenyl-2-phenylguanidino-4-phenylimine-6-thio-1,3,5-triazine (IXo)   1-p-chlorophenyl-2-phenylguanidino-4-(3-nitro) phenylimine-6-thio-1,3,5-triazine (IXp)  1-p-chlorophenyl-2-phenylguanidino-4-(4-nitro)phenylimine-6-thio-1,3,5-triazine (IXq)  1-p-chlorophenyl-2-phenyl guanidino-4-(p-dimethyl)phenylimine-6-thio-1,3,5-triazine (IX r)  66       70      64     68     75    127       125      135    128      119     CONCLUSION: Data obtained by the chemical tests, elemental analysis & spectral characterization strongly supports the target molecules.  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SYNTHESIS OF 1-SUBSTITUTED-2-SUBSTITUTEDGUANIDINO-4-SUBSTITUTEDIMINE-6-THIO-1,3,5-TRIAZINES

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SYNTHESIS OF 1-SUBSTITUTED-2-SUBSTITUTEDGUANIDINO-4-SUBSTITUTEDIMINE-6-THIO-1,3,5-TRIAZINES

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