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How to cite this paper
APA: Pansare, D., Shelke, R., Pawar, C., Sarkate, A., Chavan, P., Thopate, S & Shinde, D. (2019). Green synthesis of 4-methoxybenzylidene thiazole derivatives using potassium carbonate as base under ultrasound irradiation. Current Chemistry Letters, 8(4), 211-224.
Chicago/Turabian: Pansare, D., Shelke, R., Pawar, C., Sarkate, A., Chavan, P., Thopate, S & Shinde, D. 2019. "Green synthesis of 4-methoxybenzylidene thiazole derivatives using potassium carbonate as base under ultrasound irradiation." Current Chemistry Letters 8, no. 4 (2019): 211-224.
AMA: Pansare, D., Shelke, R., Pawar, C., Sarkate, A., Chavan, P., Thopate, S & Shinde, D. Green synthesis of 4-methoxybenzylidene thiazole derivatives using potassium carbonate as base under ultrasound irradiation. Current Chemistry Letters. 2019;8(4):211-224.
References
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22. Jin X., Zheng C. J., Song M. X., Wu Y., Sun L. P., Li Y. J., Yu L. J., Piao H. R., (2012) Synthesis and antimicrobial evaluation of L-phenylalanine-derived C5-substituted rhodanine and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone. Eur. J. Med. Chem. 56, 203–209.
23. Coulibaly W. K., Paquin L., Benie A., Bekro Y. A., Durieux E., Meijer L., Guevel R. L., Corlu A., Bazureau J. P. (2012) Synthesis of New N,N'-Bis(5-arylidene-4-oxo-4,5-dihydrothiazolin-2-yl)piperazine Derivatives Under Microwave Irradiation and Preliminary Biological Evaluation. Sci. Pharm. 80, 825–836.
24. Kaminskyy D., Khyluk D., Vasylenko O., Lesyk R. (2012) An Efficient Method for the Transformation of 5-Ylidenerhodanines into 2,3,5-Trisubstituted-4-thiazolidinones. Tetrahedron Lett. 53, 557–559.
25. Guernon J. M., Wu Y. J. (2011) 3-Bromocyclohexane-1,2-dione as a useful reagent for Hantzsch synthesis of thiazoles and the synthesis of related heterocycles. Tetrahedron Lett. 52, 3633–3635.
26. Khaligh N.G., Shirini F. (2014) Ultrasound assisted the chemoselective 1,1-diacetate protection and deprotection of aldehydes catalyzed by poly(4-vinylpyridinium)hydrogen sulfate salt as a eco-benign, efficient and reusable solid acid base. Ultrason. Sonochem. 20, 19–25.
27. Li J.T., Yin Y., Li L., Sun M. X. (2010) A convenient and efficient protocol for the synthesis of 5-aryl-1,3-diphenylpyrazole catalyzed by hydrochloric acid under ultrasound irradiation. Ultrason. Sonochem. 17, 11–13.
28. Srivastava R. M., Filho R. A., Silva C. A., Bortoluzzi A. (2009) First ultrasound-mediated one-pot synthesis of N-substituted amides. Ultrason. Sonochem. 16, 737–742.
29. Prasad K., Pinjari D. V., Pandit A.B., Mhaske S. T. (2010) Phase transformation of nanostructured titanium dioxide from anatase-to-rutile via combined ultrasound assisted sol-gel technique. Ultrason. Sonochem. 17, 409– 415.
30. Jarag K. J., Pinjari D. V., Pandit A. B., Shankarling G.S. (2011) Synthesis of chalcone (3-(4-fluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one): advantage of sonochemical method over conventional method. Ultrason. Sonochem. 18, 617–623.
31. Fu L. H., Dong Y. Y., Ma M. G., Li S. M., Sun R. C. (2014) Compare study CaCO3 crystals on the cellulose substrate by microwave-assisted method and ultrasound agitation method. Ultrason. Sonochem. 20, 839–845.
32. Suslick K. S., Choe S. B., Cichowlas A. A., Grinstaff M. W. (1991) Sonochemical synthesis of amorphous iron. Nature 353, 414–416.
33. Bretanha L. C., Teixeira V. E., Ritter M., Siqueira G. M., Cunico W., Pereira C. M. P., Freitag R. A. (2007) Ultrasound-promoted synthesis of 3-trichloromethyl-5-alkyl(aryl)-1,2,4-oxadiazoles. Ultrason. Sonochem. 18, 704–707.
34. Duarte A., Cunico W., Pereira C. M. P., Flores A. F. C., Freitag R. A., Siqueira G. M. (2010) Ultrasound promoted synthesis of thioesters from 2-mercaptobenzoxa(thia)zoles. Ultrason. Sonochem. 17, 281–283.
35. Lorimer J. P., Mason T. J. (1987) sonochemistry part 1- The physical aspects, Chem. Soc. Rev. 16, 239–274.
36. Pansare D. N., Shelke R. N., Pawar C. D. (2017) A facile synthesis of (Z)-2-((5-(4-chlorobenzylidene)-4-oxo-4,5-dihydrothiazol-2-yl)amino)substituted acid using microwave irradiation and conventional method. Lett. Org. Chem. 14(7), 517-524.
37. Pansare D. N., Shelke R. N., Shinde D. B. (2017) A facial synthesis and anticancer activity of (Z)-2-((5-(4-nitrobenzylidene) -4-oxo-4,5-dihydrothiazol-2-yl)amino) substituted acid. J. Het. Chem. 54(6), 3077–3086.
38. Pansare D. N., Shinde D. B. (2017) A facile synthesis of novel series (Z)-2-((4-oxo-5-(thiophen-2-yl methylene)-4,5-dihydro thiazol-2-yl)amino) substituted acid. J. Saudi. Chem. Soc. 21, 434-440.
39. Pansare D. N., Shinde D. B. (2015) Synthesis and Antimicrobial Activity of new (Z)-2-((5-(4-Hydroxybenzylidene)-4-Oxo-4,5-Dihydrothiazol-2-Yl)Amino) Acid and its Derivatives. Res. Rev. J. Chem. 4(1), 1-7.
40. Pawar C. D., Chavan, S. L., Pawar U. D., Pansare D. N., Deshmukh S. V., Shinde D. B. (2018) Synthesis, anti-proliferative activity, SAR and Kinase inhibition studies of thiazol-2-yl- substituted sulfonamide derivatives. J. Chin. Chem. Soc. DOI- 10.1002/jccs.201800312
41. Pawar C. D., Pansare D. N., Shinde D. B. (2018) (Substituted)-benzo[b]thiophene-4-carboxamide synthesis and anti-proliferative activity study. Lett. Drug. Des. Disc. DOI- 10.2174/1570180815666181004114125
42. Pawar C. D., Pansare D. N., Shinde D. B. (2018) Synthesis of new 3-(substituted phenyl)-N-(2-hydroxy-2-(substituted phenyl)ethyl)-N-methylthiophene-2-sulfonamide derivatives as antiproliferative agents. Eur. J. Chem. 9(1), 13-21.
43. Pawar C. D., Pansare D. N., Shinde D. B., (2017) Synthesis and antiproliferative activity of 3-(substituted)-4,5,6,7-tetrahydro-6-(substituted)-1H-pyrazolo[3,4-c]pyridine Derivatives. Eur. J. Chem. 8(4). 400‐409.
44. Pawar C. D., Sarkate A. P., Karnik K. S., Bahekar S. S., Pansare D. N., Shelke R. N., Jawale C. S., Shinde D. B. (2016) Synthesis and antimicrobial evaluation of novel ethyl 2-(2-(4-substituted) acetamido)-4-subtituted-thiazole-5-carboxylate derivatives. Bioorg. Med. Chem. Lett., 26, 3525-3528.
45. Pawar C. D., Sarkate A. P., Karnik K. S., Pansare D. N., Shinde D. B. (2017) Synthesis and antiproliferative evaluation of new (4-substituted-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methane substituted sulfonamide derivatives. Eur. J. Chem. 8, 384 - 390.
46. Sarkate A. P., Pansare D. N., Kale I., Bahekar S. S., Shinde D. B. (2017) Microwave assisted copper-catalyzed synthesis of substituted benzamides through decarboxylative C-N cross coupling. Curr. Micro. Chem. 4, 163-167
47. Sarkate A. P., Pansare D. N., Kale I, Shinde D. B. (2017) Microwave and Conventional Method Assisted Synthesis of 2-(substituted) -3-(4-methoxybenzyl) Thiazolidin-4-ones Using ZrOCl2•8H2O as a Base. Curr. Micro. Chem. 4(2), 139-145.
48. Shelke R. N., Pansare D. N., Pawar C. D., Pawar R. P., Bembalkar S. R. (2017) Synthesis of 3H‐imidazo[4,5‐b] pyridine with evaluation of their anticancer and antimicrobial activity. Eur. J. Chem. 8(1), 25‐32.
2. Carradori S., Secci D., Bolasco A., De Monte C., Yanez M. (2012) Synthesis and selective inhibitory activity against human COX-1 of novel 1-(4-substituted-thiazol-2-yl)-3,5-di(hetero)aryl-pyrazoline derivatives. Arch. Pharm. 345, 973–979.
3. Holla B.S., Malini K.V., Rao B.S., Sarojini B.K., Kumari N.S. (2003) Synthesis of some new 2,4-disubstituted thiazoles as possible antibacterial and anti-inflammatory agents. Eur. J. Med. Chem. 38, 313–318.
4. Toyoshi K., Misako A., Masako K., Katsuya O., Shigekatsu K., Tamatsu M., Takeshi I. (1985) Syntheses and Antiinflammatory Activity of Malonamic Acid, Malonamate and Malonamide Derivatives of Some Heterocyclic Compounds. Chem. Pharm. Bull. 33, 4878–4888.
5. Murugan R., Anbazhagan S., Lingeshwaran S., Narayanan S., (2009) Corrigendum to “Synthesis and in vivo antidiabetic activity of novel dispiropyrrolidines through [3+2] cycloaddition reactions with thiazolidinedione and rhodanine derivatives. Eur. J. Med. Chem. 44, 3272–3279.
6. Chandrappa S., Kavitha C.V., Shahabuddin M. S., Vinaya K., Ananda C. S., Ranganatha S. R., Raghavan S. C., Rangappa K. S. (2009) Synthesis of 2-(5-((5-(4-chlorophenyl)furan-2-yl) methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid derivatives and evaluation of their cytotoxicity and induction of apoptosis in human leukemia cells. Bioorg. Med. Chem. 17, 2576–2584.
7. Brooke E. W., Davies S. G., Mulvaney A.W., Okada M., Pompeo F., Sim E., Vickers R. J., Westwood I. M. (2003) Synthesis and in vitro evaluation of novel small molecule inhibitors of bacterial arylamine N-acetyltransferases (NATs). Bioorg. Med. Chem. 13, 2527–2530.
8. Mallikarjuna B. P., Sastry B. S., Suresh G. V., Rajendra prasad Y., Chandrashekar S. M., Sathisha K. (2009) Synthesis of new 4-isopropylthiazole hydrazide analogs and some derived clubbed triazole, oxadiazole ring systems--a novel class of potential antibacterial, antifungal and antitubercular agents. Eur. J. Med. Chem. 44, 4739–4746.
9. Balzarini J., Orzeszko B., Maurin J. K., Orzeszko A. (2007) Synthesis and anti-HIV studies of 2-adamantyl-substituted thiazolidin-4-ones. Eur. J. Med. Chem. 42, 993–1003.
10. Murugesan V., Tiwari V.S., Saxena R., Tripathi R., Paranjape R., Kulkarni S., Makwana N., Suryawanshi R., Katti S. B. (2011) Lead optimization at C-2 and N-3 positions of thiazolidin-4-ones as HIV-1 non-nucleoside reverse transcriptase inhibitors. Bioorg. Med. Chem. 19, 6919–6926.
11. Rawal R. K., Tripathi R., Katti S. B., Pannecouque C., Clercq E. D. (2007) Synthesis and evaluation of 2-(2,6-dihalophenyl)-3-pyrimidinyl-1,3-thiazolidin-4-one analogues as anti-HIV-1 agents. Bioorg. Med. Chem. 15, 3134–3142.
12. Zhang X., Li X., Li D., Qua G., Wang J., Loiseau P. M., Fan X. (2009) Ionic Liquid Mediated and Promoted Eco-Friendly Preparation of Thiazolidinone and Pyrimidine Nucleoside-Thiazolidinone Hybridsand Their Antiparasitic Activities. Bioorg. Med. Chem. Lett. 19, 6280–6283.
13. Verma A., Saraf S. K. (2008) 4-thiazolidinone-A biologically active scaffold. Eur. J. Med. Chem. 43, 897–905.
14. Gouveia F. L., de Oliveira R. M. B., de Oliveira T. B., da Silva I.M., do Nascimento S. C., de Sena K. X. F. R., de Albuquerque J. F. C. (2009) Synthesis, antimicrobial and cytotoxic activities of some 5-arylidene-4-thioxo-thiazolidine-2-ones. Eur. J. Med. Chem. 44, 2038–2043.
15. Ottana R., Carotti S., Maccari R., Landini I., Chiricosta G., Caciagli B., Vigorita M. G., Mini E., (2005) In vitro antiproliferative activity against human colon cancer cell lines of representative 4-thiazolidinones. Part I. Bioorg. Med. Chem. Lett. 15, 3930–3933.
16. Shah T. J., Desai V. A. (2007) Synthesis of some novel fluorinated 4-thiazolidinones containing
17. amide linkages and their antimicrobial screening. ARKIVOC, 14, 218–228.
18. Gualtieri M., Bastide L., Latouche P. V., Leonette J. P. (2006) In-vitro activity of a new antibacterial rhodanine derivative against Staphylococcus epidermidis biofilms. J. Antimicrob. Chemother. 58, 778–783.
19. Sim M. M., Ng S. B., Buss A. D., Crasta S. C., Goh K. L., Lee S. K. (2002) Benzylidene rhodanines as novel inhibitors of UDP-N-acetylmuramate/l-alanine ligase. Bioorg. Med. Chem. Lett. 12, 697–699.
20. Petrikaite V., Tarasevicius E., Pavilonis A. (2007) New ethacridine derivatives as the potential antifungal and antibacterial preparations. Medicina (Kaunas) 43, 657–663.
21. Sortino M., Delgado P., Juarez S., Quiroga J., Abonia R., Insuasty B., Nogueras M., Rodero L., Garibotto F. M., Enriz R. D., Zacchino S. A. (2007) Synthesis and antifungal activity of (Z)-5-arylidenerhodanines. Bioorg. Med. Chem. 15, 484–494.
22. Jin X., Zheng C. J., Song M. X., Wu Y., Sun L. P., Li Y. J., Yu L. J., Piao H. R., (2012) Synthesis and antimicrobial evaluation of L-phenylalanine-derived C5-substituted rhodanine and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone. Eur. J. Med. Chem. 56, 203–209.
23. Coulibaly W. K., Paquin L., Benie A., Bekro Y. A., Durieux E., Meijer L., Guevel R. L., Corlu A., Bazureau J. P. (2012) Synthesis of New N,N'-Bis(5-arylidene-4-oxo-4,5-dihydrothiazolin-2-yl)piperazine Derivatives Under Microwave Irradiation and Preliminary Biological Evaluation. Sci. Pharm. 80, 825–836.
24. Kaminskyy D., Khyluk D., Vasylenko O., Lesyk R. (2012) An Efficient Method for the Transformation of 5-Ylidenerhodanines into 2,3,5-Trisubstituted-4-thiazolidinones. Tetrahedron Lett. 53, 557–559.
25. Guernon J. M., Wu Y. J. (2011) 3-Bromocyclohexane-1,2-dione as a useful reagent for Hantzsch synthesis of thiazoles and the synthesis of related heterocycles. Tetrahedron Lett. 52, 3633–3635.
26. Khaligh N.G., Shirini F. (2014) Ultrasound assisted the chemoselective 1,1-diacetate protection and deprotection of aldehydes catalyzed by poly(4-vinylpyridinium)hydrogen sulfate salt as a eco-benign, efficient and reusable solid acid base. Ultrason. Sonochem. 20, 19–25.
27. Li J.T., Yin Y., Li L., Sun M. X. (2010) A convenient and efficient protocol for the synthesis of 5-aryl-1,3-diphenylpyrazole catalyzed by hydrochloric acid under ultrasound irradiation. Ultrason. Sonochem. 17, 11–13.
28. Srivastava R. M., Filho R. A., Silva C. A., Bortoluzzi A. (2009) First ultrasound-mediated one-pot synthesis of N-substituted amides. Ultrason. Sonochem. 16, 737–742.
29. Prasad K., Pinjari D. V., Pandit A.B., Mhaske S. T. (2010) Phase transformation of nanostructured titanium dioxide from anatase-to-rutile via combined ultrasound assisted sol-gel technique. Ultrason. Sonochem. 17, 409– 415.
30. Jarag K. J., Pinjari D. V., Pandit A. B., Shankarling G.S. (2011) Synthesis of chalcone (3-(4-fluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one): advantage of sonochemical method over conventional method. Ultrason. Sonochem. 18, 617–623.
31. Fu L. H., Dong Y. Y., Ma M. G., Li S. M., Sun R. C. (2014) Compare study CaCO3 crystals on the cellulose substrate by microwave-assisted method and ultrasound agitation method. Ultrason. Sonochem. 20, 839–845.
32. Suslick K. S., Choe S. B., Cichowlas A. A., Grinstaff M. W. (1991) Sonochemical synthesis of amorphous iron. Nature 353, 414–416.
33. Bretanha L. C., Teixeira V. E., Ritter M., Siqueira G. M., Cunico W., Pereira C. M. P., Freitag R. A. (2007) Ultrasound-promoted synthesis of 3-trichloromethyl-5-alkyl(aryl)-1,2,4-oxadiazoles. Ultrason. Sonochem. 18, 704–707.
34. Duarte A., Cunico W., Pereira C. M. P., Flores A. F. C., Freitag R. A., Siqueira G. M. (2010) Ultrasound promoted synthesis of thioesters from 2-mercaptobenzoxa(thia)zoles. Ultrason. Sonochem. 17, 281–283.
35. Lorimer J. P., Mason T. J. (1987) sonochemistry part 1- The physical aspects, Chem. Soc. Rev. 16, 239–274.
36. Pansare D. N., Shelke R. N., Pawar C. D. (2017) A facile synthesis of (Z)-2-((5-(4-chlorobenzylidene)-4-oxo-4,5-dihydrothiazol-2-yl)amino)substituted acid using microwave irradiation and conventional method. Lett. Org. Chem. 14(7), 517-524.
37. Pansare D. N., Shelke R. N., Shinde D. B. (2017) A facial synthesis and anticancer activity of (Z)-2-((5-(4-nitrobenzylidene) -4-oxo-4,5-dihydrothiazol-2-yl)amino) substituted acid. J. Het. Chem. 54(6), 3077–3086.
38. Pansare D. N., Shinde D. B. (2017) A facile synthesis of novel series (Z)-2-((4-oxo-5-(thiophen-2-yl methylene)-4,5-dihydro thiazol-2-yl)amino) substituted acid. J. Saudi. Chem. Soc. 21, 434-440.
39. Pansare D. N., Shinde D. B. (2015) Synthesis and Antimicrobial Activity of new (Z)-2-((5-(4-Hydroxybenzylidene)-4-Oxo-4,5-Dihydrothiazol-2-Yl)Amino) Acid and its Derivatives. Res. Rev. J. Chem. 4(1), 1-7.
40. Pawar C. D., Chavan, S. L., Pawar U. D., Pansare D. N., Deshmukh S. V., Shinde D. B. (2018) Synthesis, anti-proliferative activity, SAR and Kinase inhibition studies of thiazol-2-yl- substituted sulfonamide derivatives. J. Chin. Chem. Soc. DOI- 10.1002/jccs.201800312
41. Pawar C. D., Pansare D. N., Shinde D. B. (2018) (Substituted)-benzo[b]thiophene-4-carboxamide synthesis and anti-proliferative activity study. Lett. Drug. Des. Disc. DOI- 10.2174/1570180815666181004114125
42. Pawar C. D., Pansare D. N., Shinde D. B. (2018) Synthesis of new 3-(substituted phenyl)-N-(2-hydroxy-2-(substituted phenyl)ethyl)-N-methylthiophene-2-sulfonamide derivatives as antiproliferative agents. Eur. J. Chem. 9(1), 13-21.
43. Pawar C. D., Pansare D. N., Shinde D. B., (2017) Synthesis and antiproliferative activity of 3-(substituted)-4,5,6,7-tetrahydro-6-(substituted)-1H-pyrazolo[3,4-c]pyridine Derivatives. Eur. J. Chem. 8(4). 400‐409.
44. Pawar C. D., Sarkate A. P., Karnik K. S., Bahekar S. S., Pansare D. N., Shelke R. N., Jawale C. S., Shinde D. B. (2016) Synthesis and antimicrobial evaluation of novel ethyl 2-(2-(4-substituted) acetamido)-4-subtituted-thiazole-5-carboxylate derivatives. Bioorg. Med. Chem. Lett., 26, 3525-3528.
45. Pawar C. D., Sarkate A. P., Karnik K. S., Pansare D. N., Shinde D. B. (2017) Synthesis and antiproliferative evaluation of new (4-substituted-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methane substituted sulfonamide derivatives. Eur. J. Chem. 8, 384 - 390.
46. Sarkate A. P., Pansare D. N., Kale I., Bahekar S. S., Shinde D. B. (2017) Microwave assisted copper-catalyzed synthesis of substituted benzamides through decarboxylative C-N cross coupling. Curr. Micro. Chem. 4, 163-167
47. Sarkate A. P., Pansare D. N., Kale I, Shinde D. B. (2017) Microwave and Conventional Method Assisted Synthesis of 2-(substituted) -3-(4-methoxybenzyl) Thiazolidin-4-ones Using ZrOCl2•8H2O as a Base. Curr. Micro. Chem. 4(2), 139-145.
48. Shelke R. N., Pansare D. N., Pawar C. D., Pawar R. P., Bembalkar S. R. (2017) Synthesis of 3H‐imidazo[4,5‐b] pyridine with evaluation of their anticancer and antimicrobial activity. Eur. J. Chem. 8(1), 25‐32.