Trimethylsilyl Chloride Catalyzed Highly Efficient Synthesis of Schiff Bases of Thiazole in Glycerol under Microwave Irradiation

Mujahed Shaikh; Ashvini Sonone; Mazahar Farooqui; Ayesha Durrani

doi:10.14233/ajomc.2019.AJOMC-P170

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Abstract

A green and environmentally benign protocol is developed for the synthesis of Schiff bases of sulphur containing compound by irradiating thiazole and pyrazole aldehyde in glycerol under microwave irradiation at 70 ºC with trimethylsilyl chloride (TMSCl) as a catalyst. The method has advantages such as excellent yield, use of green solvent, easy work-up and most important the reaction completed within 2.5 min by using TMSCl catalyst. The TMSCl is an acidic catalyst, which enhances the yield of product, reaction time (with microwave, with reflux at 75 ºC and with stirring at room temperature) which can be easily removed from reaction mask.

Keywords

Trimethylsilyl chloride Pyrazole aldehyde 2-Aminothaizole Schiff bases Glycerol

How to Cite

Shaikh, M., Sonone, A., Farooqui, M., & Durrani, A. (2019). Trimethylsilyl Chloride Catalyzed Highly Efficient Synthesis of Schiff Bases of Thiazole in Glycerol under Microwave Irradiation. Asian Journal of Organic & Medicinal Chemistry, 4(2), 109–112. https://doi.org/10.14233/ajomc.2019.AJOMC-P170

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References

G. Beck and H. Heitzer, Preparation of 2-Chloro-5-Chloromethylthiazole, US Patent 4,7482,43A (1988).
F.W. Bell, A.S. Cantrell, M. Hoegberg, S.R. Jaskunas, N.G. Johansson, C.L. Jordan, M.D. Kinnick, P. Lind and J.M. Morin, Phenethylthiazole-thiourea (PETT) Compounds, A New Class of HIV-1 Reverse Transcrip-tase Inhibitors. 1. Synthesis and Basic Structure-Activity Relationship Studies of PETT Analogs, J. Med. Chem., 38, 4929 (1995); https://doi.org/10.1021/jm00025a010.
W.C. Patt, H.W. Hamilton, M.D. Taylor, M.J. Ryan, D.G. Taylor, C.J.C. Connolly, A.M. Doherty, S.R. Klutchko and I. Sircar, Structure-Activity Relationships of a Series of 2-Amino-4-thiazole containing Renin Inhibitors, J. Med. Chem., 35, 2562 (1992); https://doi.org/10.1021/jm00092a006.
T.K. Venkatachalam, E.A. Sudbeck, C. Mao and F.M. Uckun, Anti-HIV Activity of Aromatic and Heterocyclic Thiazolyl Thiourea compounds, Bioorg. Med. Chem. Lett., 11, 523 (2001); https://doi.org/10.1016/S0960-894X(01)00011-7.
F. Clemence, O. Le Martret, F. Delevallee, J. Benzoni, A. Jouanen, S. Jouquey, M. Mouren and R. Deraedt, 4-Hydroxy-3-quinolinecarboxamides with Antiarthritic and Analgesic Activities, J. Med. Chem., 31, 1453 (1988); https://doi.org/10.1021/jm00402a034.
K. Tsuji and H. Ishikawa, Synthesis and Anti-Pseudomonal Activity of New 2-Isocephems with a Dihydroxypyridone Moiety at C-7, Bioorg. Med. Chem. Lett., 4, 1601 (1994); https://doi.org/10.1016/S0960-894X(01)80574-6.
M.C. Wilkes, P.B. Lavrik and J. Greenplate, Synthesis of N-Benzoyl-N-alkyl-2-aminothiazoles: Heliothis virescens Proinsecticides, J. Agric. Food Chem., 39, 1652 (1991); https://doi.org/10.1021/jf00009a023.
N. Vukovic, S. Sukdolak, S. Solujic and T. Milosevic, Synthesis and Antimicrobial Evaluation of Some Novel 2-Aminothiazole Derivatives of 4-Hydroxychromene-2-one, Arch. Pharm., 341, 491 (2008); https://doi.org/10.1002/ardp.200700215.
H.L. Chang, H.L. Lin, Y.C. Wang, S.A. Dai, W.C. Su and R.J. Jeng, Thermally Stable NLO Poly(amide-imide)s via Sequential Self-Repetitive Reaction, Polymer, 48, 2046 (2007); https://doi.org/10.1016/j.polymer.2007.02.010.
T. Baehr-Jones, M. Hochberg, G. Wang, R. Lawson, Y. Liao, P.A. Sullivan, L. Dalton, A.K.-Y. Jen and A. Scherer, Optical Modulation and Detection in Slotted Silicon Waveguides, Opt. Express, 13, 5216 (2005); https://doi.org/10.1364/OPEX.13.005216.
Y. Cui, H. Ren, J. Yu, Z. Wang and G. Qian, An Indanone-Based Alkoxy-silane Dye with Second Order Nonlinear Optical Properties, Dyes Pigments, 81, 53 (2009); https://doi.org/10.1016/j.dyepig.2008.09.002.
F. Qiu, Y. Zhou, J. Liu and X. Zhang, Preparation, Morphological and Thermal Stability of Polyimide/Silica Hybrid Material Containing Dye NBDPA, Dyes Pigments, 71, 37 (2006); https://doi.org/10.1016/j.dyepig.2005.05.009.
P.L. Lobo, B. Poojary, M. Kumsi, V. Chandra, N.S. Kumari and K.R. Chandrashekar, Synthesis, Antimicrobial and Antioxidant Activities of 2-[1-{3,5-Diaryl-4,5-dihydro-1H-pyrazolenyl}]-4-(4-nitrophenyl)-[1,3]thiazoles, Med. Chem. Res., 22, 1689 (2013); https://doi.org/10.1007/s00044-012-0154-3.
K. Hazra, L.V.G. Nargund, P. Rashmi, J.N.N. Sharath Chandra and B. Nandha, Synthesis and Antioxidant Activity of Some Novel Fluorobenzo-thiazolopyrazoline, Der Chem. Sinica, 2, 149 (2011).
B.P. Bandgar, S.S. Gawande, R.G. Bodade, N.M. Gawande and C.N. Khobragade, Synthesis and Biological Evaluation of a Novel Series of Pyrazole Chalcones as Anti-Inflammatory, Antioxidant and Antimicro-bial Agents, Bioorg. Med. Chem., 17, 8168 (2009); https://doi.org/10.1016/j.bmc.2009.10.035.
A.M. Youssef, M.S. White, E.B. Villanueva, I.M. El-Ashmawy and A. Klegeris, Synthesis and Biological Evaluation of Novel Pyrazolyl-2,4-thiazolidinediones as Anti-Inflammatory and Neuroprotective Agents, Bioorg. Med. Chem., 18, 2019 (2010); https://doi.org/10.1016/j.bmc.2010.01.021.
R.Verma, P. Chawla and S.K. Saraf, Syntheses, Characterization and Evaluation of Some 1,3,4-Trisubstituted-5-pyrazolone Derivatives as Dual Anti-Inflammatory and Antimicrobial Agents, Der Pharm. Sinica, 3, 546 (2012).
P.N. Balaji, L.K. Lakshmi, K. Mohan, K. Revathi, A. Chamundeswari and P.M. Indrani, In-vitro Anti-Inflammatory and Antimicrobial Activity of Synthesized Some Novel Pyrazole Derivatives from Coumarin Chalcones, Der Pharm. Sinica, 3, 685 (2012).
A. Özdemir, G. Turan-Zitouni, Z. Asim Kaplancikli, G. Revial and K. Güven, Synthesis and Antimicrobial Activity of 1-(4-Aryl-2-thiazolyl)-3-(2-thienyl)-5-aryl-2-pyrazoline Derivatives, Eur. J. Med. Chem., 42, 403 (2007); https://doi.org/10.1016/j.ejmech.2006.10.001.
Ch.S. Reddy, M.V. Devi, G.R. Kumar, L.S. Rao and A. Nagaraj, Synthesis and Antimicrobial Activity of Linked Heterocyclics Containing Pyrazole-Pyrimidine Rings, Indian J. Chem., 50B, 1181 (2011).
P. Patel, D. Gor and P.S. Patel, Synthesis, Characterization and Anti-microbial Activities of N-[{4-[2-{3,5-bis(4-Methoxyphenyl)-4,5-dihydro-pyrazol-yl}-2-oxoethoxy]phenyl}methylene] Substituted Aniline, Der Chem. Sinica, 3, 896 (2012).
S. Kumar, G. Kumar, M. Kapoor, A. Surolia and N. Surolia, Synthesis and Evaluation of Substituted Pyrazoles: Potential Antimalarials Targeting the Enoyl-ACP Reductase of Plasmodium Falciparum, Synth. Commun., 36, 215 (2006); https://doi.org/10.1080/00397910500334561.
S. Chandrasekhar, C. Narsihmulu, G. Chandrashekar and T. Shyamsunder, Pd/CaCO3 in Liquid Poly(ethylene glycol) (PEG): An Easy and Efficient Recycle System for Partial Reduction of Alkynes to cis-Olefins under a Hydrogen Atmosphere, Tetrahedron Lett., 45, 2421 (2004); https://doi.org/10.1016/j.tetlet.2004.01.097.
M.H. Shaikh, D.S. Wagare, M. Farooqui and A. Durrani, Facile and Green One-Pot Synthesis of 2-aminothiazoles in Glycerol-Water, Heterocycl. Lett., 7, 1061 (2017).
D.S. Wagare, P.D. Netankar, M. Shaikh, M. Farooqui and A. Durrani, Highly Efficient Microwave-Assisted One-Pot Synthesis of 4-Aryl-2-amino-thiazoles in Aqueous Medium, Environ. Chem. Lett., 15, 475 (2016); https://doi.org/10.1007/s10311-017-0619-1.
V. Ravibabu, B. Janardhan, G. Rajitha and B. Rajitha, Efficient One-Pot Three-component Synthesis of Thiazolyl Pyrazole Derivatives under Conventional Method, Der Chem. Sinica, 4, 79 (2013).
V.G. Kadajji and G.V. Betageri, Water Soluble Polymers for Pharmaceu-tical Applications, Polymers, 3, 1972 (2011); https://doi.org/10.3390/polym3041972.
D.S. Wagare, D. Lingampalle, M. Farooqui and A. Durrani, An Enviorn-mentally Benign One-Pot Synthesis of 3-Arylfuro[3,2-c]coumarins in PEG-400 and Water, Der Pharm. Chem., 8, 408 (2016).
D.S. Wagare, M. Farooqui, T.D. Keche and A. Durrani, Efficient and Green Microwave-Assisted One-Pot Synthesis of Azaindolizines in PEG-400 and Water, Synth. Commun., 46, 1741 (2016); https://doi.org/10.1080/00397911.2016.1223314.
M.A. Brook and T.H. Chan, A Simple Procedure for the Esterification of Carboxylic Acids, Synthesis, 201 (1983); https://doi.org/10.1055/s-1983-30279.
T.H. Chan, M.A. Brook and T. Chaly, A Simple Procedure for the Acetalization of Carbonyl Compounds, Synthesis, 203 (1983); https://doi.org/10.1055/s-1983-30280.

References

G. Beck and H. Heitzer, Preparation of 2-Chloro-5-Chloromethylthiazole, US Patent 4,7482,43A (1988).

F.W. Bell, A.S. Cantrell, M. Hoegberg, S.R. Jaskunas, N.G. Johansson, C.L. Jordan, M.D. Kinnick, P. Lind and J.M. Morin, Phenethylthiazole-thiourea (PETT) Compounds, A New Class of HIV-1 Reverse Transcrip-tase Inhibitors. 1. Synthesis and Basic Structure-Activity Relationship Studies of PETT Analogs, J. Med. Chem., 38, 4929 (1995); https://doi.org/10.1021/jm00025a010.

W.C. Patt, H.W. Hamilton, M.D. Taylor, M.J. Ryan, D.G. Taylor, C.J.C. Connolly, A.M. Doherty, S.R. Klutchko and I. Sircar, Structure-Activity Relationships of a Series of 2-Amino-4-thiazole containing Renin Inhibitors, J. Med. Chem., 35, 2562 (1992); https://doi.org/10.1021/jm00092a006.

T.K. Venkatachalam, E.A. Sudbeck, C. Mao and F.M. Uckun, Anti-HIV Activity of Aromatic and Heterocyclic Thiazolyl Thiourea compounds, Bioorg. Med. Chem. Lett., 11, 523 (2001); https://doi.org/10.1016/S0960-894X(01)00011-7.

F. Clemence, O. Le Martret, F. Delevallee, J. Benzoni, A. Jouanen, S. Jouquey, M. Mouren and R. Deraedt, 4-Hydroxy-3-quinolinecarboxamides with Antiarthritic and Analgesic Activities, J. Med. Chem., 31, 1453 (1988); https://doi.org/10.1021/jm00402a034.

K. Tsuji and H. Ishikawa, Synthesis and Anti-Pseudomonal Activity of New 2-Isocephems with a Dihydroxypyridone Moiety at C-7, Bioorg. Med. Chem. Lett., 4, 1601 (1994); https://doi.org/10.1016/S0960-894X(01)80574-6.

M.C. Wilkes, P.B. Lavrik and J. Greenplate, Synthesis of N-Benzoyl-N-alkyl-2-aminothiazoles: Heliothis virescens Proinsecticides, J. Agric. Food Chem., 39, 1652 (1991); https://doi.org/10.1021/jf00009a023.

N. Vukovic, S. Sukdolak, S. Solujic and T. Milosevic, Synthesis and Antimicrobial Evaluation of Some Novel 2-Aminothiazole Derivatives of 4-Hydroxychromene-2-one, Arch. Pharm., 341, 491 (2008); https://doi.org/10.1002/ardp.200700215.

H.L. Chang, H.L. Lin, Y.C. Wang, S.A. Dai, W.C. Su and R.J. Jeng, Thermally Stable NLO Poly(amide-imide)s via Sequential Self-Repetitive Reaction, Polymer, 48, 2046 (2007); https://doi.org/10.1016/j.polymer.2007.02.010.

T. Baehr-Jones, M. Hochberg, G. Wang, R. Lawson, Y. Liao, P.A. Sullivan, L. Dalton, A.K.-Y. Jen and A. Scherer, Optical Modulation and Detection in Slotted Silicon Waveguides, Opt. Express, 13, 5216 (2005); https://doi.org/10.1364/OPEX.13.005216.

Y. Cui, H. Ren, J. Yu, Z. Wang and G. Qian, An Indanone-Based Alkoxy-silane Dye with Second Order Nonlinear Optical Properties, Dyes Pigments, 81, 53 (2009); https://doi.org/10.1016/j.dyepig.2008.09.002.

F. Qiu, Y. Zhou, J. Liu and X. Zhang, Preparation, Morphological and Thermal Stability of Polyimide/Silica Hybrid Material Containing Dye NBDPA, Dyes Pigments, 71, 37 (2006); https://doi.org/10.1016/j.dyepig.2005.05.009.

P.L. Lobo, B. Poojary, M. Kumsi, V. Chandra, N.S. Kumari and K.R. Chandrashekar, Synthesis, Antimicrobial and Antioxidant Activities of 2-[1-{3,5-Diaryl-4,5-dihydro-1H-pyrazolenyl}]-4-(4-nitrophenyl)-[1,3]thiazoles, Med. Chem. Res., 22, 1689 (2013); https://doi.org/10.1007/s00044-012-0154-3.

K. Hazra, L.V.G. Nargund, P. Rashmi, J.N.N. Sharath Chandra and B. Nandha, Synthesis and Antioxidant Activity of Some Novel Fluorobenzo-thiazolopyrazoline, Der Chem. Sinica, 2, 149 (2011).

B.P. Bandgar, S.S. Gawande, R.G. Bodade, N.M. Gawande and C.N. Khobragade, Synthesis and Biological Evaluation of a Novel Series of Pyrazole Chalcones as Anti-Inflammatory, Antioxidant and Antimicro-bial Agents, Bioorg. Med. Chem., 17, 8168 (2009); https://doi.org/10.1016/j.bmc.2009.10.035.

A.M. Youssef, M.S. White, E.B. Villanueva, I.M. El-Ashmawy and A. Klegeris, Synthesis and Biological Evaluation of Novel Pyrazolyl-2,4-thiazolidinediones as Anti-Inflammatory and Neuroprotective Agents, Bioorg. Med. Chem., 18, 2019 (2010); https://doi.org/10.1016/j.bmc.2010.01.021.

R.Verma, P. Chawla and S.K. Saraf, Syntheses, Characterization and Evaluation of Some 1,3,4-Trisubstituted-5-pyrazolone Derivatives as Dual Anti-Inflammatory and Antimicrobial Agents, Der Pharm. Sinica, 3, 546 (2012).

P.N. Balaji, L.K. Lakshmi, K. Mohan, K. Revathi, A. Chamundeswari and P.M. Indrani, In-vitro Anti-Inflammatory and Antimicrobial Activity of Synthesized Some Novel Pyrazole Derivatives from Coumarin Chalcones, Der Pharm. Sinica, 3, 685 (2012).

A. Özdemir, G. Turan-Zitouni, Z. Asim Kaplancikli, G. Revial and K. Güven, Synthesis and Antimicrobial Activity of 1-(4-Aryl-2-thiazolyl)-3-(2-thienyl)-5-aryl-2-pyrazoline Derivatives, Eur. J. Med. Chem., 42, 403 (2007); https://doi.org/10.1016/j.ejmech.2006.10.001.

Ch.S. Reddy, M.V. Devi, G.R. Kumar, L.S. Rao and A. Nagaraj, Synthesis and Antimicrobial Activity of Linked Heterocyclics Containing Pyrazole-Pyrimidine Rings, Indian J. Chem., 50B, 1181 (2011).

P. Patel, D. Gor and P.S. Patel, Synthesis, Characterization and Anti-microbial Activities of N-[{4-[2-{3,5-bis(4-Methoxyphenyl)-4,5-dihydro-pyrazol-yl}-2-oxoethoxy]phenyl}methylene] Substituted Aniline, Der Chem. Sinica, 3, 896 (2012).

S. Kumar, G. Kumar, M. Kapoor, A. Surolia and N. Surolia, Synthesis and Evaluation of Substituted Pyrazoles: Potential Antimalarials Targeting the Enoyl-ACP Reductase of Plasmodium Falciparum, Synth. Commun., 36, 215 (2006); https://doi.org/10.1080/00397910500334561.

S. Chandrasekhar, C. Narsihmulu, G. Chandrashekar and T. Shyamsunder, Pd/CaCO3 in Liquid Poly(ethylene glycol) (PEG): An Easy and Efficient Recycle System for Partial Reduction of Alkynes to cis-Olefins under a Hydrogen Atmosphere, Tetrahedron Lett., 45, 2421 (2004); https://doi.org/10.1016/j.tetlet.2004.01.097.

M.H. Shaikh, D.S. Wagare, M. Farooqui and A. Durrani, Facile and Green One-Pot Synthesis of 2-aminothiazoles in Glycerol-Water, Heterocycl. Lett., 7, 1061 (2017).

D.S. Wagare, P.D. Netankar, M. Shaikh, M. Farooqui and A. Durrani, Highly Efficient Microwave-Assisted One-Pot Synthesis of 4-Aryl-2-amino-thiazoles in Aqueous Medium, Environ. Chem. Lett., 15, 475 (2016); https://doi.org/10.1007/s10311-017-0619-1.

V. Ravibabu, B. Janardhan, G. Rajitha and B. Rajitha, Efficient One-Pot Three-component Synthesis of Thiazolyl Pyrazole Derivatives under Conventional Method, Der Chem. Sinica, 4, 79 (2013).

V.G. Kadajji and G.V. Betageri, Water Soluble Polymers for Pharmaceu-tical Applications, Polymers, 3, 1972 (2011); https://doi.org/10.3390/polym3041972.

D.S. Wagare, D. Lingampalle, M. Farooqui and A. Durrani, An Enviorn-mentally Benign One-Pot Synthesis of 3-Arylfuro[3,2-c]coumarins in PEG-400 and Water, Der Pharm. Chem., 8, 408 (2016).

D.S. Wagare, M. Farooqui, T.D. Keche and A. Durrani, Efficient and Green Microwave-Assisted One-Pot Synthesis of Azaindolizines in PEG-400 and Water, Synth. Commun., 46, 1741 (2016); https://doi.org/10.1080/00397911.2016.1223314.

M.A. Brook and T.H. Chan, A Simple Procedure for the Esterification of Carboxylic Acids, Synthesis, 201 (1983); https://doi.org/10.1055/s-1983-30279.

T.H. Chan, M.A. Brook and T. Chaly, A Simple Procedure for the Acetalization of Carbonyl Compounds, Synthesis, 203 (1983); https://doi.org/10.1055/s-1983-30280.

Trimethylsilyl Chloride Catalyzed Highly Efficient Synthesis of Schiff Bases of Thiazole in Glycerol under Microwave Irradiation

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