IJOC  Vol.2 No.1 , March 2012
A New and Efficient Method for the Synthesis of Pyrimido[2,1-b]Benzothiazole Derivatives
ABSTRACT
The one-pot three-component reaction of 2-aminobenzothiazole, benzaldehyde derivatives and β-ketoester, β-diketone or malonate derivatives in solvent-free conditions provides the corresponding pyrimido [2,1-b] benzothiazole derivatives at 60?C in 60% - 72% yields without using any catalyst in an optimistic time.

Cite this paper
F. Chadegani, F. Darviche and S. Balalaie, "A New and Efficient Method for the Synthesis of Pyrimido[2,1-b]Benzothiazole Derivatives," International Journal of Organic Chemistry, Vol. 2 No. 1, 2012, pp. 31-37. doi: 10.4236/ijoc.2012.21006.
References
[1]   G. P. Ellis, “Chemistry of Heterocyclic Compounds: Synthesis of Fused Heterocycles,” John Wiley & Sons, Ltd., New York, Vol. 47, 2008.

[2]   A. Burger, “Medicinal Chemistry,” 7th Edition, Wiley-Interscience, New York, 2010, p. 72.

[3]   G. Trapani, A. Franco, G. Latrofa, A. Carotti, G. Genchi, M. Serra, G. Biggioand and G. Liso, “Synthesis and Benzodiazepine Receptor Binding of Some Imidazo- and Pyrimi-do[2,1-b]benzothiazoles,” European Journal of Medicinal Chemistry, Vol. 31, No. 7-8, 1996, pp. 575- 587. doi:10.1016/0223-5234(96)89553-5

[4]   G. Trapani, A. Carotti, A. Franco, G. Latrofa, G. Gench and G. Liso, “Structure-Affinity Relationships of Some Alkoxycarbonyl-2H- or -4H-Pyrimido [2,1-b]benzothia- zol-2- or 4-one Benzodiazepine Receptor Ligands,” European Journal of Medicinal Chemistry, Vol. 28, No. 1, 1993, pp. 13-21. doi:10.1016/0223-5234(93)90074-O

[5]   M. M. M. Gineinah, “6-, 7- and 8-(5-Aryl-1-phenyl- 2-pyrazolin-3-yl) Imidazo- and Pyrimido[2,1-b] Ben-zothiazoles as Novel Anticonvulsant Agents,” Scientia Pharmaceutica, Vol. 69, No. 1, 2001, pp. 53-61.

[6]   I. M. Batulin, “On the Mechanism of the Anti-convulsant Action of Some Derivatives of Pyrazole,” Farma-kologiya Toksikologiya, Vol. 31, No. 5, 1968, pp. 533-536.

[7]   S. S. Parmar, B. R. Pandey, C. Dwivediand and R. D. Harbison, “Anticonvulsant Activity and Monoamine Oxidase Inhibitory Properties of 1,3,5 Trisubstitute dpyrazo-lines,” Journal of Pharmaceutical Sciences, Vol. 63, No. 7, 1974, pp. 1152-1155. doi:10.1002/jps.2600630730

[8]   J. J. Wade, C. B. Tose, C. J. Matson and V. L. Stelzer, “Synthesis and Antiallergic Activity of Some Acidic Derivatives of 4H-Pyrimido[2,1-b]benzazol-4-ones,” Journal of Medicinal Chemistry, Vol. 26, No. 4, 1983, pp. 608-611. doi:10.1021/jm00358a031

[9]   R. J. Alaimo, “The Synthesis of Some 4H Pyrimido[2,1 b]benzothiazol 4 Ones,” Journal of Heterocyclic Chemistry, Vol. 10, No. 5, 1973, pp. 769-772. doi:10.1002/jhet.5570100515

[10]   A. Gupta and S. Rawat, “Synthesis and Cyclization of Benzothiazole: Review,” Journal of Current Pharmaceutical Research, Vol. 3, No. 1, 2010, pp. 13-23.

[11]   A. Bartovic, D. Ilavski, O. Simo, L. Zalibera, A. Belicová and M. Seman, “Synthesis of Nitro-Substituted 4-Oxo- 4H-pyrimido[2,1-b]benzothiazole-3-carboxylic Acids and Their Spectral Characteristics,” Collection of Czechoslo- vak Chemical Communications, Vol. 60, No. 4, 1995, pp. 583-593. doi:10.1135/cccc19950583

[12]   M. A. El-Sherbeny, “Synthesis of Certain Pyrimido[2,1- b]benzothiazole and Ben-zothiazolo[2,3-b]quinazoline Derivatives for in vitro Antitumor and Antiviral Activities,” Arzneimittel-Forschung/Drug Re-search, Vol. 50, No. 9, 2000, pp. 848-853.

[13]   J. P. Yevich, D. L. Temple, R. R. Covington, D. A. Owens, R. J. Seidehameland and K. W. Dungan, “Antial- lergics: 3-(1H-tetrazol-5-yl)-4H-pyrimido[2,1- b]ben-zothi- azol-4-ones,” Journal of Medicinal Chemistry, Vol. 25, No. 7, 1982, pp. 864-868. doi:10.1021/jm00349a020

[14]   A. Kutyrev and T. Kappe, “Methanetricarboxylates as Key Reagents for the Simple Preparation of Heteroary- lcarboxamides with Potential Biological Activity. Part 2[1]. Reaction of Methanetricarbox-ylates with 2-Amino- pyridine, 2-Aminopyrimidine, 2-Aminothiazole and 2- Aminobenzothiazole,” Journal of Hete-rocyclic Chemistry, Vol. 36, No. 1, 1999, pp. 237-240. doi:10.1002/jhet.5570360136

[15]   C. Landreau, D. Deniaud, M. Evain and A. Reliquet, “Ef- ficient Regioselective Synthesis of Triheterocyclic Com- pounds: Imidazo[2,1-b]benzothiazoles, Pyrimido[2,1-b]- benzothiazolones and Pyrimi-do[2,1-b]benzothiazoles,” Journal of the Chemical Society, Perkin Transactions 1, No. 6, 2002, pp. 741-745.

[16]   P. J. Roy, K. Landry and Y. Leblanc, “Condensation of 2-Amino-5-chlorobenzoxazole with α-Bromoketones: A Mechanistic Study,” Heterocycles, Vol. 45, No. 11, 1997, pp. 2239-2246.

[17]   Y. Tanabe, A. Kawai, Y. Yoshida, M. Ogure and H. Okumura, “Preparation of Fused Thiadiazolo- and Im-idazobenzothiazoles from 2-Aminobenzothiazoles. Their Fungicidal Activity,” Heterocycles, Vol. 45, No. 8, 1997, pp. 1579-1588. doi:10.3987/COM-97-7839

[18]   G. Trapani, A. Frang, G. Latrofa and G. Genchi, “Synthesis and Benzodiaze-pine Receptor Binding of Some 4H- Pyrimi-do[2,1-b]benzothiazol-4-ones,” European Journal of Medicinal Chemistry, Vol. 27, No. 1, 1992, pp. 39-44. doi:10.1016/0223-5234(92)90058-9

[19]   H. Ogura, M. Kawa-no and T. Itoh, “Studies on Hetero-cyclic Compounds. XIII. Reaction of 2 Aminobenzazoles with Acetylenic Compounds,” Chemical Pharmaceutical Bulletin, Vol. 21, No. 9, 1973, pp. 2019-2025. doi:10.1248/cpb.21.2019

[20]   H. N. Al-Jallo and M. A. Mu-niem, “Synthesis and Nu- clear Magnetic Resonance Spectra of Fused Pyrimidines,” Journal of Heterocyclic Chemistry, Vol. 15, No. 8, 1978, pp. 849-853. doi:10.1002/jhet.5570150525

[21]   C. K. Chan, J. C. N. Ma and T. C. W. Mak, “Synthesis and X-ray structure of methyl 2-oxopyrimido[2,1-b]ben- zothiazole-4-carboxylate from condensation of 2-aminobenzothiazole and dimethyl but-2-ynedioate,” Journal of the Chemical Society, Perkin Transactions 2, No. 8, 1977, pp. 1070-1074.

[22]   J. J. Wade, R. F. Hegel and C. B. Toso, “Reaction of 2-Aminobenzazoles with Dimethyl 2-Aminofumarate. Synthesis and Nuclear Magnetic Resonance Spectroscopy of 4-Oxopyrimido[2,1-b]benzazoles,” The Journal of Organic Chemistry, Vol. 44, No. 11, 1979, pp. 1811- 1816. doi:10.1021/jo01325a013

[23]   H. Wahe, J. T. Mbafor, A. E. Nkengfack, Z. T. Fomum, R. A. Cherkasov, O. Sterner and D. Doepp, “Heterocycles of Biological Importance: Part 7. Syn-thesis of Biologicallyactivepyrimido[2,1-b]benzothiazoles from Acetylenic Acids and2-Aminobenzothiazoles,” Arkivoc, Vol. 2003, No. 15, 2003, pp. 107-114.

[24]   A. Santagati, M. San-tagati, F. Russo and G. Ronsisvalle, “Condensed Heterocycles Containing the Pyrimidine Nucleus,” Journal of Heterocyclic Chemistry, Vol. 25, No. 3, 1988, pp. 949-953. doi:10.1002/jhet.5570250347

[25]   D. W. Dunwell and D. Evans “The Reactions of 2-Aminothiazoles and 2-Aminobenzothiazoles with Propiolic Acid and Its Esters,” Journal of the Chemical Society C: Organic Chemistry, 1971, pp. 2094-2097.

[26]   A. A. Pavlenko, Kh. S. Shikhaliev, Yu. A. Potapov and D. V. Krylsky, “Three-Component Reaction of 2-Amino- benzothiazole with Methylene-Active Carbonyl Compounds and Aldehydes,” Chemistry of Heterocyclic Compound, Vol. 41, No. 5, 2005, pp. 689-690. doi:10.1007/s10593-005-0206-4

[27]   A. Shaabani, A. Rahmati and S. Naderi, “A Novel One-Pot Three-Component Reaction: Synthesis of Tri- heterocyclic 4H-Pyrimido[2,1-b]benzazoles Ring Sys- tems,” Bioorganic and Medicinal Chemistry Letters, Vol. 15, No. 24, 2005, pp. 5553-5557. doi:10.1016/j.bmcl.2005.08.101

[28]   H. Ogura and T. ITOH, “Derivatives of Imidazo [2, 1-b] benzothiazole (Studies on Heterocyclic Compounds. VII),” Chemical & Pharmaceutical Bulletin, Vol. 18, No. 10, 1970, pp. 1981-1986. doi:10.1248/cpb.18.1981

[29]   A. Kreutzberger and M. Leger, “Centrally Dampening Drugs. 3rd Communication: 3-Aromatic-Aliphatically Substituted 4-Hydrox-ypyrimido[1,2-α]benzimidazole-2- ones,” Arzneimit-tel-Forschung/Drug Research, Vol. 33, No. 11, 1983. pp. 1517-1518.

[30]   M. Bararjanian, S. Balalaie, F, Rominger, B. Movassagh and H. R. Bijanzadeh, “Six-Component Reactions for the Stereoselective Synthesis of 3-Arylidene-2-oxindoles via Sequential One-Pot Ugi/Heck Carbocyclization/ Sonoga- shi-ra/Nucleophilic Addition,” The Journal of Organic Chemistry, Vol. 75, No. 9, 2010, pp. 2806-2812. doi:10.1021/jo902713x

[31]   M. Bararjanian, S. Balalaie, B. Movassagh, H. R. Bi- janzadeh, “Efficient Synthesis of 1,4-Disubstituted Polyfunctionalpiperazines via a Sequential One-Pot Ugi/Nu- cleophilic Addition Five-Component Reaction,” Tetrahedron Letter, Vol. 51, No. 25, 2010, pp. 3277-3279. doi:10.1016/j.tetlet.2010.04.054

[32]   M. J. Khoshkholgh, M. Lotfi, S. Balalaie and F. Rom- inger, “Efficient Synthesis Of Pyrano[2,3-c]coumarins via Intramolecular Domino Knoeve-nagel Hetero-Diels-Alder Reactions,” Tetrahedron, Vol. 65, No. 21, 2009, pp. 4228-4234. doi:10.1016/j.tet.2009.03.032

[33]   M. Bararjanian, S. Hosseinzadeh, S. Balalaie, H. R. Bi- janzadeh, “Palladium Catalyzed Stereoselective Synthesis of 3-(Anilinoarylmethylene)-2-oxindoles as Hesperadin Analo-gues,” Tetrahedron, Vol. 67, No. 14, 2011, pp. 2644-2650. doi:10.1016/j.tet.2011.02.005

[34]   M. Bararjanian, S. Balalaie, B. Movassagh, F. Rominger and H. R. Bijanzadeh, “Novel and Efficient One-Pot Five- and Six-Component Reactions for the Stereoselective Synthesis of Highly Functionalized Enaminones and Dithiocarbamates,” Molecular Diversity, Vol. 15, No. 2, 2011, pp. 583-594. doi:10.1007/s11030-010-9286-x

[35]   M. Hadjebi, M. S. Hash-troudi, H R. Bijanzadeh and S. Balalaie, “Novel Four-Component Approach for the Synthesis of Polyfunctiona-lized 1,4-Dihydropyridines in Aqueous Media,” Helvetica Chimica Acta, Vol. 94, No. 3, 2011, pp. 382-388. doi:10.1002/hlca.201000228

 
 
Top