A series of spiro, β -Lactams, and thiazolidinones incorporating compounds 4 have been synthesized by cycloaddition reaction of, chloroacetyl chloride and mercaptoacetic acid with the synthesized Shiff,s bases 5a-c to give new spiro β - Lactam 6a-c and spiro thiazolidinone 7a-c the cycloaddition were characterized by spectral data including HNMR, 13 C-NMR, IR and elemental analysis.
R. Southgate, “The Synthesis of Natural β-Lactam Antibiotics,” Contemporary Organic Synthesis, Vol. 1, No. 6, 1994, pp. 417-431. doi:10.1039/co9940100417
F. Broccolo, G. Carnally, G. Caltabiano, C. E. A. Cocuzza, C. Fortuna, G. Galletti, P. D. Giacomini, G. Musumarra, R. Musumeci and A. Quitavalla, “Design, Synthesis, and Biological Evaluation of 4-Alkyliden-Beta Lactams: New Products with Promising Antibiotic Activity against resIstant Bacteria,” Journal of Medicinal Chemistry, Vol. 49, No. 9, 2006, pp. 2804-2811. doi:10.1021/jm0580510
B. Alcaide, P. Almendros and C. Aragoncillo, “β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products,” Chemical Reviews, Vol. 107, 2007, pp. 4437-4492.
B. Alcaide and P. Almendros, “β-Lactams as Versatile Intermediates for the Preparation of Heterocycles of Biological Interest,” Current Medicinal Chemistry, Vol. 11, No. 14, 2004, pp. 1921-1949. doi:10.2174/0929867043364856
A. R. A. S. Deshmukh, B. M. Bhawal, D. Krishnaswamy, V. V. Govande, B. A. Shinkre and A. Jayanthi, “Azetidin-2-Ones, Synthon for Biologically Important Compounds,” Current Medicinal Chemistry, Vol. 11, No. 14. 2004, pp. 1889-1920. doi:10.2174/0929867043364874
B. Alcaide and P. Almendros, “Selective Bond Cleavage of the β-Lactam Nucleus: Application in Stereocontrolled Synthesis,” Synlett, Vol. 3, 2002, pp. 381-393. doi:10.1055/s-2002-20448
C. Palomo, J. M. Aizpurua, I. Ganboa and M. Oiarbide, “β-lactams as Versatile Intermediates in α- and β-Amino Acid Synthesis,” Synlett, Vol. 12, 2001, pp. 1813-1826. doi:10.1055/s-2001-18733
I. Ojima, “The Organic Chemistry of β-Lactams,” G. I. Georg, Ed., VCH, New York, 1993, pp. 197-255.
I. Ojima, “Recent Advances in the β-Lactam Synthon Method,” Accounts of Chemical Research, Vol. 28, No. 9, 1995, pp. 383-389. doi:10.1021/ar00057a004
M. O’Driscoll, K. Greenhalgh, A. Young, E. Turos, S. Dickey and D. V. Lim, “Studies on the Antifungal Properties of N-Thiolated β-Lactams,” Bioorganic & Medicinal Chemistry, Vol. 16, No. 16, 2008, pp. 7832-7837. doi:10.1016/j.bmc.2008.06.035
E. Turos, G. S. K. Reddy, K. Greenhalgh, P. Ramaraju, S. C. Abeylath, S. Jang, S. Dickey and D. V. Lim, “Penicillin-Bound Polyacrylate Nanoparticles: Restoring the Activity of β-Lactam Antibiotics against MRSA,” Bioorganic & Medicinal Chemistry Letters, Vol. 17, No. 12, 2007, pp. 3468-3472. doi:10.1016/j.bmcl.2007.03.077
S. Dugar, N. Yumibe, J. W. Clader, M. Vizziano, K. Huie, M. van Heek, D. S. Compton and H. R. Davis Jr., “Metabolism and Structure Activity Data Based Drug Design: Discovery of (?) SCH53079 an Analog of the Potent Cholesterol Absorption Inhibitor (?) SCH 48461,” Bioorganic & Medicinal Chemistry Letters, Vol. 6, No. 11, 1996, pp. 1271-1274. doi:10.1016/0960-894X(96)00214-4
W. T. Han, A. K. Trehan, J. J. K. Wright, M. E. Federici, S. M. Seiler and N. A. Meanwell, “Azetidin-2-One Derivatives as Inhibitors of Thrombin,” Bioorganic & Medicinal Chemistry, Vol. 3, No. 8, 1995, pp. 1123-1143. doi:10.1016/0968-0896(95)00101-L
A. D. Borthwick, G. Weingarte, T. M. Haley, M. Tomaszewski, W. Wang, Z. Hu, J. Bedard, H. Jin, L. Yuen and T. S. Mansour, “Design and Synthesis of Monocyclic β-Lactams as Mechanismbased Inhibitors of Human Cytomegalovirus Protease,” Bioorganic & Medicinal Chemistry Letters, Vol. 8, No. 4, 1998, pp. 365-370. doi:10.1016/S0960-894X(98)00032-8
G. Cainelli, P. Galletti, S. Garbisa, D. Giacomini and L.Sartor, “Quintavalla, A. 4-Alkylideneazetidin-2-Ones: Novel Inhibitors of Leukocyte Elastase and Gelatinase,” Bioorganic & Medicinal Chemistry, Vol. 11, No. 24, 2003, pp. 5391-5399. doi:10.1016/j.bmc.2003.09.035
N. E. Zhou, D. Guo, G.Thomas, A. V. N. Reddy, J. Kaleta, E. Purisima, R. Menard, R. G. Micetich and R. Singh, “3-Acylamino-Azetidin-2-One as a Novel Class of Cysteine Proteases Inhibitors,” Bioorganic & Medicinal Chemistry Letters, Vol. 13, No. 1, 2003, pp. 139-141. doi:10.1016/S0960-894X(02)00831-4
A. Kazi, R. Hill, T. E. Long, D. J. Kuhn, E. Turos and Q. P. Dou, “Novel N-Thiolated β-Lactam Antibiotics Selectively Induce Apoptosis in Human Tumor and Transformed, but Not Normal or Nontransformed, Cells,” Biochemical Pharmacology, Vol. 67, No. 2, 2004, pp. 365-374. doi:10.1016/j.bcp.2003.09.017
E. Alonso, F. Lopez-Ortiz, C. Del Pozo, E. Peratta, A. Macias and J. Gonzalaz, “Spiro β-Lactams as β-Turn Mimetics. Design, Synthesis, and NMR Conformational Analysis,” The Journal of Organic Chemistry, Vol. 66, No. 19, 2001, pp. 6333-6338. doi:10.1021/jo015714m
H. Bittermann and P. Gmeiner, “Chirospecific Synthesis of Spirocyclic β-Lactams and Their Characterization as Potent Type ii β-Turn Inducing Peptide Mimetics,” The Journal of Organic Chemistry, Vol. 71, No. 1, 2006, pp. 97-102. doi:10.1021/jo0517287
E. Alonso, C. Del Pozo and J. Gonzalez, “Synthesis of α,α-Disubstituted β-Amino Esters and Peptide Derivatives,” Synlett, Vol. 1, 2002, pp. 69-72. doi:10.1055/s-2002-19326
J. L. Pinder and S. M. Weinreb, “Preliminary Feasibility Studies on Total Synthesis of the Unusual Marine Bryozoan Alkaloids Chartellamide A and B,” Tetrahedron Letters, Vol. 44, No. 21, 2003, pp. 4141-4143. doi:10.1016/S0040-4039(03)00876-1
J. W. Skiles and D. McNeil, “Spiro Indolinone Beta-Lactams, Inhibitors of Poliovirus and Rhinovirus 3c-Proteinases,” Tetrahedron Letters, Vol. 31, No. 50, 1990, pp. 7277-7280. doi:10.1016/S0040-4039(00)88543-3
A. Jarrahpour and D. Khalili, “Synthesis of Some Mono- and Bis-Spiro-β-Lactams of Benzylisatin,” Tetrahedron Letters, Vol. 48, No. 40, 2007, pp. 7140-7143. doi:10.1016/j.tetlet.2007.07.199
X. Lin and S. M. Weinreb, “Model Studies on Total Synthesis of the Chartellines, Spirocyclic β-Lactam Alkaloids from a Marine Bryozoan,” Tetrahedron Letters, Vol. 42, No. 14, 2001, pp. 2631-2633. doi:10.1016/S0040-4039(01)00270-2
S. Anklam and J. Liebscher, “Synthesis of Optically Active Spiro-β-Lactams by Cycloadditions to α-Alkylidene- β-Lactams,” Tetrahedron, Vol. 54, No. 23, 1998, pp. 6369-6384. doi:10.1016/S0040-4020(98)00296-8
B. Alcaide, P. Almendros, T. M. Del Campo, R. Rodríguez-Acebes, “Diversity-Oriented Preparation of Enantiopure Spirocyclic 2-Azetidinones from α-Oxo-β-Lactams through Barbier-Type Reactions Followed by Metal-Catalyzed Cyclizations,” Advanced Synthesis & Catalysis, Vol. 349, No. 4-5, 2007, pp. 749-758. doi:10.1002/adsc.200600502
A. Gareth, C. Jonathan and D. H. Stuart, “Azabicyclic Amino Acids by Stereoselective Dearomatizing Cyclization of the Enolates of N-Nicotinoyl Glycine Derivatives,” Organic Letters, Vol. 8, No. 23, 2006, pp. 5325- 5328. doi:10.1021/ol062126s
A. Bhalla, P. Venugopalan and S. S. Bari, “A New Synthetic Approach to Novel Spiro-β-Lactams,” European Journal of Organic Chemistry, Vol. 2006, No. 21, 2006, pp. 4943-4950. doi:10.1002/ejoc.200600458
A. Zanobini, A. Brandi and A. De Meijere, “A New Three-Component Cascade Reaction to Yield 3-Spirocyclopropanated β-Lactams,” European Journal of Organic Chemistry, Vol. 2006, No. 5, 2006, pp. 1251-1255. doi:10.1002/ejoc.200500838
A. Zanobini, M. Gensini, J. Magull, D. Vidovic, S. I. Kozhushkov, A. Brandi and A. De Meijere, “A Convenient New Synthesis of 3-Substituted β-Lactams Formally Derived from 1-(Aminomethyl)cyclopropanecarboxylic acids,” European Journal of Organic Chemistry, Vol. 2004, No. 20, 2004, pp. 4158-4166. doi:10.1002/ejoc.200400392
B. Alcaide, P. Almendros and R. Rodríguez-Acebes, “Pd-Cu Bimetallic Catalyzed Domino Cyclization of α-Allenols Followed by a Coupling Reaction: New Sequence Leading to Functionalized Spirolactams,” Chemistry of the European Journal, Vol. 11, No. 19, 2005, pp. 5708-5712. doi:10.1002/chem.200500228
A. Bhalla, P. Venugopalan, K. K. Bhasin and S. S. Bari, “Seleno-β-Lactams: Synthesis of Monocyclic and Spirocyclic Selenoazetidin-2-Ones,” Tetrahedron, Vol. 63, No. 15, 2007, pp. 3195-3204. doi:10.1016/j.tet.2007.02.001
C. V. Galliford, J. S. Martenson, C. Stern and K. A. Scheidt, “A Highly Diastereoselective, Catalytic three- Component Assemblyreaction for the Synthesis of Spiropyrrolidinyloxindoles,” Chemical Communications, Vol. 2007, No. 6, 2007, pp. 631-633. doi:10.1039/b609155e
C. Sun, X. Lin and M. Weinreb, “Explorations on the Total Synthesis of the Unusual Marine Alkaloid Chartelline A,” The Journal of Organic Chemistry, Vol. 71, No. 8, 2006, pp. 3159-3166. doi:10.1021/jo060084f
B. Alcaide, P. Almendros and R. Rodr?′guez-Acebes, “Efficient Entry to Diversely Functionalized Spirocyclic Oxindoles from Isatins through Carbonyl-Addition/Cyclization Reaction Sequences,” The Journal of Organic Chemistry, Vol. 71, No. 6, 2006, pp. 2346-2351. doi:10.1021/jo0525027
G. Cremonesi, P. Dalla Croce and C. La Rosa, “Synthesis of Imidazo[5,1-b]thiazoles or Spiro-β-Lactams by Reaction of Imines with Mesoionic Compounds or Ketenes Generated from N-Acylthiazolidine-2-Carboxylic Acids,” Tetrahedron, Vol. 60, No. 1, 2004, pp. 93-97. doi:10.1016/j.tet.2003.10.093
B. Alcaide, P. Almendros, T. M. Del Campo and R. Rodr?′guez-Acebes, “Metal-Assisted Synthesis of Enantiopure Spirocyclic β-Lactams from Azetidine-2,3- Diones,” Tetrahedron Letters, Vol. 45, No. 34, 2004, pp. 6429-6431. doi:10.1016/j.tetlet.2004.06.130
N. Toshio, K. Shigeo and I. Minoru, “Novel Synthesis of Bromoindolenine with Spiro-Blactam in Chartelline,” Synlett, Vol. 2004, 2004, pp. 2025-2027.
O. Arjona, A. G. Csa`ky, M. C. Murcia and J. Plumet, “The Staudinger Reaction of Imines derived from 7-Oxanorbornenone: Formation of Spiranic Oxazinone versus β-Lactam Rings,” Tetrahedron Letters, Vol. 43, No. 36, 2002, pp. 6405-6408. doi:10.1016/S0040-4039(02)01375-8
E. Alonso, C. Del Pozo and J. Gonzalez, “Staudinger Reactions of Unsymmetrical Cyclic Ketenes: A Synthetically Useful Approach to Spiro β-Lactams and Derivatives. Reaction Mechanism and Theoretical Studies,” Journal of the Chemical Society, Perkin Transactions, Vol. 1, No. 4, 2002, pp. 571-576. doi:10.1039/b103279h
I. R. Cooper, R. Grigg, W. S. MacLachlan and M. Thornton-Pett, V. Sridharane, “3-Component Palladium-Indium Mediated Diastereoselective Cascade Allylation of Imines with Allenes and Aryl Iodides,” Chemical Communications, Vol. 13, 2002, pp. 1372-1373. doi:10.1039/b202940e
C. Palomo, J. M. Aizpurua, I. Ganboa and M. Oiarbide, “Asymmetric Synthesis of β-Lactams through the Staudinger Reaction and Their Use as Building Blocks of Natural and Nonnatural Products,” Current Medicinal Chemistry, Vol. 11, No. 14, 2004, pp. 1837-1872. doi:10.2174/0929867043364900
I. Banik, F. F. Becker and B. K. Banik, “Stereoselective Synthesis of β-Lactams with Polyaromatic Imines: Entry to New and Novel Anticancer Agents,” Journal of Medicinal Chemistry, Vol. 46, No. 1, 2003, pp. 12-15. doi:10.1021/jm0255825
B. K. Banik, F. F. Becker and I. Banik, “Synthesis of Anticancer β-Lactams: Mechanism of Action,” Bioorganic & Medicinal Chemistry, Vol. 12, No. 10, 2004, pp. 2523-2528. doi:10.1016/j.bmc.2004.03.033
F. F. Becker and B. K. Banik, “Polycyclic Aromatic Compounds as Anticancer Agents: Synthesis and Biological Evaluation of Some Chrysene Derivatives,” Bioorganic & Medicinal Chemistry Letters, Vol. 8, No. 20, 1998, pp. 2877-2880. doi:10.1016/S0960-894X(98)00520-4
A. K. Khalafallah, R. M. Abdel Aal and N. A. A. Elkanzi “Synthesis of Some New Fused/Spiro Heterocyclic Compound Incorporating Quinone Compounds,” Journal of the Chinese Chemical Society, Vol. 49, 2002, pp. 387- 696.
N. A. A. Elkanzi, A. K. Khalafallah and M. Younis, “Effect of Iodine on the Antimicrobial Activity of New Spiro and Isolated β-Lactam Thiazolidinone Derivatives,” Phosphorus, Sulfur and Silicon, Vol. 182, 2007, pp. 1163-1181.