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World Journal of Organic Chemistry
ISSN (Print): 2372-2150 ISSN (Online): 2372-2169 Website: https://www.sciepub.com/journal/wjoc Editor-in-chief: Subrata Shaw
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World Journal of Organic Chemistry. 2013, 1(2), 24-51
DOI: 10.12691/wjoc-1-2-4
Open AccessReview Article

Short Review on Synthesis of Thiazolidinone and β-Lactam

N. A. A. Elkanzi1, 2,

1Chemistry Department, Aswan-Faculty of Science, Aswan University, Aswan, Egypt

2Chemistry Department, Faculty of Science, Al Jouf University, Al Jouf, Kingdom of Saudi Arabia

Pub. Date: September 25, 2013
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Cite this paper:
N. A. A. Elkanzi. Short Review on Synthesis of Thiazolidinone and β-Lactam. World Journal of Organic Chemistry. 2013; 1(2):24-51. doi: 10.12691/wjoc-1-2-4

Abstract

The review summarizes literature dealing with the synthesis of thiazolidinoneand β-lactamVarious methods for synthesis of thiazolidinone and β-lactamare discussed. Like boiling benzene thioglycolic acid was added to (1)a-d using a water separator to give thiazolidinone derivatives (2)a-d. Also Reaction of the Schiff bases of 3 and /or5 with one mole of thioglycolic acid was proceeded smoothly to afford the corresponding thiazolidinone derivatives 6,7 respectively. The synthesis of a new type of compound, 2-hydrazolyl-5,5-diphenyl-4-thiazolidinone (24), obtained by treatment of thiosemicarbazone with benzyl in basic media. β-lactams were prepared by N-Tosyl-3-halo-3-butenylamines underwent efficient Ullmann-type coupling to afford 2-alkylideneazetidines, which could be readily converted to the corresponding β-lactams by oxidation with O3 to give β-lactams 119. A chiral N-heterocyclic carbene catalyzed the Staudinger reaction of arylalkylketenes with a variety of N-tert-butoxycarbonylarylimines to give the corresponding cis-β-lactams 124.

Keywords:
thiazolidinoneβ-lactamthioglycolic acidSchiffs bases synthesiscondensation

Creative CommonsThis work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

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References:

[1]  Southgate,R. Contemp. Org. Synth. 1994, 1, 417-431.
 
[2]  Broccolo, F.; Carnally, G.; Caltabiano, G.; Cocuzza, C.E.A.; Fortuna, C.; Galletti, G.; Giacomini, P.D.; Musumarra, G.; Musumeci, R.; Quitavalla, J. Med. Chem. 2006, 49, 2804-2811.
 
[3]  Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437-4492.
 
[4]  Alcaide, B.; Almendros, P. Curr. Med. Chem. 2004, 11, 1921-1949.
 
[5]  Deshmukh, A.R.A.S.; Bhawal, B.M.; Krishnaswamy, D.; Govande, V.V.; Shinkre, B.A.; Jayanthi, A.. Curr. Med. Chem. 2004, 11, 1889-1920.
 
[6]  Alcaide, B.; Almendros, P. Synlett 2002, 381-393.
 
[7]  Palomo, C.; Aizpurua, J.M.; Ganboa, I.; Oiarbide, M Synlett 2001, 1813-1826.
 
[8]  Ojima, I. The Organic Chemistry of β-Lactams; Georg, G.I., Ed.; VCH: New York, NY, USA, 1993; pp. 197-255.
 
[9]  Ojima, I. Acc. Chem. Res. 1995, 28, 383-389.
 
[10]  O’Driscoll, M.; Greenhalgh, K.; Young, A.; Turos, E.; Dickey, S.; Lim, D.V. Bioorg. Med. Chem. 2008, 16, 7832-7837.
 
[11]  Turos, E.; Reddy, G.S.K.; Greenhalgh, K.; Ramaraju, P.; Abeylath, S.C.; Jang, S.; Dickey, S.; Lim, D.V. Bioorg. Med. Chem. Lett. 2007, 17, 3468-3472.
 
[12]  Dugar, S.; Yumibe, N.; Clader, J.W.; Vizziano, M.; Huie, K.; van Heek, M.; Compton, D.S.; Davis, H.R., J. Bioorg. Med.Chem. Lett. 1996, 6, 1271-1274.
 
[13]  Han, W.T.; Trehan, A.K.; Wright, J.J.K.; Federici, M.E.; Seiler, S.M.; Meanwell, N.A. Bioorg. Med. Chem. 1995, 3, 1123-1143.
 
[14]  Borthwick, A.D.; Weingarte, G.; Haley, T.M.; Tomaszewski, M.; Wang, W.; Hu, Z.; Bedard, J.; Jin, H.; Yuen, L.; Mansour, T.S. Bioorg. Med. Chem. Lett. 1998, 8, 365-370.
 
[15]  Cainelli, G.; Galletti, P.; Garbisa, S.; Giacomini, D.; Sartor, L.; Quintavalla, A Bioorg. Med. Chem. 2003, 11, 5391-5399.
 
[16]  Zhou, N.E.; Guo, D.; Thomas, G.; Reddy, A.V.N.; Kaleta, J.; Purisima, E.; Menard, R.; Micetich, R.G.; Singh, R. Bioorg. Med. Chem. Lett. 2003, 13, 139-141.
 
[17]  Kazi, A.; Hill, R.; Long, T.E.; Kuhn, D.J.; Turos, E.; Dou, Q.P Biochem. Pharmacol. 2004, 67, 365-374.
 
[18]  Shetgiri N. P. andChitre, A. D. Ind. J. Chem. 2006, 45(B), 1308.
 
[19]  Omark., Geronikaki, A., Zoumpoulakis, P., Camoutsis, C., Soković, M., Ćirić A. and Glamočlija J., Bioorg. Med. Chem.2010, 18, 426.
 
[20]  Patel R. B., Desai P. S.; Desai K. R. and Chikhalia K. H., Indian J. Chem.. 2006, 45B, 773.
 
[21]  Turgut Z., Yolacan C., Aydogan F., Bagdatli E., Ocal N., Molecules.2007, 12, 2151.
 
[22]  Previtera T., Vigorita M. G., Bisila M., Orsini F., Benetolla F., Bombieri G., Eur. J. Med. Chem., 1994, 29, 317.
 
[23]  Srivastava S., Jain A., and Srivastav S.a, J. Indian Chem. Soc. 2006, 83, 1118.
 
[24]  Havrylyuk D., Mosula L. , Zimenkovsky B., Vasylenko O., Gzella A. and. Lesyk R. Eur. J. Med. Chem. 2010, 45(11), 5012.
 
[25]  Vigorita M. G., Ottana R., Monforte F., Maccari R., Trovato A.; Monforte M. T. and Taviano M. F., Biorg. Med.Chem.Lett2001, 11, 2791.
 
[26]  Soleiman, H.A.; Abdel-Latif, F.M; Khalil, M.A.;Elazab, 1.H., Phosphours, Sulfur and Silicon,2002,177,1001.
 
[27]  ElkanziN.A.A.; SoliemanH.A and KhalafallahA.K., Phosphorus, Sulfur, and Silicon, 2007,182: 1483-1496.
 
[28]  ElkanziN.A.A.; and KhalafallahA.K.; Abu ELhamd, H. M. and Solieman A. S., Phosphorus, Sulfur, and Silicon, 2007,182: 1483-1496.
 
[29]  Cecilia S., Chiara P., Eduardo M., Peter W. and S. Graciela S.M., Tetrahedron lett,2009, Vol.50, Issue 8. Pages 901-904.
 
[30]  MehtaPD, SengarN P.S, SubrahmanyamE V.S, SatyanarayanaD, Indian Journal of Pharmaceutical Sciences, 2006,Vol.68 Issue.1, Page 103-106.
 
[31]  Zhang L., Yue H., Wei Z., Lanping M., Jingya L., Xin W., Jia L. and JingkangS., J. Comb. Chem., 2008,10 (5), pp 632-636.
 
[32]  VagdeviHM, VaidyaVP, LathaKP, PadmashaliB, Indian Journal ofPharmaceutical Sciences,2006, Vol.68, Issue 6, pages 719-725.
 
[33]  Miller M.J., Biswas A. and Krook M.A; Tetrahedron,2008,39, 2571, 1983.
 
[34]  Kappe, C. O. "Controlled Microwave Heating in Modern Organic Synthesis", Angew. Chem. Int. Ed. 2004, 43, 6650.
 
[35]  Bin Yan,Hongyu Z.,AifengL.,XifengM.,WeiF.,WeiZ., J. Comb. Chem.,200810 (2), pp 303-312.
 
[36]  Neeraj K. F., a, Vijender S., Mohammad S. Y. and Mohammad A., ActaPoloniaePharmaceuticaDrug Research,2009, Vol. 66 No. 2 pp. 141-146.
 
[37]  SharmaM. C., SahuN. K., KohaliD. V., ChaturvediS. C., Smita. Sharma, Digest Journal of Nanomaterials and Biostructures, 2009, Vol.4, No.1,pp.223-232.
 
[38]  FerayAydogan, NüketÖcal, ZuhalTurgut, and CigdemYolacan, Bull. Korean Chem. Soc. 2001, Vol. 22, No. 5.
 
[39]  ParameswaranM.Thengungal K. RAVI G.S.Acta Pharm.2009,59, 159-170.
 
[40]  Parekh.H.H;ParikhK.A., ParikhA.R. J.ScienceIslamicRepublicof Iran,, 2004 ;15(2), 143-148.
 
[41]  Mahmoud M. B., AmanyS.M., Mogeda.H., Andreas R., Omar A. M. F., Arch Pharm Res,2005,Vol 28, No 9, 1002-1012.
 
[42]  PatelJ., Miatry BD., Desai KP, Indian J. of chemistry2008,vol. 47B,,pp.1695-1700.
 
[43]  Desai KG, Desai KR J Sulfur Chemistry; 2006,27(4): 315-328.
 
[44]  Aysel G., Nalan T., Turk J Chem.,2005, 29, , 247 -254.
 
[45]  Altinas H.,Ozonum A., SeherB., IrieksozMoltem U.D.S., GultenOtUk, TurkJ.Chem.,2005,29,425-235.
 
[46]  Zuhal Turgot, CigdemYolacan, FerayAydogan, EmineBagdatli andNuketOcal, Molec.,2007.
 
[47]  TumulS., Anil K. GaikwadW., SudhirSinha, and Setu B. K., ARKIVOC,2005,(ii) 120-130,2005.
 
[48]  patelK.H.,.MehtaA.GE-Journal of Chemistry,2006,Vol. 3, No.2, pp 103-109.
 
[49]  CandeiasN. R., GoisP. M. P., AfonsoC. A. M., J. Org. Chem.,2006, 71, 5489-5497.
 
[50]  LuH., LiC., Org. Lett,2006,8, 5365-5367.
 
[51]  A.-R. Zhang, L. He, X. Wu, P.-L. Shao, S. Ye, Org. Lett., 2008,10, 277-280.
 
[52]  LeeE. C., HodousB. L., BerginE., ShihC., FuG. C., J. Am. Chem. Soc., 2005,127, 11586-11587.
 
[53]  LinderM. R., PodlechJ., Org. Lett.,2001,3, 1849-1851.
 
[54]  Taggi, A. E., Hafez, A. M., Wack, H., Young, B., Ferraris, D. &Lectka, T.. J. Am. Chem. Soc. 2002,124, 6626-6635.
 
[55]  AmitB. and Runa P., Bioorganic & Medicinal Chemistry Letters, 15 April 2005, Vol.15, Issue 8, Pages 2015-2018.
 
[56]  Lo MCM,J Am ChemSoc,2002, 124, 4572.
 
[57]  DonatoD., StefaniaF. and Fabio P., Tetrahedron lett., 22 December 2003, Vol. 44, Issue 52, Pages 9247-9250.
 
[58]  Moshe Nahmany and ArtemMelman, J. Org. Chem., 2006, 71 (15), pp5804-5806.
 
[59]  Philip C. H. and CoreyE. J., J. Am. Chem. Soc., 2005,127 (44), pp15386-15387.
 
[60]  AliasgharJarrahpour and MaaroofZarei, Tetrahedron lett., 8 April 2009, Vol.50, Issue 14, Pages 1568-1570.
 
[61]  Yang Y., Dexuan X., Xiaoliang Z., Yongjiu L., Jie H. and Dewen D., Tetrahedron, 26 May 2008, Vol.64, Issue 22, Pages 4959-4966.
 
[62]  Anthony W., Ciby J. A., Thomas L., Org. Lett.,2005, 7 (16), pp3461-3463.
 
[63]  LuiginoT., Luisella D. V., CatiaG., TullioP.,EmanuelaP., Tetrahedron, 2 August 2004, Vol.60, Issue 32, Pages 6895-6900.
 
[64]  Elisa B., Gianfranco F., Giorgio M., Mauro P., Giovanni P.,Org. Lett., 2000,2 (8), pp 1077-1079.
 
[65]  Sharma. S. D. and SeemaKanwar, Org. Proc. Res. Dev.,2004, 8 (4), pp658-659.
 
[66]  Yan Y., Jianmei W., Margaret K., Tetrahedron Asymmetry, 4 September 2007,Vol. 18, Issue 17, Pages 2021-2029.
 
[67]  Miguel A. Sierra, M. R.F., María J. M., Luis C., Mar G.G., Tetrahedron, 29 September 2008, Vol.64, Issue 40, Pages 9592-9598.
 
[68]  Fustero S., Fernández B., Org. Lett.,2007, 9, pp. 4251-4253.
 
[69]  HiromasaKiyota, TakafumiT., Masatoshi S., Osamu N., Takayuki O.,ShigefumiKuwahara, Tetrahedron lett., 25 October 2004, Vol. 45, Issue 44,, Pages 8191-8194.
 
[70]  LuiginoT., CatiaG. and EmanuelaP., Tetrahedron, 15 December 2008, Vol. 64, Issue 51, Pages 11632-11640.
 
[71]  James H. R., JeanC. B., Patrick J. B., Stephanie R., ShyamaS., and Mary J. H., Org. Lett.,2006, 8 (14), pp 3121-3123.
 
[72]  Paula P.F., Fran O., Aisling O., Carlos G.A., Mercedes M.M, JesúsM.P. V., TeresaM. G.L., Rosario G.M.,Org. Lett.,2007, 9 (8), pp1593-1596.
 
[73]  KhallafallahA.K., ElkanziN.A.A., SoleimanH.A. and YounisM., phosphorus, sulfur and silicon, 2006,181-2483-2508.
 
[74]  Sun Joo Oh, Ki-Hoon Jung, Byung-Hyun Moon, and ChuljinAhn, Bull. Korean Chem. Soc., 2007,Vol. 28, No. 7.
 
[75]  Pablo C. Duché and Ernesto G. Mata., Molecular MedicinalChemistry, January-April 2007, vol 12, 67-69.
 
[76]  Bimal K. Banik,AnjanGhatak and Frederick F. Becker, J. Chem. Soc., Perkin Trans.2000, 1,, 2179-2181.
 
[77]  Andrew E. Taggi, A. M. Hafez, HaraldW.,Brandon Y., William J. Drury, III, and Thomas Lectka, J. Am. Chem. Soc., 2000,122, 7831-7832.
 
[78]  Zhang P.,Xu L.J. Yuan, Chinese J. Struct. Chem., 2002, Vol. 21, No. 2, 133-135.
 
[79]  Ameya A. Chavan and Nandini R. Pai, Molecules 2007, 12, 2467-2477.
 
[80]  Elaine C. Lee, Brian L. Hodous, Enda Bergin, Crystal Shih, and Gregory C. Fu, J. AM. CHEM. SOC. 2005, 127, 11586-11587.
 
[81]  Yan Yang, Fengyun Wang, Fernande D. Rochon, and Margaret M. Kayser, Can. J. Chem.,, 2005, Vol. 83, 28-36.
 
[82]  Jonathan Clayden, Stuart D. Hamilton, and Rukhsana T. Mohammed, Org. Lett, 2005,Vol. 7, No. 17,3673-3676.
 
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