Synthesis of some Heterocyclic Compounds Derived from 2-Chloro-N-p-Tolylacetamide
DOI:
https://doi.org/10.23851/mjs.v27i4.26Keywords:
Hetroylic, p-aminotoluene, aromaticaldehydes, Sshiff bass, β-lactamAbstract
This research includes preparation of (2-chloro-N-p-tolylacetamide) (1) from the reaction of (p-aminotoluene) with chloro acetyl chloride. Compound (1) reacted with thiosemi carbazide and gave compound (2), and when compound (1) reacted with semicarbazide gave compound (3). While when compound (1) reacted with thiourea it produced compound (4).
Compounds (2-4) when reacted with appropriate aromatic aldehydes or ketones produced Shiff bass (5-16), which in turn reacted with chloro acetyl chloride in the present of tri ethyl amine and dioxin gave β-lactam derivatives (14-22). The structures of these compounds were characterized from their melting points, FT-IR, and NMR.
Downloads
References
Palmer D.C.,VenkatramanS.,``The Chemistry of heterocyclic compound oxazoles: synthesis , reactions and spectroscopy`` Part A Ed., Weily& Sons, Hoboken, NJ , USA , 60:1-390,2003.
KuniedaT.,MatsunagaH.``The chemistry of heterocyclic compound, oxazoles : synthesis , reactions and spectroscopy`` Part B Ed.,Palmer D.C., Wiley & sons : Hobken , NJ, USA , 60 :1-52,2004.
Jin Z.``Imidazole,oxazole and thiazolealkoides``Nat.Prod.Rep.,23:364-496, 2006.
Yeh VSC ``Recent advances in the total synthesis of oxazole containing natural product`` Tetrahedron,60:11995-12042,2004.
Rawal RK, TripathiR,KattiSB,PanneCouque C, De Clercq and E.Design``Synthesis and evaluation of 2-aryl-3- hetero aryl-1,3-thiazolidine-4-ones as anti-HIV agents.Bioorg.Med.Chem.;15(4):1725-31,2007.
DabholkarVijoy V.;Sayad S.Ahmed.,Ind.J. of heterocyclic Chem.20:171-172, 2010.
Beale J. M., Block J.H., Wilson`s and Gisvold`s Textbook of Organic Medicinal and pharmaceutical Chemistry,12th Ed. ,Lippincott , Williams and Wilkins, Philadelphia,281:324-349,2011.
Shai A.A., Raghuwanshi M.G., Khurshid I., MolviSayyedNazim and Aeyaz Ahmed ``Schiff`s Bases and Amides of Selected Five Membered Heterocyclic compounds`` J. Chem. Pharm. Res.,5(6):14-25,2013.
Chu D.T.W., Plattner J.J. and Kat Z.`` New Direction in Antibacterial Research`` J.Med.Chem.,39:3853,1996.
Southgate R.,Contemp.Org.Synth.,1:417,1994.
De KimpeN.``In comprehensive heterocyclic chemistry II, `` Padwa A., Ed.,Elsevier:Oxford,UK,536,1996.
Burnett D.A.,Caplen,M.A.,Davis,H.R.Jr.Burrie,R.e. &Clader J.W.``2-Azeto -nes as Inhibitors and Cholestrol Absorption``J.Med.Chem.37:1733, 1994.
Han W.T.,Trehan a.K.,wright J.j.,FedericiM.E.Seilder S.M. and Meanwell N.A.``Azetidin-2-one Derivatives as Inhibitors of Thrombin`` Bio.Org. Med. Chem.,3:1123,1995.
Smith D.M.,KaziA.,SmithL.,Long T.E.,Helderth B.,TurosE.and Dou Q.P.``Novel β-Lactam Antibiotic ActivatesTumer Cell Apoptotic program by Inducing DNA Damage`` Mol.Pharmacol.,61:1348,2002.
Shah S/H.PatelP.S.``Synthesis and Antimicrobial Activity of Azetidin-2-One Containing Pyrazoline Derivatives``Res.J.Chem.Sci.,2(7)62,2012.
Ram S.Prasad,SaraSwathyT.,Niraimathi V.,Indhumathi B. ``Synthesis, Characterization and Antimicrobial Activity of Some of the Benzocaine Derivatives`` Int.J.Pharm. Sci.4(5):285-287,2012.
MadaS.,Arora R.,VenagoOpalanP.,Ban S.S.``Tetrahedron``Lett.,41:5577, 2000.

Downloads
Key Dates
Received
Accepted
Published
Issue
Section
License
Copyright (c) 2017 Al-Mustansiriyah Journal of Science

This work is licensed under a Creative Commons Attribution 4.0 International License.
(Starting May 5, 2024) Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution (CC-BY) 4.0 License that allows others to share the work with an acknowledgement of the work’s authorship and initial publication in this journal.