Synthesis of some Heterocyclic Compounds Derived from 2-Chloro-N-p-Tolylacetamide

Authors

  • Hanan Gh Shaaban Department of Chemistry, College of Science, Al-Mustansiriyah University, Iraq.

DOI:

https://doi.org/10.23851/mjs.v27i4.26

Keywords:

Hetroylic, p-aminotoluene, aromaticaldehydes, Sshiff bass, β-lactam

Abstract

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

Download data is not yet available.

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

Published

26-02-2017

Issue

Section

Original Article

How to Cite

[1]
H. G. Shaaban, “Synthesis of some Heterocyclic Compounds Derived from 2-Chloro-N-p-Tolylacetamide”, Al-Mustansiriyah Journal of Science, vol. 27, no. 4, Feb. 2017, doi: 10.23851/mjs.v27i4.26.

Similar Articles

1-10 of 16

You may also start an advanced similarity search for this article.