Synthesis of Polyfunctionalized Pyrroles by a PPh3-Promoted Condensation Reaction Between Ammonium Acetate, Dialkyl Acetylenedicarboxylate and Arylglyoxals

Document Type : Research Note

Authors

Department of Chemistry, Mahshahr Branch, Islamic Azad University, Mahshahr, I.R. IRAN

Abstract

A simple and efficient synthesis of some polyfunctionalized pyrrole derivatives by a triphenylphosphine-promoted condensation reaction between dialkyl acetylenedicarboxylates, arylglyoxals, and ammonium acetate is described. This present  method carries several advantages, such as good yields, a simple procedure, non-hazardous reaction conditions and starting from easily accessible substrates

Keywords

Main Subjects

References

[1] Gribble G.W., In: “Comprehensive Heterocyclic Chemistry I”I, Vol. 2; Katriztky A. R., Rees C. W., Scriven E. F. V., Eds., Elsevier: Oxford, 207(1996).
[2]Jones R.A., Bean G.P., “The Chemistry of Pyrroles”; Academic Press: London, 1(1977).[3] Bean G.P., In: “The Chemistry of Heterocyclic Compounds”; Jones A. R. Ed.; Wiley: New York, Vol. 48, Part 1, Chapter 2, p 105(1990).
[4] (a) Fan H., Peng J., Hamann M.T., Hu J.F., Lamellarins and Related Pyrrole-Derived Alkaloids From Marine Organisms, Chem. Rev., 108(1): 264-287(2008).
(b) Estevez V., Villacampa M., Menendez J.C., Multicomponent Reactions for the Synthesis of Pyrroles, Chem. Soc. Rev., 39: 4402-4421(2010).
[5] Dieter R.K., Yu H., A Facile Synthesis of Polysubstituted Pyrroles, Org. Lett., 2(15): 2283-2286 (2000).
[6] Iwasawa N., Maeyama K., Saitou M., Reactions of Propargyl Metallic Species Generated by the Addition of Alkynyllithiums to Fischer-Type Carbene Complexes, J. Am. Chem. Soc., 119(6): 1486-1487 (1997).
[7] Furstner A., Weintritt H., Hupperts, A., A New Titanium-Mediated Approach to Pyrroles: First Synthesis of Lukianol a and Lamellarin-o-Dimethyl Ether, J. Org. Chem., 60: 6637-6641(1995).
[8] Katritzky A.R., Jiang J., Steel J., 1-Aza-1,3-Bis(triphenylphosphoranylidene)propane: A Novel: CHCH2N: Synthon, J. Org. Chem., 59(16):4551-4555 (1994).
[9] Chen N., Lu Y., Cadamasetti K., Hurt C.R., Norman M.K., Fotsch C., A Short, Facile Synthesis of 5-Substituted 3-Amino-1H-pyrrole-2-carboxylates, J. Org. Chem., 65(8): 2603-2605 (2000).
[10] Bharadwaj A.R., Scheidt K.A.,Catalytic Multicomponent Synthesis of Highly Substituted Pyrroles Utilizing a One-Pot Sila-Stetter/Paal−Knorr Strategy,Org. Lett., 6(23):2465-2468 (2004).
[11] Chien T.C., Meade E.A., Hinkley J.M., Townsend L.B., Facile Synthesis of 1-Substituted 2-Amino-3-Cyanopyrroles: New Synthetic Precursors for 5,6-Unsubstituted Pyrrolo[2,3-d]Pyrimidines, Org. Lett., 6(17) :2857-2859 (2004).
[12] Nair V., Nair J.S., Vinod A.U., Rath N.P., Triphenylphosphine Promoted Addition of Dimethyl Acetylenedicarboxylate to 1, 2-Benzoquinones: Facile Synthesis of Novel γ-Spirolactones, J. Chem. Soc. Perkin Trans 1, 3129-3130 (1997).
[13]Anary-Abbasinejad M., Anaraki-Ardakani H., Hosseini-Mehdiabad H., One-Pot Synthesis of Stable Phosphorus Ylides by Three-Component Reaction between Dimethyl Acetylenedicarboxylate, Semicarbazones, and Triphenylphosphine. Phosphorus, Sulfur and Silicon, 188: 1440-1446 (2008).
[14] Yavari I., Hekmat-Shoar  R.,  Zonouzi A., A New and Efficient Route to 4-Carboxymethylcoumarins Mediated by Vinyl Tiphenylphosphonium Salt, Tetrahedron Lett, 39(16): 2391-2392 (1998).
[15] Yavari I., Adib M., Hojabri L., Vinyltriphenylphosphonium Salt Mediated Serendipitous Synthesis of Arylimin Ophosphoranes, Tetrahedron, 58:7213-7219 (2002).
[16]( a) Kamijo S., Kanazawa C., YamamotoY., Copper- or Phosphine-Catalyzed Reaction of Alkynes with Isocyanides. Regioselective Synthesis of Substituted Pyrroles Controlled by the Catalyst, J. Am. Chem. Soc, 127(25):9260–9266 (2005).
(b) Kamijo S., Kanazawa C., YamamotoY., Phosphine-Catalyzed Regioselective Heteroaromatization between Activated Alkynes and Isocyanides Leading to Pyrroles, Tetrahedron Letters, 46(52) :2563–2566 (2005).
[17] Maghsoodlou M.T., Rostami Charati F., Habibi Khorassani S.M., Khosroshahrodi M., Makha M., Synthesis of Pyrrole Phosphonate Esters: Emphasis on Pyrrole NH Acids and Dialkylacetylenic Esters Substitution, Iran. J. Chem. Chem. Eng. (IJCCE), 27(1): 105-113 (2008). 
[18] Anaraki-Ardakani H., Mosslemin M.H., Anary-Abbasinejad M., Mirhosseini S.H., Shams N., A Facile Route to the Synthesis of Polyfunctionalized Pyrroles, Arkivoc, xi: 343-349(2010).
[19] Anaraki-Ardakani H., Noei M., Tabarzad A., Facile Synthesis of N-(arylsulfonyl)-4-ethoxy-5-oxo-2,5-dihydro-1H-pyrolle-2,3-dicarboxylates by One-Pot Three-Component Reaction, Chinese Chemical Letters, 23(1):45-48(2012).
[20] Azizian J., Karimi A. R., Arefrad H., Mohammadi A.A., Mohammadizadeh M.R., A Novel One-Pot, Four Component Synthesis of Some Densely Functionalized Pyrroles, Molecular Diversity, 6: 223-226 (2003).
[21] Kassaee M.Z., Masrouri H., Movahedi F., Partovi T., One-Pot Four-Component Synthesis of Tetrasubstituted Pyrroles, Helvetica Chimica Acta,  91(2): 227-231 (2008).
[22] Azizian J., Hosseini J., Mohammadi  M. k., Sheikholeslami F., Efficient Route for the Synthesis of Highly Substituted Pyrroles, Synthetic Communications, 40(23): 3472-3479 (2010).
[23] Anaraki-Ardakani H., Hassanabadi A., Fazilnia  A ., Tabarzad A., Heidari-Rakati  T., A Facile Route to the Synthesis of 2,5-Dihydropyrrole Derivatives, Journal of Chemical Research, 38(1) 9-11(2014).
[24] Anary-Abbasinejad M., Dehghanpour-Farashah H., Hassanabadi A., Anaraki-Ardakani, H., Shams N., Three-Component Reaction of Triphenylphosphine, Dialkyl Acetylenedicarboxylate, and 2-Aminothiazole or 2-Aminobenzothiazole in the Presence of Arylglyoxals: An Efficient One-Pot Synthesis of Highly Functionalized Pyrroles, Synth. Commun., 42:1877-1884(2012).
[25] Arduengo A.J., Stewart C.A., Low Coordinate Hypervalent Phosphorus, Chem. Rev., 94, 1215-1237(1994).
[26] Yavari I., Khorramabadi-Zad A., Rashidi-Ranjbar P., Fallah-Bagher-Shaidaii H., Reaction between Trimethyl Phosphite and Dimethyl Acetylenedicarboxylate in the Presence of 5 5-Dimethylcyclohexane-1,3-Dione, J. Mol. Struct. (Theochem) 389(1):155-158 (1977).
[27] Burgada R., Leroux Y., Khoshnieh Y.O.E., Synthese et Structure d'un Trialcoxy-1,1,1 Phospholev Premier Modele Pentacoordine Contenant Le Cycle Phosphole, Tetrahedron Lett., 22:3533-3536 (1981).
[28] Cadogan J.I.G., “Organophosphorus Reagents in Organic Synthesis”, Academic Press, New York, (1979).

Files

Share

How to cite

Statistics