Cyclotrimerization of Enaminones: An Efficient Method for the Synthesis of 1,3,5-Triaroylbenzenes

Ibrahim Elghamry

doi:10.1055/s-2003-41056

SHORTPAPER

Cyclotrimerization of Enaminones: An Efficient Method for the Synthesis of 1,3,5-Triaroylbenzenes

Ibrahim Elghamry*
Institute of Organic Chemistry, Georg-August University, Tammannstr. 2, 37077 Göttingen, Germany
Fax: +49(551)399476; e-Mail: ielgham@gwdg.de;

Abstract

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Abstract

An efficient method for the synthesis of 1,3,5-triaroylbenzenes 2a-f by cyclotrimerization of enaminones 1a-f in acetic acid/pyridine (4:1) is illustrated. The structures of the products have been delineated by spectroscopic methods.

Keywords

cyclotrimerization - enaminones - triaroylbenzenes - supramolecular chemistry - regioselectivity

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References

<A NAME="RZ08803SS-1">1</A> Pigge CF. Ghsedi F. Tetrahedron Lett. 2000, 41: 6545

<A NAME="RZ08803SS-2">2</A> Pigge CF. Ghsedi F. Rath PN. J. Org. Chem. 2002, 67: 4547

<A NAME="RZ08803SS-3">3</A> Matsuda K. Nakamura N. Inoue K. Koga N. Iwamura H. Bull. Chem. Soc. Jpn. 1996, 69: 1483

<A NAME="RZ08803SS-4">4</A> Rose JD. Statham FS. J. Chem. Soc. 1950, 69: 69

<A NAME="RZ08803SS-5">5</A> Sasaki T. Suzuki Y. Tetrahedron Lett. 1967, 3137

<A NAME="RZ08803SS-6">6</A> Jutz C. Wagner RM. Kraatz A. Loebering HG. Annalen 1975, 874

<A NAME="RZ08803SS-7">7</A> Croxail WJ. Van Hook JO. J. Am. Chem. Soc. 1949, 71: 2442

<A NAME="RZ08803SS-8">8</A> House HO. Reif DJ. Wasson RL. J. Am. Chem. Soc. 1957, 79: 2490

<A NAME="RZ08803SS-9">9</A> Gosselck J. Schmidt G. Beress L. Schenk H. Tetrahedron Lett. 1968, 331

<A NAME="RZ08803SS-10">10</A> Murahashi S.-I. Mitsue Y. Tsumiyama T. Bull. Chem. Soc. Jpn. 1987, 60: 3285

<A NAME="RZ08803SS-11">11</A> Balasubramanian KK. Selvaraj S. Synthesis 1980, 29

<A NAME="RZ08803SS-12">12</A> Elghamry I. Synth. Commun. 2002, 32: 897

<A NAME="RZ08803SS-13">13</A> Elnagdi MH. Elghamry I. Kandeel E. Abdelrahman AH. Al-Naggar AA. Amir S. Riad M. Gazz. Chim. Ital. 1997, 127: 291

<A NAME="RZ08803SS-14">14</A> Kuckländer U. Enaminones as Synthones, In The Chemistry of Enamines Rappoport Z. John Wiley and Sons; New York: 1994. p.323-636

<A NAME="RZ08803SS-15A">15a</A> Michael PJ. Parsons AS. Tetrahedron 1996, 52: 2199

<A NAME="RZ08803SS-15B">15b</A> Michael PJ. Gravestock D. Synlett 1996, 981

<A NAME="RZ08803SS-16A">16a</A> Greenhill JV. Chem. Soc. Rev. 1977, 6: 277

<A NAME="RZ08803SS-16B">16b</A> Ping L. Greenhill JV. Enaminones in Heterocyclic Synthesis, Advances In Heterocyclic Chemistry Vol. 67: Academic Press; New York: 1997. p.203-343

<A NAME="RZ08803SS-17">17</A> 1,3,5-Tribenzoylbenzene was found as a minor product when phenyl ethynyl ketone was treated with acetic acid. For example see: Johnson AW. J. Chem. Soc. 1947, 1626