Synthesis of Coumarines and 4H-Chromenes through the Reaction of tert-Butyl Isocyanide and Dialkyl Acetylenedicarboxylates in Presence of 2-Hydroxybenzaldehydes

Issa Yavari; Hoorieh Djahaniani; Farough Nasiri

doi:10.1055/s-2004-815990

PAPER

Synthesis of Coumarines and 4H-Chromenes through the Reaction of tert-Butyl Isocyanide and Dialkyl Acetylenedicarboxylates in Presence of 2-Hydroxybenzaldehydes

Issa Yavari*, Hoorieh Djahaniani, Farough Nasiri
Department of Chemistry, University of Tarbiat Modarres, P. O. Box 14115-175, Tehran, Iran
Fax: +98(21)8006544; e-Mail: isayavar@yahoo.com;

Abstract

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Abstract

An effective route to novel coumarines and 4H-chromenes is described. This involves the reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in the presence of 2-hydroxybenzaldehydes.

Key words

4H-chromenes - coumarines - alkyl isocyanides - 2-hydroxybenzaldehyde

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Referenzen

References

<A NAME="RP09903SS-1">1</A> Ellis GP. Chromenes, Chromanones and Chromones Wiley; New York: 1971.

<A NAME="RP09903SS-2">2</A> Murray DH. Mendes J. Brown SA. The Nature of Coumarins: Occurance, Chemistry and Biochemistry Wiley; New York: 1982.

<A NAME="RP09903SS-3">3</A> Cruz-Almanza R. Perez-Flores F. Lemini C. Heterocycles 1994, 37: 795

<A NAME="RP09903SS-4">4</A> Cassidy F. Evans JM. Hadley MS. Haladiy AH. Leach PE. Stemp G. J. Med. Chem. 1992, 35: 1623

<A NAME="RP09903SS-5">5</A> Van TN. Debenedetti S. De Kimpe N. Tetrahedron Lett. 2003, 44: 4199

<A NAME="RP09903SS-6">6</A> Parker KA. Mindt TL. Org. Lett. 2001, 3: 3875

<A NAME="RP09903SS-7">7</A> Kumar P. Bodas MS. Org. Lett. 2000, 2: 3821

<A NAME="RP09903SS-8">8</A> Melini L. Adv. Heterocycl. Chem. 1975, 18: 159

<A NAME="RP09903SS-9">9</A> Hepworth JD. In Comprehensive Heterocyclic Chemistry Vol. 3: Katritzky AR. Rees CW. Pergamon; Oxford: 1984. p.573-883

<A NAME="RP09903SS-10">10</A> Davis SG. Mobbs BE. Goodwin CJ. J. Chem. Soc., Perkin Trans. 1 1987, 2597

<A NAME="RP09903SS-11">11</A> Yavari I. Adib M. Hojabri L. Tetrahedron 2001, 57: 7537

<A NAME="RP09903SS-12">12</A> Yavari I. Anary-Abbasinejad M. Alizadeh A. Hossaini Z. Tetrahedron 2003, 59: 1289

<A NAME="RP09903SS-13">13</A> Ugi I. Isonitrile Chemistry Academic Press; London: 1971.

<A NAME="RP09903SS-14">14</A> Ugi I. Angew. Chem., Int. Ed. Engl. 1982, 21: 810

<A NAME="RP09903SS-15">15</A> Domling A. Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3168

<A NAME="RP09903SS-16">16</A> Walborsky HM. Periasamy MP. In The Chemistry of Functional Groups, Supplement C Patai S. Rappoport Z. Wiley; New York: 1983. Chap. 20. p.835

<A NAME="RP09903SS-17">17</A> Marcaccini S. Torroba T. Org. Prep. Proced. Int. 1993, 25: 141