Solid-Phase Synthesis of Heterocycles from 1,4-Diketone Synthons [1]

Abstract

The solid-phase synthesis of furans, thiophenes, pyrroles and pyridazines from 1,4-diketones as the common intermediate is reported. A diverse collection of these heterocyclic compounds is readily prepared in two high yielding steps.

1,4-diketones - furans - pyrroles - thiophenes - pyrid­azines

References

<A NAME="RS06602ST-1">1</A>

IICT communication No. 020814

<A NAME="RS06602ST-2A">2a</A> Nefzi A. Ostresh JM. Houghten RA. Chem. Rev.  1997,  97:  449 

<A NAME="RS06602ST-2B">2b</A> Krchnak V. Holladay MW. Chem. Rev.  2002,  102:  61 

<A NAME="RS06602ST-3">3</A> Raghavan S. Anuradha K. Tetrahedron Lett.  2002,  43:  5181 

For earlier reports on the solid-phase synthesis of furans refer:

<A NAME="RS06602ST-4A">4a</A> Gowravaram MR. Gallop MA. Tetrahedron Lett.  1996,  37:  6973 

<A NAME="RS06602ST-4B">4b</A> Whitehouse DL. Nelson KH. Savinov SN. Austin DJ. Tetrahedron Lett.  1997,  38:  7139 

<A NAME="RS06602ST-4C">4c</A> Han Y. Roy A. Giroux A. Tetrahedron Lett.  2000,  41:  5447 

<A NAME="RS06602ST-5">5</A> For an earlier report on the solid-phase synthesis of thiophene refer: Han Y. Giroux A. Lepine C. Laliberte F. Huang Z. Perrier H. Bayly C. Young R. Tetrahedron  1999,  55:  11669 

<A NAME="RS06602ST-6">6</A> For an earlier report on the solid-phase synthesis of pyrroles refer: Mjalli AMM. Toyonaga BE. In Molecular Diversity and Combinatorial Chemistry: Libraries and Drug Discovery   Chaiken IM. Janda KD. American Chemical Society; Washington DC: 1996.  p.70 

<A NAME="RS06602ST-7">7</A> Friedrischsen W. Pagel K. Prog. Heterocycl. Chem.  1995,  7:  130 

<A NAME="RS06602ST-8A">8a</A> Di Santo R. Costi R. Artico M. Massa S. Lampis G. Deidda D. Rompei R. Biorog. Med. Chem. Lett.  1998,  8:  2931 

<A NAME="RS06602ST-8B">8b</A> Ragno R. Marshall GR. Di Santo R. Costi R. Massa S. Rompei R. Artico M. Bioorg. Med. Chem.  2000,  8:  1423 

<A NAME="RS06602ST-9A">9a</A> Saltiel E. Ward A. Drugs  1987,  34:  222 

<A NAME="RS06602ST-9B">9b</A> Aubert D, Ferrand C, and Maffrand JP. inventors; EP  99802.  ; Chem. Abstr. 1984, 100, 191856z

<A NAME="RS06602ST-10A">10a</A> Frank H. Heinisch G. Pharmacologically active pyridazines Part I. In Progress in medicinal chemistry   Ellis GP. West GB. Elsevier; Amsterdam: 1990.  Vol. 27.

<A NAME="RS06602ST-10B">10b</A> Curran WV. Ross A. J. Med. Chem.  1974,  17:  273 

<A NAME="RS06602ST-11">11</A> Drewes SE. Hogan CJ. Synth. Commun.  1989,  19:  2101 

<A NAME="RS06602ST-12">12</A> Brain CT. Brunton SA. Synlett  2001,  382 

<A NAME="RS06602ST-13">13</A> Shridhar DR. Jogibhukta M. Shantan Rao P. Handa VK. Synthesis  1982,  1061 

<A NAME="RS06602ST-14">14</A> Demir AS. Akmedov IM. Sesenouglu O. Alpturk O. Apaydm S. Gercek Z. Ibrahimzade N. J. Chem. Soc., Perkin Trans. 1  2001,  1162 ; and references cited therein

<A NAME="RS06602ST-15">15</A> Stetter H. Friederich J. Chem. Ber.  1981,  114:  564