Synthesis of Thiophene Derivatives on Soluble Polymer-Support Using Gewald Reaction

Haiqing Zhang; Guichun Yang; Jianian Chen; Zuxing Chen

doi:10.1055/s-2004-834895

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Synthesis of Thiophene Derivatives on Soluble Polymer-Support Using Gewald Reaction

Haiqing Zhang, Guichun Yang*, Jianian Chen, Zuxing Chen
Faculty of Chemistry and Material Science, Hubei University, Wuhan, Hubei, 430062, P. R. China
e-Mail: +86(27)88663043; e-Mail: ygc33@163.net;

Abstract

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Abstract

A variety of thiophene derivatives have been synthesized using poly(ethylene glycol) (PEG) as soluble polymer support. PEG reacted with cyanoacetic acid, DCC and DMAP in CHCl₃ under microwave irradiation to give PEG-bound cyanoacetic ester 1. A mixture of 1, elemental sulfur, DIPEA and 2 carried out Gewald reaction under microwave irradiation to afford 3, which was acylated and treated with 1% KCN in methanol to give thiophene derivatives 6. This synthetic method is simple and mild, and the yields are moderate to high.

Key words

thiophene derivatives - synthesis - Gewald reaction - soluble polymer-support - microwave

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References

<A NAME="RF07204SS-1">1</A> Pinto IL. Jarvest RL. Serafinowska HT. Tetrahedron Lett. 2000, 41: 1597

<A NAME="RF07204SS-2">2</A> Sabnis RW. Rangnekar DW. Sonawane ND. J. Heterocycl. Chem. 1999, 36: 333

<A NAME="RF07204SS-3">3</A> Koike K. Jia Z. Nikaido T. Liu Y. Zhao Y. Guo D. Org. Lett. 1999, 1: 197

<A NAME="RF07204SS-4">4</A> Gutschow M. Kuerschner L. Neumann U. Peitsch M. Loser R. Kolglin N. Eger K. J. Med. Chem. 1999, 42: 5437

<A NAME="RF07204SS-5">5</A> Moller KB. Moller NPH. J. Biol. Chem. 2000, 275: 10300

<A NAME="RF07204SS-6">6</A> Fujita M. Hirayama T. Ikeda N. Bioorg. Med. Chem. 2002, 10: 3113

<A NAME="RF07204SS-7">7</A> Modica M. Santiagati M. Russo F. Parotti L. Gioia LD. Selvaggini M. Mennini T. J. Med. Chem. 1997, 40: 574

<A NAME="RF07204SS-8">8</A> Webb TR. Melman N. Lvovskiy D. Ji X.-D. Jacobson KA. Bioorg. Med. Chem. Lett. 2000, 10: 31

<A NAME="RF07204SS-9">9</A> Gewald K. Angew. Chem. 1961, 73: 114

<A NAME="RF07204SS-10">10</A> Mckibben BP. Cartwright CH. Castelhano AL. Tetrahedron Lett. 1999, 40: 5471

<A NAME="RF07204SS-11">11</A> Castanedo GM. Sutherlin DP. Tetrahedron Lett. 2001, 42: 7181

<A NAME="RF07204SS-12">12</A> Hoener APF. Henkel B. Gauvin JC. Synlett 2003, 63

<A NAME="RF07204SS-13">13</A> Wentworth J. Janda KD. Chem. Commun. 1999, 1917

<A NAME="RF07204SS-14">14</A> Parrick HY. Kim DJ. Acc. Chem. Res. 2000, 33: 546

<A NAME="RF07204SS-15">15</A> Harris JH. Liu Y. Chai S. Andrews MD. Vederas JC. J. Org. Chem. 1998, 63: 2407

<A NAME="RF07204SS-16">16</A> Ranu BC. Guchhait SK. Ghosh K. Patre A. Green Chem. 2000, 2: 5

<A NAME="RF07204SS-17">17</A> Loupy A. Perreux L. Tetrahedron 2001, 57: 9199

<A NAME="RF07204SS-18">18</A> Lidstrom P. Tierney J. Wathey B. Westman J. Tetrahedron 2001, 57: 9225

<A NAME="RF07204SS-19">19</A> Chen ZX. Yang GC. Zhang ZJ. Wang D. Synthesis 2001, 1483

<A NAME="RF07204SS-20">20</A> Yang GC. Chen ZX. Zhang ZJ. React. Funct. Polym. 2002, 51: 1

<A NAME="RF07204SS-21">21</A> Chen ZX. Yue GZ. Lu CF. Yang GC. Synlett 2004, 1231