Synthesis of Novel N-Substituted
2-(Hetero)arylimino-1,3-thiazolidin-4-ones

Germain Revelant; Stéphanie Hesse; Gilbert Kirsch

doi:10.1055/s-0030-1257867

PAPER

Synthesis of Novel N-Substituted 2-(Hetero)arylimino-1,3-thiazolidin-4-ones

Germain Revelant, Stéphanie Hesse*, Gilbert Kirsch
Laboratoire d’Ingénierie Moléculaire et Biochimie Pharmacologique, Institut Jean Barriol, FR CNRS 2843, 1 Boulevard Arago, 57070 Metz, France
Fax: +33(3)87325801; e-Mail: hesse@univ-metz.fr;

Abstract

All articles of this category

Abstract

The preparation of new N-substituted 2-arylimino-1,3-thiazolidin-4-ones from 5-substituted-3-aminothiophenes using an easy three-step procedure is described.

Key words

5-substituted 3-aminothiophenes - isothiocyanates - thioureas - N-substituted 1,3-thiazolidin-4-ones

Full Text

References

<A NAME="RZ14110SS-1">1</A> Singh SP. Parmar SS. Raman K. Stenberg VI. Chem. Rev. 1981, 81: 175

<A NAME="RZ14110SS-2A">2a</A> Unangst PC. Connor DT. Cetenko WA. Sorenson RJ. Kostlan CR. Sircar JC. Wright CD. Schrier DJ. Dyer RD. J. Med. Chem. 1994, 37: 322

<A NAME="RZ14110SS-2B">2b</A> Johnson AR. Marletta MA. Dyer RD. Biochemistry 2001, 40: 7736

<A NAME="RZ14110SS-3">3</A> Omar K. Geronikaki A. Zoumpoulakis P. Camoutsis C. Sokovic M. Ciric C. Glamoclija J. Bioorg. Med. Chem. 2010, 18: 426

<A NAME="RZ14110SS-4A">4a</A> Vicini P. Geronikaki A. Anastasia K. Incerti M. Zani F. Bioorg. Med. Chem. 2006, 14: 3859

<A NAME="RZ14110SS-4B">4b</A> Vicini P. Geronikaki A. Incerti M. Zani F. Dearden J. Hewitt M. Bioorg. Med. Chem. 2008, 16: 3714

<A NAME="RZ14110SS-5A">5a</A> Najer H. Guidicelli R. Morel C. Menin J. Bull. Soc. Chim. Fr. 1963, 1018

<A NAME="RZ14110SS-5B">5b</A> Harnden MR. Wright ND. J. Chem. Soc., Perkin Trans. 1 1977, 1012

<A NAME="RZ14110SS-5C">5c</A> Sedlák M. Hejtmánková L. Hanusek J. Macháček V. J. Heterocycl. Chem. 2002, 39: 1105

<A NAME="RZ14110SS-5D">5d</A> Klika KD. Janovec L. Imrich J. Suchár G. Kristian P. Sillanpää R. Pihlaja K. Eur. J. Chem. 2002, 1248

<A NAME="RZ14110SS-5E">5e</A> St.Laurent DR. Gao Q. Wu D. Serrano-Wu MH. Tetrahedron Lett. 2004, 45: 1907

<A NAME="RZ14110SS-6">6</A> Majcen le Maréchal A. Robert A. Leban I. Tetrahedron 1990, 46: 453

<A NAME="RZ14110SS-7">7</A> Blanchet J. Zhu Z. Tetrahedron Lett. 2004, 45: 4449

<A NAME="RZ14110SS-8A">8a</A> Thomae D. Perspicace E. Henryon D. Xu Z. Schneider S. Hesse S. Kirsch G. Seck P. Tetrahedron 2009, 65: 10453

<A NAME="RZ14110SS-8B">8b</A> Hesse S. Perspicace E. Kirsch G. Tetrahedron Lett. 2007, 48: 5261

<A NAME="RZ14110SS-8C">8c</A> Thomae D. Kirsch G. Seck P. Synthesis 2007, 2153

<A NAME="RZ14110SS-9">9</A> Abdillahi A. Revelant G. Datoussaid Y. Kirsch G. Synthesis 2010, 2543 and references cited therein for the synthesis of 3-aminothiophenes

<A NAME="RZ14110SS-10">10</A> Santagati A. Longmore J. Guccione S. Langer T. Tonnel E. Modica M. Santagati M. Monsù Scolaro L. Russo F. Eur. J. Med. Chem. 1997, 32: 973

<A NAME="RZ14110SS-11">11</A> Zhou H. Wu S. Zhai S. Liu A. Sun Y. Li R. Zhang Y. Ekins S. Swaan PW. Fang B. Zhang B. Yan B.
J. Med. Chem. 2008, 51: 1242

<A NAME="RZ14110SS-12">12</A> Mandhare PN. Rindhe SS. Patil LR. Mane RA. Indian J. Heterocycl. Chem. 2003, 12: 209

<A NAME="RZ14110SS-13">13</A> Ottana R. Maccari R. Barreca ML. Bruno G. Rotondo A. Rossi A. Chiricosta G. Di Paola R. Sautebin L. Cuzzocrea S. Vigorita MG. Bioorg. Med. Chem. 2005, 13: 4243

<A NAME="RZ14110SS-14">14</A> Abdillahi I. Kirsch G. Synthesis 2010, 1428