pyridine-based heterocycles. synthesis of new pyrido [4,34,5]thieno[2,3-d]pyrimidines and related heterocyclespyridine-based杂环化合物。.pdfVIP

Molecules 2010, 15, 2651-2666; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Pyridine-Based Heterocycles. Synthesis of New Pyrido [4,3:4,5]thieno[2,3-d]pyrimidines and Related Heterocycles Hussein El-Kashef 1,*, Abdel-Rahman Farghaly 1, Ahmed Al-Hazmi 2, Thierry Terme 3 and Patrice Vanelle 3,* 1 Chemistry Department, Faculty of Science, Assiut University, 71516 Assiut, Egypt 2 Chemistry Department, Faculty of Science, Ibb University, Yemen 3 Laboratoire Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, Universités d’Aix-Marseille I, II et III-CNRS, UMR 6264, Laboratoire Chimie Provence, 27 Bd J. Moulin, 13385 Marseille cedex 5, France ∗ Authors to whom correspondence should be addressed; E-Mails: elkashef@.eg (H.E.-K.); patrice.vanelle@univmed.fr (P.V.). Received: 11 March 2010; in revised form: 31 March 2010 / Accepted: 6 April 2010 / Published: 12 April 2010 Abstract: The synthesis of the title compounds was achieved using ethyl 2-amino-6- methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate (1) as starting material. The reaction of the amino ester 1 with phenylisothiocyanate in boiling ethanol afforded the thiourea derivative 5. The cyclization reactions of 5 under different reaction conditions led to different pyridothienopyrimidine derivatives. Other reactions of the latter derivatives leading to pyrido[4,3:4,5]thieno[2,3-d]triazolo[1,5-a]pyrimidines are also presented. Keywords: pyrimidines