A. A. Harb, A. Hussein, I. Mousa
Sep 22, 2006
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Phosphorus, Sulfur, and Silicon and the Related Elements
Abstract
3-Oxo-N-{4-[(pyrimidin-2-ylamino)sulfonyl]phenyl}butanamide 1 reacts with arylidinecyanothioacetamide in refluxing ethanolic TEA to give the pyridinethione 2 rather than thiopyrane 4. Compound 2 reacts with α-haloketones to give the s-alkylated derivatives 7a–e. Compound 7a–e undergoes cyclization into thieno[2,3-b]pyridine derivatives 8a–e. The saponification of 8a gives the amino acid 9, which affords 10 when refluxed in Ac2O. The treatment of 10 with NH4OAc/AcOH gives 11. Compound II is also obtained when 8e is refluxed in Ac2O. The reaction of 8a with hydrazine hydrate gives 12 and with formamide gives 13. Compound 13 also is obtained from the reaction of 8e with triethylorthoformate. The acetylation of 8a with Ac2O gives the amide derivative 14, which, on treatment with aromatic amines, affords 15a–c. Compounds 15a–c are cyclized with H2SO4 to 16a–c. Compound 16 is obtained also from the acetylation of compound 8c, d by Ac2O. Reactions of compound 8e with CS2 in refluxing dioxane afford 17. The diazotization and self-coupling of 8e give the pyridothienotriazine 18. Finally, the chloronation of compound 13 with POCl3 affords the chloride derivative 19.