A SIMPLE SYNTHESIS OF 4-HYDROXY-3,4-DIHYDROPYRIDO[3,4-d]PYRIMIDINE-2(1H)-THIONE DERIVATIVES BY THE REACTION OF 3-ISOTHIOCYANATOPYRIDIN-4-YL KETONES WITH PRIMARY AMINES

作者：Kobayashi Kazuhiro^*; Inouchi Hiroki; Konishi Manami

来源：Heterocycles, 2014, 89(9): 2168-2176.

DOI：10.3987/COM-14-13058

• 3,4-Dihydropyrido[3,4-d]pyrimidine-2(1H)-thione
• 3-Isothiocyanatopyridin-4-yl Ketone
• 3-Aminopyridine
• Glycine
• Bromoalkylamine

The reaction of aryl(3-isothiocyanatopyridin-4-yl)methanones, prepared easily from commercially available 3-aminopyridine, with primary amines at room temperature afforded 3-substituted 4-aryl-4-hydroxy-3,4-dihydropyrido[3,4-d]pyrimidine-2(1H)-thiones in good yields. These ketones could be converted to new tricyclic heterocyclic systems, 2,3-dihydro-5H-pyrido[3,4-d]thiazolo [3,2-a]pyrimidine and 3,4-dihydro-2H,6H-pyrido [3%26apos;,4%26apos;:4,5]-pyrimido[2,1-b] [1,3]thiazine, upon treatment with 2-bromoethanamine hydrobromide and 3-bromopropaneamine hydrobromide, respectively, in the presence two equivalents of triethylamine.

• 出版日期2014-9-1