STUDIES ON THIAZOLOPYRIDINES. PART 5: SYNTHESIS OF HITHERTO UNKNOWN THIAZOLINONE AND THIAZOLO[3,2-a]PYRIDINE DERIVATIVES HAVING IN THEIR STRUCTURE THE MORPHOLIN-4-YL MOIETY

Abstract

Condensation of thiazolinone 1 with benzaldehydes 2a, b in ethanolic piperidine afforded the methylidene derivatives 3a, b. Cyclocondensation of compound 3b with malononitrile furnished the novel thiazolo[3,2-a]-pyridine 5. Also, compound 3b was condensed with dimethylformamide-dimethylacetal (DMF-DMA) and triethylortho-formate to yield N,N-dimethylamino 6 and ethoxymethylene 7 derivatives respectively. The novel thiazolo[3,2-a]pyridines 10a, b were obtained by cyclocondensation of compounds 3a, b with benzylidene-malononitriles 8a, b. Similarly, cyclocondensation of compound 3b with benzylidenemalononitrile 11 afforded the thiazolopyridines 12a–c. Ternary condensation of compound (12), 4-morpholinobenzaldehyde 2b and malononitrile (1:1:1 molar ratio) produced the thiazolopyridines 14a–c. When compound 10b was subjected to react with malononitrile in dioxane/piperidine under reflux the novel condensed heterocyclic system 18 was obtained. Treatment of ortho-aminocarbonitrile 10b with formic acid, aromatic aldehyde and triethylorthoformate furnished the thiazolo[2′,3′:1,6] pyrido[2,3-d] pyrimidine 20, azomethine 21a, b and ethoxymethylene 22 derivatives respectively. The structure of the synthesized compounds was established by analytical and spectral data.

Keywords:

• Condensed thiazole derivatives
• morpholine
• thiazoline
• thiazolo[3,2-a]pyridine