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Regioselective synthesis of new 5H,10H-dipyrimido[2,1-b:4′,5′-d][1,3]thiazine: a combined experimental and computational study

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ABSTRACT Several derivatives of the novel tricyclic system ‘dipyrimido[2,1-b:4′,5′-d][1,3]thiazine’ were synthesized via inter- and intramolecular heterocyclization of 2,4-dichloro-5-(chloromethyl)-6-methylpyrimidine and 6-amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile in short reaction times under mild conditions. An x-ray analysis… Click to show full abstract

ABSTRACT Several derivatives of the novel tricyclic system ‘dipyrimido[2,1-b:4′,5′-d][1,3]thiazine’ were synthesized via inter- and intramolecular heterocyclization of 2,4-dichloro-5-(chloromethyl)-6-methylpyrimidine and 6-amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile in short reaction times under mild conditions. An x-ray analysis together with computational calculations was performed to gain an in-depth understanding of regioselectivity of the reaction. GRAPHICAL ABSTRACT

Keywords: synthesis new; thiazine; dipyrimido thiazine; 10h dipyrimido; new 10h; regioselective synthesis

Journal Title: Journal of Sulfur Chemistry
Year Published: 2019

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