Synthesis of annelated analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442) using 1, 3-oxazine-2, 4 (3 H)-diones as key intermediates

…, L Christensen, G Ludvig, PT Jørgensen…

Index: Larsen, Janus S.; Christensen, Lene; Ludvig, Gitte; Jorgensen, Per T.; Pedersen, Erik B.; Nielsen, Claus Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 18 p. 3035 - 3038

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Citation Number: 15

Abstract

Condensation of ethyl 3-phenyl-2-oxocyclopentanecarboxylate 5 with 2-(S-methylthio) isourea followed by hydrolysis with HCl gave 6, 7-dihydro-7-phenylcyclopenta [e][1, 3] oxazine-2, 4 (3 H, 5 H [hair space])-dione (10a). 7, 8-Dihydro-8-phenyl-6 H-cyclohexa [e][1, 3] oxazine-2, 4 (3 H, 5 H [hair space])-dione (10b) was synthesised by reacting 2- phenylcyclohexanone (9b) with N-(chlorocarbonyl) isocyanate. The oxazines 10a, b were ...