| 摘要 |
<p>Cpds. (I) and their acid addition salts, where X and Y are H, F, Cl, Br, NO2, CF3, 1-4C alkyl or alkoxy R1 and R3 are 1-6C alkyl, phenyl-(1-3C alkyl), phenyl, or phenyl substd. by chloro, fluoro, bromo, nitro, trifluoromethyl, methyl or methoxy groups R2 is H or 1-6C alkyl and only alkyl when R1 is neither alkyl nor phenylalkyl R4 is phenyl, phenyl substd. by fluoro, chloro, bromo, nitro, trifluoromethyl, methyl or methoxy groups, naphthyl, pyridyl, quinolinyl, furyl, thienyl, 2-imidazolyl or 2-thiazolyl. Antithrombotic agents. where W = -CN, -COOH, -COZ, -COO.CO.R5, -C(:NH)OR5.HA, -C(:NH)-SR5HA or -C(:NH2) OR6SO3 , Z=Halogen; R5 = 1-4C alkyl, R6 = 1-4C alkylene 15.5 g. 98% HCOOH and 34.2 g. HOAc heated 2 hrs. at 50 deg.C, 8.4 g. 2-aminoacetophenone in 110 ml. tetrahydrofuran added slowly to the cooled mixt. and the mix. left 5 days at room temp. before evapn. gave 7.6 g. O-formyl-2-formylamino-acetophenone (II) m.96-7 deg. (CHCl3/100-20 deg. petr. ether). 5.6 g. (II) added slowly to 200 ml. 0.5M diborane in tetrahydrofuran at room temp., the mixt. stirred 4 hrs., 80 ml. 5N HCl added, the mixt. evapd., basified and extd. with CHCl3 gave 3.95 g. 2-methylamino-alpha-methylbenzylamine (III) as a yellow liquid. 4.5 g. (III) and 8.5 g. Zwitter ionic imidate from cinnamide and propane sultone refluxed in 50 ml. EtOH for 6 hrs., the mixt. evapd. in vacuo, the concentrate taken up in dil. HCl, washed with Et2O and the aq. portion basified gave 7.6 g. semi-solid oil which recrystd. from dil. HCl gave 2.3 g. (I, X = Y = H; R1 = R3 = Me, R2 = H, R4 = Ph, trans-isomer) HCl m.220-1 deg.C.</p> |
