Holshouser M H, Loeffler L J
J Pharm Sci. 1982 Jun;71(6):715-7. doi: 10.1002/jps.2600710630.
Treatment of thiochroman-4-one-1,1-dioxide (II) with paraformaldehyde and dimethylamine hydrochloride in isopropyl alcohol at reflux afforded directly in 80% yield the dimeric dihydropyran (IV), corresponding to the dimerization of the target compound 3-methenyl-thiochroman-4-one-1,1-dioxide (III). Neither the monomer III nor the expected Mannich base, 3-dimethylaminomethylthiochroman-4-one-1,1-dioxide, were isolated under conditions of the reaction. The monomer III could be prepared in 55% yield by sublimation of the dimer IV at 230-250 degrees; however, redimerization slowly occurred at room temperature. The dimer IV was also prepared by the use of paraformaldehyde and N-methylanilinium trifluoroacetate. The monomer III was found to be marginally active at 10 mg/kg/day versus Ehrlich ascites tumor growth in mice.
在异丙醇中，将硫代色满-4-酮-1,1-二氧化物（II）与多聚甲醛和盐酸二甲胺一起回流处理，以80%的产率直接得到二聚二氢吡喃（IV），这相当于目标化合物3-亚甲基-硫代色满-4-酮-1,1-二氧化物（III）的二聚化。在反应条件下，既没有分离出单体III，也没有分离出预期的曼尼希碱3-二甲基氨基甲基硫代色满-4-酮-1,1-二氧化物。通过在230 - 250℃升华二聚体IV，可以55%的产率制备单体III；然而，在室温下会缓慢地发生再二聚化。二聚体IV也可通过使用多聚甲醛和三氟乙酸N-甲基苯胺盐来制备。发现单体III在以10mg/kg/天的剂量时，对小鼠艾氏腹水瘤的生长仅有微弱活性。
