Oxazolo[3′,2′ :1,2]pyrido[3,4-<i>b</i>]indole und [1,3]-Oxazino [3′,2′ :1,2]pyrido[3,4-<i>b</i>]indole durch eine einfache Kondensationsreaktion von 3,4-Dihydro-β-carbolin mit α- bzw. β-Hydroxycarbonsäuren
作者:Klaus Th. Wanner、Ulrich Weber
DOI:10.1055/s-1994-25483
日期:——
Oxazolo[3′,2′:1,2]pyrido[3,4-b]indoles and [1,3]-Oxazino[3′,2′:1,2]-pyrido[3,4-b]indoles by a Simple Condensation Reaction of 3,4-Dihydro-β-carboline with α- and β-Hydroxycarboxylic Acids 3,4-Dihydro-β-carboline (3) is reacted with trimethylsilyloxyacyl chlorides 2a, 2b, 7 and 11 to give the 1,3-oxazolidin-4-ones 4a/5a and 4b/5b and the 1,3-oxazin-4-ones 8/9 and 12, respectively, representing a new condensation reaction. The enantiomeric purity of the compounds 4a and 5a derived from (S)-mandelic acid [(S)-1a] is found to be greater than 99.5 ee thus establishing that the procedure is compatible with chiral compounds.
Oxazolo[3′,2′:1,2]pyrido[3,4-b]indoles and [1,3]-Oxazino[3′,2′:3,4-二氢-δ-咔啉与δ-和δ-羟基羧酸的简单缩合反应 3,4-二氢-δ-咔啉(3)与三甲基硅氧烷酰氯 2a、2b、7 和 11 反应,分别得到 1,3-噁唑烷-4-酮 4a/5a 和 4b/5b,以及 1,3-噁唑烷-4-酮 8/9 和 12,这是一种新的缩合反应。从(S)-扁桃酸[(S)-1a]中得到的化合物 4a 和 5a 的对映体纯度大于 99.5 ee,从而确定了该过程与手性化合物兼容。