286464-95-7Relevant academic research and scientific papers
An unexpected synthesis of novel oxygen-bridged 1,5-benzothiazepine derivatives and their reductive five-membered-ring opening
Ahmad, Roshan,Zia-Ul-Haq, Mohammad,Hameed, Shahid,Akhtar, Humaira,Duddeck, Helmut
, p. 393 - 400 (2000)
A convenient procedure is reported for the preparation of benzofuro-annelated 2-phenyl-1,5-benzothiazepine derivatives by oxidative cyclocondensation of phenolic β-diketones with o-aminothiophenol in DMSO. The regiochemistry of these compounds is proven by HMBC signals and the existence of a five-bond 19F,13C-2 coupling. Surprisingly, treatment with LiAlH4 at room temperature led to a double reduction under opening of the five-membered ring. Refluxing such solutions with a higher amount of LiAlH4 gave rise to a further reduced derivative possessing the trans-configuration. All structures (regio-and stereochemistry) were assigned on the basis of NMR spectroscopic data.
