669763-91-1Relevant academic research and scientific papers
Smiles rearrangement for the synthesis of 5-amino-substituted [1]benzothieno[2,3-b]pyridine
Bonini, Carlo,Funicello, Maria,Scialpi, Rosanna,Spagnolo, Piero
, p. 7515 - 7520 (2003)
The Smiles rearrangement was successfully applied to 4-hydroxybenzo[b]thiophene furnishing a facile entry to the 4-amino derivative. The rearrangement was extended to 5-methoxy-4-methoxycarbonyl[1]benzothieno[2,3-b]pyridine obtained via aza-Wittig/electrocyclization reaction of novel N-(4-methoxybenzothiophen-2-yl)iminomethyldiphenylphosphorane with methyl trans-4-oxo-2-pentenoate. The preparation of a novel 5-amino-4-methoxycarbonyl[1]benzothieno[2,3-b]pyridine, which is of interest as a potential secondary peptide structure mimic, was successfully achieved.
