68464-72-2Relevant academic research and scientific papers
One-pot synthesis of highly substituted n -fused heteroaromatic bicycles from azole aldehydes
Outlaw, Victor K.,Dandrea, Felipe B.,Townsend, Craig A.
, p. 1822 - 1825 (2015)
An efficient route to substituted N-fused aromatic heterocycles, including indolizines, imidazo[1,2-a]pyridines, and imidazo[1,5-a]pyridines from azole aldehydes, is reported. Wittig olefination of the aldehydes with fumaronitrile and triethylphosphine affords predominantly E-alkenes that undergo rapid cyclization upon treatment with a mild base. Substituent control of the 1-, 2-, and 3-positions of the resulting heteroaromatic bicycles is shown. Alternatively, the isolable E-alkene undergoes selective alkylation with electrophiles, followed by in situ annulation to indolizines additionally substituted at the 6-position.
