117970-36-2Relevant 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.
supporting information, p. 1822 - 1825 (2015/04/27)
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.
LITHIATION OF THE 6-DIMETHYLAMINO-1-AZAFULVENE DIMER. A VERSATILE SYNTHESIS OF 5-SUBSTITUTED PYRROLE-2-CARBOXALDEHYDES.
Muchowski, Joseph M.,Hess, Petr
, p. 777 - 780 (2007/10/02)
Metalation of the dimer 1 of 6-dimethylamino-1-azafulvene, with t-butyllithium at -15 deg C, gave the 3,8-dilithio derivate 2, which after reaction with diverse electrophilic reagents and hydrolysis, provided a wide variety of 5-substituted pyrrole-2-carboxaldehydes 5.
