58298-68-3Relevant articles and documents
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.
Improved synthetic route to C-ring ester-functionalized prodigiosenes
Uddin, Md. Imam,Thirumalairajan, Srinath,Crawford, Sarah M.,Cameron, T. Stanley,Thompson, Alison
supporting information; experimental part, p. 2561 - 2564 (2010/11/19)
An efficient, optimized, and scalable process for the synthesis of C-ring ester-functionalized prodigiosenes has been developed by (i) exploiting a silylative Mukaiyama aldol strategy for the condensation of alkyl 5-formyl-2,4-dimethylpyrrole-3-carboxylate and 4-methoxy-3-pyrrolin-2-one to form the corresponding ester-functionalized dipyrrinone analogues, and (ii) developing a facile synthesis of stable bromodipyrrin analogues for the use in formal Suzuki coupling reactions. The process was applied to the synthesis of three C-ring ester-functionalized prodigiosenes in multigram scales (up to 6.5 g prodigiosene free-base) with useful yields (35-56% overall yields over three steps starting from the 2-formyl pyrroles). Georg Thieme Verlag Stuttgart New York.
