1027223-95-5Relevant academic research and scientific papers
Synthesis of thieno-fused heterocycles through reiterative iodocyclization
Aurelio, Luigi,Volpe, Rohan,Halim, Rosliana,Scammells, Peter J.,Flynn, Bernard L.
, p. 1974 - 1978 (2014)
Iodocyclization of ethynyl methyl sulfides gives 3-iodo-2-thiomethyl heterocycles, setting up the synthesis of thieno-fused systems through a subsequent iteration of alkyne coupling and iodocylization. This approach can also be exploited in the synthesis of polyfused thiophenes. In developing this protocol it was necessary to address issues associated with unfavourable electronic bias and redox sensitivity in some substrates. The manner in which these have been addressed should prove useful elsewhere in iodocyclization chemisty.
Scaffold-divergent synthesis of ring-fused indoles, quinolines, and quinolones via iodonium-induced reaction cascades
Halim, Rosliana,Aurelio, Luigi,Scammells, Peter J.,Flynn, Bernard L.
, p. 4708 - 4718 (2013/06/27)
N-(2-Iodophenyl)imines A are readily formed from Schiff's base condensation of 2-iodoanilines with carbonyls and ketals. These imines provide useful substrates in scaffold-divergent synthesis through the attachment of an alkyne (Songashira coupling or acyl substitution of a Weinreb amide) followed by an iodonium-induced reaction cascade to give ring-fused indoles B, quinolines C, or quinolones D depending on the reaction conditions employed.
Alternating lodonium-mediated reaction cascades giving indole- And quinoline-containing polycycles
Halim, Rosliana,Scammells, Peter J.,Flynn, Bernard L.
supporting information; experimental part, p. 1967 - 1970 (2009/04/10)
A simple two-step convergent protocol gives direct access to synthetic Intermediate A from ortho-iodoanilines. Intermediate A can be treated with NIS In CH2CI2 to Induce novel lodonium mediated domino reaction cascade, which provides direct access to ring-fused Indole compounds B. Simply by changing the reaction conditions, this protocol can be directed down an alternative domino reaction cascade to give various ring fused quinoline compounds C.
