1173178-79-4Relevant academic research and scientific papers
Expeditious synthesis of benzopyrans via lewis acid-catalyzed C-H functionalization: Remarkable enhancement of reactivity by an ortho substituent
Mori, Keiji,Kawasaki, Taro,Sueoka, Shosaku,Akiyama, Takahiko
supporting information; experimental part, p. 1732 - 1735 (2010/09/05)
An expeditious construction of a benzopyran skeleton via Lewis acid-catalyzed C-H functionalization was achieved. In this process, a [1,5] hydride shift and 6-endo cyclization successively occurred to give benzopyrans. The presence of substituents ortho to the alkoxy group significantly enhanced the reactivity, affording the desired compounds in excellent chemical yields with short reaction times.
C-H bond functionalization via hydride transfer: synthesis of dihydrobenzopyrans from ortho-vinylaryl akyl ethers
McQuaid, Kevin M.,Long, Jonathan Z.,Sames, Dalibor
supporting information; experimental part, p. 2972 - 2975 (2009/12/05)
The hydride transfer initiated cyclization ("HT-cyclization") of aryl alkyl ethers, which leads to direct coupling of sp3 C-H bonds and activated alkenes, is reported. Readily available salicylaldehyde derived ethers are converted in one step to dihydrobenzopyrans, an important class of heteroarenes frequently found in biologically active compounds. This process has not been previously reported, in contrast to known HTcyclizations of the corresponding fert-amines ("tert-amino effect" reactions).
