437611-93-3Relevant academic research and scientific papers
A gold(i)-catalyzed intramolecular tandem cyclization reaction of alkylidenecyclopropane-containing alkynes
Fang, Wei,Wei, Yin,Shi, Min
supporting information, p. 11666 - 11669 (2017/11/03)
A novel gold(i)-catalyzed intramolecular tandem cyclization reaction of ortho-(arylethynyl)arenemethylenecyclopropanes provided an efficient approach to prepare functionalized 11H-benzo[a]fluorene derivatives in moderate to good yields. Further transformations as well as applications of the products have been presented and a plausible reaction mechanism has also been proposed on the basis of deuterium labeling and control experiments.
Silver-catalyzed domino hydroarylation/cycloisomerization reactions of ortho-alkynylbenzaldehydes: An entry to functionalized isochromene derivatives
Mariaule, Galle,Newsome, Gregory,Toullec, Patrick Y.,Belmont, Philippe,Michelet, Vronique
supporting information, p. 4570 - 4573 (2015/02/19)
A Ag-catalyzed versatile and efficient access to 1H,1-arylisochromenes is reported. Starting from ortho-alkynylbenzaldehydes bearing various substitution patterns on the benzaldehyde and alkynyl units, the use of silver triflate (10 mol %) allowed a domino hydroarylation/cycloisomerization reaction process, leading to aryl-functionalized 1H-isochromene (>10 compounds, 80-98% yields). Notably, the reaction conditions were also compatible with benzaldehydes bearing an aliphatic-substituted alkynyl moiety with modest to good yields (34-88%, 10 compounds).
Regio- and stereoselective construction of highly functionalized 3-benzazepine skeletons through ring-opening cycloamination reactions catalyzed by Gold
Du, Xiangwei,Yang, Shuang,Yang, Jingyu,Liu, Yuanhong
supporting information; experimental part, p. 4981 - 4985 (2011/06/17)
Ring size under control: Highly functionalized 1-amino- or 1-hydroxy-1H-benzo[d]azepines have been prepared through a gold-catalyzed cyclization of (o-alkynyl)phenyl aziridines with heteronucleophiles. After removal of the phthalimido group, the products can be further transformed into 1H-benzo[d]azepin-1-ones (see scheme; IBX=2-iodoxybenzoic acid, Phth=pthalimido).
Functionalization of Csp3-H bond-Sc(OTf)3-catalyzed domino 1,5-hydride shift/cyclization/Friedel-Crafts acylation reaction of benzylidene Meldrum's acids
Mahoney, Stuart J.,Moon, David T.,Hollinger, Jon,Fillion, Eric
, p. 4706 - 4709 (2011/03/18)
Under Sc(OTf)3 catalysis, benzylidene Meldrum's acids bearing a tethered p-methoxyphenethyl group were observed to undergo a [1,5]-hydride shift/cyclization at room temperature, representing a mild Csp3-H bond functionalization. The resulting spiro Meldrum's acid intermediates then underwent intramolecular Friedel-Crafts acylation, completing the one-pot, domino reaction. The reported protocol generates the 6-6-5-6 tetracyclic core of tetrahydrobenzo[b]fluoren-11-ones.
Synthesis of substituted isoquinolines by electrophilic cyclization of iminoalkynes
Huang, Qinhua,Hunter, Jack A.,Larock, Richard C.
, p. 3437 - 3444 (2007/10/03)
The tert-butylimines of o-(1-alkynyl)benzaldehydes and analogous pyridinecarbaldehydes have been cyclized under very mild reaction conditions in the presence of I2, ICl, PhSeCl, PhSCl, and p-O2-NC6H4SCl to give the corresponding halogen-, selenium-, and sulfur-containing disubstituted isoquinolines and naphthyridines, respectively. This methodology accommodates a variety of iminoalkynes and affords the anticipated heterocycles in moderate to excellent yields. Monosubstituted isoquinolines and naphthyridines have been synthesized by the metal-catalyzed ring closure of these same iminoalkynes. The silver-catalyzed ring closure is highly effective in cyclizing aryl-, alkenyl-, and alkyl-substituted iminoalkynes at 50°C.
