60081-07-4Relevant academic research and scientific papers
Diisobutylaluminum hydride-promoted cyclization of benzyl and phenylsilyl ethers bearing a 2-(trimethylsilyl)ethynyl group: syntheses of indenes and benzosiloles
Kinoshita, Hidenori,Fukumoto, Hiroki,Tohjima, Takayuki,Miura, Katsukiyo
, p. 3571 - 3574 (2016/07/18)
The reaction of o-[2-(trimethylsilyl)ethynyl]benzyl methyl ethers with diisobutylaluminum hydride (DIBAL-H) gave 2-(trimethylsilyl)indenes in good yields. This cyclization proceeds by regio- and stereoselective hydroalumination of the alkyne moiety followed by intramolecular nucleophilic substitution. o-[2-(Trimethylsilyl)ethynyl]phenylsilyl methyl ethers also underwent the DIBAL-H promoted-cyclization to be converted into 2-(trimethylsilyl)benzosiloles in good yields. This approach provides straightforward and efficient way to construct benzosiloles from readily available organosilanes.
Synthesis of N-substituted (Z)-3-arylbenzo[c]thiophen1(3H)-imines by the reaction of 1-[aryl(methoxy)methyl]2-lithiobenzenes with isothiocyanates followed by acid-mediated cyclization
Kobayashi, Kazuhiro,Shigemura, Yuuho,Ezaki, Kosuke
, p. 526 - 536 (2015/08/10)
A simple procedure for the preparation of N-substituted (Z)-3-arylbenzo [c]thiophen-1(3H)-imines has been developed. Thus, bromine/lithium exchange between 1-[aryl(methoxy)methyl]-2-bromobenzenes and butyllithium, followed by reaction of the resulting 1-[
Synthesis of spiro[isobenzofuran 1(3H),4' piperidines] as potential central nervous system agents
Bauer,Duffy,Hoffman,Klioze,Kosley Jr.,McFadden,Martin,Ong
, p. 1315 - 1324 (2007/10/05)
Synthesis of 1' methyl 3 phenylspiro[isobenzofuran 1(3H),4' piperidine] (7a, HP 365) and the demethyl analogue 9a (HP 505) was prompted by recognition of an aminoalkyl(aryl)isobenzofuran moiety common to the antidepressants talopram (Lu 3-010) and trans 10,11 dihydro 5,10 epoxy 5 [3 (methylamino)propyl] 5H dibenzo[a,d]cyclohepten 11 ol (MK-940). Convenient laboratory synthesis of 7a was provided by lithiation of 2 bromobenzhydryl methyl ether, followed by addition of 1 methyl 4 piperidone and acid catalyzed cyclization. N Dealkylation by standard methods afforded 9a. Synthesis of analogues was stimulated by discovery of marked inhibition of tetrabenazine induced ptosis for lead compounds 7a and 9a. Optimal antitetrabenazine activity is associated with the 3 phenylspiro[isobenzofuran 1(3H),4' piperidine] moiety where nitrogen is basic. Modification of this moiety by introduction of large nitrogen substituents or a C-3 substituent > H significantly reduced antitetrabenazine activity. A series of analogue with aromatic substituents was investigated; however, few of these compounds were significantly more active than 7a and 9a. Compound 9a was selected for additional studies.
