143722-49-0Relevant academic research and scientific papers
Glycinamide hydrochloride as a transient directing group: Synthesis of 2-benzylbenzaldehydes by C(sp3)?H arylation
Wen, Fei,Li, Zheng
, p. 3462 - 3474 (2020)
Glycinamide hydrochloride as an inexpensive and commercially available transient directing group for the C(sp3)?H arylation of 2-methylbenzaldehydes is described. A series of practical 2-benzylbenzaldehydes bearing various functional groups are efficiently synthesized in satisfactory yield by this strategy. This method can also be extended to gram scale.
Synthesis of Benzoazepine Derivatives via Azide Rearrangement and Evaluation of Their Antianxiety Activities
Lapmanee, Sarawut,Palavong, Nitwaree,Reamtong, Onrapak,Ruchirawat, Somsak,Thongsornkleeb, Charnsak,Tummatorn, Jumreang
supporting information, p. 1449 - 1458 (2021/09/13)
A new synthetic method for the construction of benzoazepine analogues has been developed employing ortho-arylmethylbenzyl azide derivatives as precursors using an azide rearrangement reaction. In this work, 14 benzoazepine compounds were successfully synthesized in moderate to excellent yields. All synthetic benzoazepines were evaluated for their cytotoxicity against normal human kidney cell line (HEK cell). The results showed that compound 18c had the lowest cytotoxicity (IC50 = 65.68 μM) among tested compounds, which was comparable with the antianxiety drug diazepam (IC50 = 87.90 μM). Based on the cytotoxicity results, five benzoazepine analogues (compounds 18c, 18h, 18j, 18n, and 18p) were selected to determine the antianxiety effect on stressed rats using elevated plus maze (EPM) and open field test (OFT) methods. Interestingly, compound 18c showed better anxiolytic activity than diazepam without a sedative effect by showing superior hyperlocomotor activity. Therefore, this discovery could pave the way for drug development to treat patients with anxiety disorder.
Intramolecular Addition Reactions of Functionalized Arylcarbenes to Arenes
Guth, Michael,Kirmse, Wolfgang
, p. 606 - 613 (2007/10/02)
carbenes with Ar = phenyl (16), 1-naphthyl (20), and 2-furyl (24) have been generated photolytically from appropriate diazo or tosylhydrazone precursors.Intramolecular addition to the arene prevailed in pentane solution, insertion into ortho C-H bonds of the arene being a minor process.On direct photolysis in methanol, intermolecular O-H insertion predominated over intramolecular addition to phenyl and 1-naphthyl groups (kS OH).The ratio of addition to O-H insertion was not affected by benzophenone sensitization in the case of Ar = Ph, but increased strongly in the case of Ar = 1-naphthyl.These data, implying kT > kTS for 20, constitute the first evidence for the addition of triplet arylcarbenes to arenes.Ar = 2-furyl was found to promote the intramolecular addition of both singlet 24 (kS ca. kOH) and triplet 24 (kT > kTS).The reactivity of arenes toward electrophiles (kS) and the stabilization of diradical intermediates (kT) is thought to account for the observed trends.
