452094-06-3Relevant academic research and scientific papers
Regioselective synthesis and evaluation of 3-alkylidene-1, 3-dihydroisobenzofurans as potential antidepressant agents
Praveen,Iyyappan,Girija,Kumar, K Suresh,Perumal
body text, p. 451 - 462 (2012/08/07)
3-Alkylidene-1,3-dihydroisobenzofurans exhibited moderate antidepressant activity as evaluated by forced swim and tail suspension test methods. Virtual screening was carried out by docking the designed compounds into the serotonin binding sites of arabinase protein to predict the analogue binding mode of the compounds to the SSRIs. [Figure not available: see fulltext.]
Iodine-mediated electrophilic cyclization of 2-alkynyl-1-methylene azide aromatics leading to highly substituted isoquinolines and its application to the synthesis of norchelerythrine
Fischer, Dirk,Tomeba, Hisamitsu,Pahadi, Nirmal K.,Patil, Nitin T.,Huo, Zhibao,Yamamoto, Yoshinori
supporting information; scheme or table, p. 15720 - 15725 (2009/03/12)
The reaction of 2-alkynyl-1-methylene azide aromatics 1 with iodine and/or other iodium donors, such as the Barluenga reagent (Py2IBF 4/HBF4) and NIS, gave highly substituted cyclization products, namely, the 1,3-disubstituted 4-iodoisoquinolines 2, in good to high yields. Not only simple 2-alkynyl benzyl azides 1a-j and their substituted analogues 1k-u and 6 but also heteroaromatic analogues, including pyridine 8, pyrroles 10a-c, furane 10d, and thiophenes 10e-g, gave the corresponding isoquinoline derivatives in excellent to allowable yields. Electron-donating and electron-accepting substituents on the aromatic ring were equally tolerated, and either acidic or basic (or even neutral) reaction conditions, depending on the reactivity of the substrate, could be applied to smoothly convert the azide starting materials into the desired isoquinoline products in moderate to good yields. Limits were found only in connection with the substituent at the alkyne terminus, where electron-neutral or electron-donating substituents are clearly favored. The iodine-mediated electrophilic cyclization of 1 most probably proceeds through the iodonium ion intermediate 4 followed by nucleophilic cyclization of the azide and subsequent elimination of N2. This new methodology was successfully applied to the short synthesis of norchelerythrine.
Synthesis of 1,3,4-trisubstituted isoquinolines by iodine-mediated electrophilic cyclization of 2-alkynyl benzyl azides
Fischer, Dirk,Tomeba, Hisamitsu,Pahadi, Nirmal K.,Patil, Nitin T.,Yamamoto, Yoshinori
, p. 4764 - 4766 (2008/02/10)
(Chemical Equation Presented) The I's have it: A series of 2-alkynyl benzyl azides have been smoothly converted into 1,3,4-trisubstituted isoquinolines in moderate to excellent yields by an iodonium-mediated synthesis (see scheme). Depending on the struct
Substituent effect on anionic cycloaromatization of 2-(2-substituted ethynyl)benzonitriles and related molecules
Lu, Wen-Der,Lin, Chi-Fong,Wang, Chyi-Jia,Wang, Shih-Jen,Wu, Ming-Jung
, p. 7315 - 7319 (2007/10/03)
Methanolysis of 2-(2-substituted ethynyl)benzonitriles based on the nature of substituents gave 5-exo product, isoindolones and 6-endo product, isoquinolones, respectively. When a bulky substituent, such as tert-butyl group, was employed in this cyclization reaction, a 5-exo adduct was obtained. Phenyl and thienyl groups which can stabilize the α-anion affect the cyclization reaction to produce the 5-exo adducts. Pyridinyl and pyrazinyl groups can also stabilize the α-anion, but the formation of a more stable intermediate by coordination of sodium with nitrogen atom leads to the 6-endo products.
