82971-74-2Relevant academic research and scientific papers
Electrochemical synthesis of isobenzofuran-1-imines using oxidative halocyclization ofo-alkynylbenzamides
Anandhan, Ramasamy,Bhagavathiachari, Muthuraaman,Bhargava Reddy, Mandapati,Peri, Rajagopal
supporting information, p. 6792 - 6796 (2021/08/20)
Electrochemical oxidative 5-exo-dig-oxo-halocyclization ofo-alkynylbenzamides was achieved using readily available NaX (X = Cl, Br and I) salts under mild reaction conditions. The use of a cheap and highly stable sodium halide as a halide ion source is im
Synthesis of 11,12-dihydro benzo[c]phenanthridines via a Pd-catalyzed unusual construction of isocoumarin ring/FeCl3-mediated intramolecular arene-allyl cyclization: First identification of a benzo[c]phenanthridine based PDE4 inhibitor
Ghule, Shailendra S.,Hossain, Kazi Amirul,Kumar, Jetta Sandeep,Mathew, Jessy E.,Mounika, Guntipally,Mudgal, Jayesh,Pal, Manojit,Parsa, Kishore V. L.,Reddy, Gangireddy Sujeevan,Shenoy, Gautham G.,Thirupataiah, B.
supporting information, (2020/03/06)
In spite of their various pharmacological properties the anti-inflammatory potential of benzo[c]phenanthridines remained underexplored. Thus, for the first time PDE4 inhibitory potential of 11,12-dihydro benzo[c]phenanthridine/benzo[c]phenanthridine was a
Green preparation method of 3-hydroxy isoindole-1-one compounds
-
, (2020/01/03)
The invention discloses a green preparation method of 3-hydroxy isoindole-1-one compounds, and belongs to the technical field of organic synthesis. The method comprises the following steps: adopting 2-alkynyl benzamide as a reaction substrate, adding a br
Regio- and Stereoselective Synthesis of Isoindolin-1-ones through BuLi-Mediated Iodoaminocyclization of 2-(1-Alkynyl)benzamides
Brahmchari, Dhirendra,Verma, Akhilesh K.,Mehta, Saurabh
supporting information, p. 3339 - 3347 (2018/03/23)
A simple and straightforward synthesis of isoindolin-1-ones is reported. Exclusive N-cyclization of the amide functional group, an ambident nucleophile, was accomplished for the cyclization of 2-(1-alkynyl)benzamides using n-BuLi-I2/ICl. The methodology works with the primary amide and affords the desired isoindolinones in yields of 38-94%. Interestingly, the isolated products exhibit a Z-stereochemistry across the C=C double bond. The reaction mechanism involving the formation of either a vinylic anion or an intimate ion pair intermediate is proposed.
PhI(OCOCF3)2-Mediated Cyclization of o -(1-Alkynyl)benzamides: Metal-Free Synthesis of 3-Hydroxy-2,3-dihydroisoquinoline-1,4-dione
Yang, Chao,Zhang, Xiang,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
, p. 5320 - 5328 (2015/05/27)
The synthesis of an undocumented skeleton of 3-hydroxy-2,3-dihydroisoquinoline-1,4-diones has been discovered and reported. The reaction consists of an intramolecular cyclization of o-(1-alkynyl)benzamides in MeCN/H2O, mediated by metal-free, h
Divergent palladium iodide catalyzed multicomponent carbonylative approaches to functionalized isoindolinone and isobenzofuranimine derivatives
Mancuso, Raffaella,Ziccarelli, Ida,Armentano, Donatella,Marino, Nadia,Giofrè, Salvatore V.,Gabriele, Bartolo
, p. 3506 - 3518 (2014/05/06)
2-Alkynylbenzamides underwent different reaction pathways when allowed to react under PdI2-catalyzed oxidative carbonylation conditions, depending on the nature of the external nucleophile and reaction conditions. Thus, oxidative carbonylation of 2-ethynylbenzamides, bearing a terminal triple bond, carried out in the presence of a secondary amine as external nucleophile, selectively led to the formation of 3-[(dialkylcarbamoyl)methylene]isoindolin-1- ones through the intermediate formation of the corresponding 2-ynamide derivatives followed by intramolecular nucleophilic attack by the nitrogen of the benzamide moiety on the conjugated triple bond. On the other hand, 3-[(alkoxycarbonyl)methylene]isobenzofuran-1(3H)imines were selectively obtained when the oxidative carbonylation of 2-alkynylbenzamides, bearing a terminal or an internal triple bond, was carried out in the presence of an alcohol R′OH (such as methanol or ethanol) as the external nucleophile and HC(OR′)3 as a dehydrating agent, necessary to avoid substrate hydrolysis. In this latter case, the reaction pathway leading to the isobenzofuranimine corresponded to the 5-exo-dig intramolecular nucleophilic attack of the oxygen of the benzamide moiety on the triple bond coordinated to the metal center followed by alkoxycarbonylation. The structures of representative products have been confirmed by X-ray crystallographic analysis.
Copper-mediated tandem oxidative C(sp2)-H/C(sp)-H alkynylation and annulation of arenes with terminal alkynes
Dong, Jiaxing,Wang, Fei,You, Jingsong
supporting information, p. 2884 - 2887 (2014/06/23)
The copper-mediated tandem oxidative C(sp2)-H/C(sp)-H cross-coupling and intramolecular annulation of arenes with terminal alkynes has been developed, which offers a highly efficient approach to the 3-methyleneisoindolin-1-one scaffold. In this oxidative coupling process, Cu(OAc)2 acts as both the promoter and the terminal oxidant. This protocol features a wide substrate scope; high functional group tolerance; exclusive chemo-, regio-, and stereoselectivity; and simple, easily available, and inexpensive reaction system. The transformation has demonstrated for the first time that Cu(OAc)2 can be renewable after undergoing an oxidative reaction.
A practical protocol for three-component, one-pot, stepwise sonogashira-heterocyclization-heck couplings
Madich, Youssef,Denis, J.Gabriel,Ortega, Aitor,Martinez, Claudio,Matrane, Abdellatif,Belachemi, Larbi,De Lera, Angel R.,Alvarez, Rosana,Aurrecoechea, Jose M.
, p. 2009 - 2017 (2013/07/26)
A three-component, one-pot, stepwise Sonogashira-heterocyclization-Heck- coupling process was developed starting from either haloarenecarboxamides, halophenols or haloanilines, terminal alkynes and electron-deficient alkenes. Cyclic imidate-, benzofuran-,
Synthesis of 1-aminoisoquinolines by gold(III)-mediated domino reactions from 2-alkynylbenzamides and ammonium acetate
Long, Yuhua,She, Zhigang,Liu, Xiaochen,Chen, Yu
, p. 2579 - 2588 (2013/04/24)
A facile synthetic route toward pharmaceutically interesting 1-aminoisoquinoline derivatives by gold(III)-mediated domino reactions is described. This synthetic protocol starts from readily available 2-alkynylbenzamides and ammonium acetate and takes plac
Synergistic effect of palladium and copper catalysts: Catalytic cyclizative dimerization of ortho-(1-alkynyl)benzamides leading to axially chiral 1,3-butadienes
Yao, Bo,Jaccoud, Carole,Wang, Qian,Zhu, Jieping
supporting information; experimental part, p. 5864 - 5868 (2012/06/15)
Two is better than one: In the presence of Pd(OAc)2 and Cu(OAc)2, o-(1-alkynyl)benzamides 1 were converted into bis-iminobenzoisofurans with an axially chiral 1,3-diene 2 unit. The coexistence of both Pd and Cu catalysts was found to be essential for both the cyclizative dimerization process and for the observed unusual cyclization mode. Copyright
