DR ANTHONY MELVIN CRASTO,WorldDrugTracker, helping millions, A 90 % paralysed man in action for you, I am suffering from transverse mylitis and bound to a wheel chair, With death on the horizon, nothing will not stop me except God................DR ANTHONY MELVIN CRASTO Ph.D ( ICT, Mumbai) , INDIA 25Yrs Exp. in the feld of Organic Chemistry,Working for GLENMARK GENERICS at Navi Mumbai, INDIA. Serving chemists around the world. Helping them with websites on Chemistry.Million hits on google, world acclamation from industry, academia, drug authorities for websites, blogs and educational contribution

Monday, 20 March 2017

Regioselective access of alkylidendibenzo[c,f]oxocine framework via cyclocarbopalladation/cross-coupling cascade reactions and reductive Heck strategy

Regioselective access of alkylidendibenzo[c,f]oxocine framework via cyclocarbopalladation/cross-coupling cascade reactions and reductive Heck strategy

New J. Chem., 2017, Advance Article
DOI: 10.1039/C6NJ03825E, Paper
a
Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany
E-mail: tapas.ghosh@uni-wuerzburg.de,tapasghosh.chem@gmail.com
Tel: +49-931-31-81629
New J. Chem., 2017, Advance Article
DOI: 10.1039/C6NJ03825E
Palladium-catalyzed dual strategies of cascade cyclocarbopalladation/cross-coupling of alkynes and a reductive Heck reaction have been developed to construct dibenzo[c,f]oxocine frameworks with tri- and tetra-substituted exo-cyclic alkenes with high stereo- and regio-control.
Palladium-catalyzed dual strategies of cascade cyclocarbopalladation/cross-coupling of alkynes and a reductive Heck reaction have been developed to construct dibenzo[c,f]oxocine frameworks with tri- and tetra-substituted exo-cyclic alkenes with high stereo- and regio-control. The success of this efficient methodology has been demonstrated by the synthesis of a number of dibenzoxocines in moderate to good yields and in sufficient quantities to support their further development.
 
 
12-benzylidene-7,12-dihydro-5H-dibenzo[c,f]oxocine (8a): The material obtained after workup was subjected to column chromatography on silica gel with petroleum ether/EtOAc (19:1) as eluent to deliver pure 8a. Off white solid, yield = 82%,
 
mp. 134-136 oC,
 
IR (KBr): 2861, 1623, 1602 cm-1 , 1H NMR (400 MHz, CDCl3): δH = 7.47 (d, 1H, J = 7.2 Hz), 7.19-7.34 (m, 5H), 7.05-7.15 (m, 5H), 6.94-6.96 (m, 2H), 6.64 (s, 1H), 4.87 (s, 2H), 4.75 (s, 2H).
 
13C NMR (100 MHz, CDCl3): δC = 144.6, 142.1, 138.3, 137.4, 136.9, 129.9, 129.1, 128.9, 128.6, 128.3, 128.1, 127.9, 127.4, 127.0, 126.7, 73.0, 70.3.
 
HRMS (ESI [M+Na]+ ): for C22H18O calcd 321.1255; found 321.1245.
 
 
 
///////Regioselective, alkylidendibenzo[c,f]oxocine, cyclocarbopalladation/cross-coupling cascade reactions, reductive Heck strategy