1204773-61-4Relevant articles and documents
Base-mediated stereospecific synthesis of aryloxy and amino substituted ethyl acrylates
Kabir, M. Shahjahan,Namjoshi, Ojas A.,Verma, Ranjit,Lorenz, Michael,Phani Babu Tiruveedhula,Monte, Aaron,Bertz, Steven H.,Schwabacher, Alan W.,Cook, James M.
, p. 300 - 310 (2012)
The stereospecific synthesis of aryloxy and amino substituted E- and Z-ethyl-3-acrylates is of interest because of their potential in the polymer industry and in medicinal chemistry. During work on a copper-catalyzed cross-coupling reaction of ethyl (E)- and (Z)-3-iodoacrylates with phenols and N-heterocycles, we discovered a very simple (nonmetallic) method for the stereospecific synthesis of aryloxy and amino substituted acrylates. To study this long-standing problem on the stereoselectivity of aryloxy and amino substituted acrylates, a series of O- and N-substituted nucleophiles was allowed to react with ethyl (E)- and (Z)-3-iodoacrylates. Screening of different bases indicated that DABCO (1,4-diazabicyclo[2.2.2]octane) afforded successful conversion of ethyl (E)- and (Z)-3-iodoacrylates into aryloxy and amino substituted ethyl acrylates in a stereospecific manner. Herein are the details of this DABCO-mediated stereospecific synthesis of aryloxy and amino substituted E- or Z-acrylates.
First application of an efficient and versatile ligand for copper-catalyzed cross-coupling reactions of vinyl halides with N-heterocycles and phenols
Kabir, M. Shahjahan,Lorenz, Michael,Namjoshi, Ojas A.,Cook, James M.
supporting information; experimental part, p. 464 - 467 (2010/05/18)
[Chemical equaction presented] 2-Pyridin-2-yl-1H-benzoimidazole L3 is presented as a new, efficient, and versatile bidentate N-donor ligand suitable for the copper-catalyzed formation of vinyl C N and C O bonds. This inexpensive and easily prepared ligand facilitates copper-catalyzed cross-coupling reactions of alkenyl bromides and Iodldes with N-heterocycles and phenols to afford the desired cross-coupled products In good to excellent yields with full retention of stereochemistry. This method is particularly noteworthy given Its efficiency, that is, mild reaction conditions, low catalyst loading, simplicity, versatility, and exceptional level of functional group tolerance.
A new class of potential anti-tuberculosis agents: Synthesis and preliminary evaluation of novel acrylic acid ethyl ester derivatives
Kabir, M. Shahjahan,Namjoshi, Ojas A.,Verma, Ranjit,Polanowski, Rebecca,Krueger, Sarah M.,Sherman, David,Rott, Marc A.,Schwan, William R.,Monte, Aaron,Cook, James M.
experimental part, p. 4178 - 4186 (2010/09/12)
Novel acrylic acid ethyl ester derivatives were synthesized and evaluated as potential agents against Mycobacterium species. A versatile and efficient copper-catalyzed coupling process was developed and used to prepare a library of substituted acrylic acid ethyl ester analogs. Minimum inhibitory concentration assays indicated that two of these compounds 3 and 4 have greater in vitro activity against Mycobacterium smegmatis than rifampin, one of the current, first-line anti-mycobacterial chemotherapeutic agents. Moreover, members of this new class of compounds appear to exhibit a specific anti-mycobacterial effect and do not inhibit the growth of the other Gram-positive or Gram-negative species tested.
