7402-61-1Relevant articles and documents
Distal γ-C(sp3)?H Olefination of Ketone Derivatives and Free Carboxylic Acids
Fan, Zhoulong,Park, Han Seul,Yu, Jin-Quan,Zhu, Ru-Yi
supporting information, p. 12853 - 12859 (2020/06/10)
Reported herein is the distal γ-C(sp3)?H olefination of ketone derivatives and free carboxylic acids. Fine tuning of a previously reported imino-acid directing group and using the ligand combination of a mono-N-protected amino acid (MPAA) and an electron-deficient 2-pyridone were critical for the γ-C(sp3)?H olefination of ketone substrates. In addition, MPAAs enabled the γ-C(sp3)?H olefination of free carboxylic acids to form diverse six-membered lactones. Besides alkyl carboxylic acids, benzylic C(sp3)?H bonds also could be functionalized to form 3,4-dihydroisocoumarin structures in a single step from 2-methyl benzoic acid derivatives. The utility of these protocols was demonstrated in large scale reactions and diversification of the γ-C(sp3)?H olefinated products.
Improved synthesis of γ-lactones from cyclopropyl cyanoesters
Patel, Nandini C.,Schwarz, Jacob B.,Islam, Khondaker,Miller, Whitney,Tran, Tuan P.,Wei, Yunjing
experimental part, p. 2209 - 2215 (2011/07/07)
Cyclopropyl cyanoesters 2 were reliably converted to c-lactones 4 on treatment with aqueous sulfuric acid. The cyanoesters could be easily prepared from ketones or aldehydes in two steps, making this process particularly attractive from an efficiency standpoint. Copyright
Carboxylate bioisosteres of gabapentin
Burgos-Lepley, Carmen E.,Thompson, Lisa R.,Kneen, Clare O.,Osborne, Simon A.,Bryans, Justin S.,Capiris, Thomas,Suman-Chauhan, Nirmala,Dooley, David J.,Donovan, Cindy M.,Field, Mark J.,Vartanian, Mark G.,Kinsora, Jack J.,Lotarski, Susan M.,El-Kattan, Ayman,Walters, Karen,Cherukury, Madhu,Taylor, Charles P.,Wustrow, David J.,Schwarz, Jacob B.
, p. 2333 - 2336 (2007/10/03)
A series of carboxylate bioisosteres of structures related to gabapentin 1 have been prepared. When the carboxylate was replaced by a tetrazole, this group was recognized by the α2-δ protein. Further characterization of α2-δ binding compounds 14a and 14b revealed a similar pattern of functional in vitro and in vivo activity to gabapentin 1.