150130-06-6Relevant articles and documents
Regioselective ortho-alkylation of N,N-diethylbenzamides via lithiation and copper transmetalation
Pini, Dario,Superchi, Stefano,Salvadori, Piero
, p. C4 - C5 (1993)
One-pot ortho-lithiation and copper transmetalation with CuCN*LiCl of N,N-diethylbenzamides afford the corresponding aryl cyanocuprate, which gives coupling with some aliphatic halides in fair to good yields.
Formal synthesis of angiogenesis inhibitor NM-3
Bauta, William E.,Lovett, Dennis P.,Cantrell Jr., William R.,Burke, Brian D.
, p. 5967 - 5973 (2007/10/03)
We report the formal synthesis of angiogenesis inhibitor NM-3 (1) in six steps from either of the 2,4-dimethoxyhalobenzenes 13a,b or 3,5-dimethoxychlorobenzene (13c). The first key reaction is the regiospecific alkylation/rearrangement between the aryne derived from 13a-c with sodium diethylmalonate in THF to produce diester 11, which after hydrolysis and cyclization affords homophthalic anhydride 3. The second is the reaction of anhydride 3 with either ethyl 2-methylmalonate (28a), in the presence of 1,1′-carbonyldiimidazole, or ethyl-2-methylmalonyl chloride (28b) under basic conditions to afford key isocoumarin 27. The conversion of 27 constitutes a formal synthesis of NM-3.