- SYNTHESIS OF CYANOCARBOXYLIC ACID ALKYL ESTERS
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Provided is a process for obtaining a compound of formula (I): N≡C-CH2-A-C(O)-OR, wherein Hal is halogen selected from F, Cl, Br or I, A denotes a bond or a divalent spacer selected from alkylene and arylene groups, and R is a C1-4 alkyl group, by reacting a compound of formula (II): Hal-CH2-A-C(O)-OR, wherein Hal is a halogen atom selected from F, Cl, Br and I, and wherein A and R are as defined above, with hydrogen cyanide in the presence of a first base, wherein the molar ratio between hydrogen cyanide and said first base is from 1:0.3 to 1:0.95 and the molar ratio between hydrogen cyanide to the compound of formula (II) is at least 1:1.
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Page/Page column 30-31
(2013/08/28)
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- Synthesis of a γ-lactam library via formal cycloaddition of imines and substituted succinic anhydrides
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Formal cycloaddition reactions between imines and cyclic anhydrides serve as starting point for the synthesis of diverse libraries of small molecules. The synthesis of succinic anhydrides substituted with electron-withdrawing groups is facilitated by new mild conditions for alkylation of aryl-substituted acetyl esters with ethyl bromoacetate. These anhydrides are then used in formal cycloaddition reactions with imines to produce γ-lactams. 2-Fluoro-5-nitrophenylsuccinic anhydride reacts efficiently with imines to provide lactams that are further diversified by conversion of the nitro group to either an aniline and an azide for subsequent reactions with acylating agents and alkynes, respectively. The synthesis of cyanosuccinic anhydride is reported for the first time, and the use of this compound in reactions with imines and subsequent functionalization of the resultant lactams is demonstrated.
- Tan, Darlene Q.,Atherton, Amy L.,Smith, Austin J.,Soldi, Cristian,Hurley, Katherine A.,Fettinger, James C.,Shaw, Jared T.
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scheme or table
p. 218 - 223
(2012/05/07)
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