N-Cyanation of Secondary Amines Using Trichloroacetonitrile
A one-pot N-cyanation of secondary amines has been developed using trichloroacetonitrile as an inexpensive cyano source. A diverse range of cyclic and acyclic secondary amines can be readily transformed into the corresponding cyanamides in good isolated yields, with the method successfully utilized in the final synthetic step of a biologically active rolipram-derived cyanamide. This approach exhibits distinct selectivity when compared to the use of highly toxic cyanogen bromide.
Ayres, James N.,Ling, Kenneth B.,Morrill, Louis C.
supporting information
p. 5528 - 5531
(2016/11/17)
Conjugated addition of bis(oxazolinyl)zinc to substituted 2-nitrovinyl benzenes: an alternative synthesis of (±)-Rolipram
In this letter we present a new 2,4,4-trimethyl-2-oxazoline anion-zinc derivative that has a remarkable thermal stability when compared with the corresponding cyanocuprate counterpart. The yields from conjugated addition to several 2-nitrovinyl benzenes are moderate to good and the reaction itself is easier to execute and cleaner. As an application, this methodology was applied to an alternative synthesis of (±)-Rolipram, a drug with several interesting biological activities.
Oliveira, Alfredo R.M.,Villar, José A.F.P.,Simonelli, Fabio,Gariani, Rogério A.,Wosch, Celso L.,Zarbin, Paulo H.G.
p. 1507 - 1509
(2008/02/02)
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