1417159-94-4Relevant articles and documents
Solid-phase synthesis of N-(buta-2,3-dien-1-yl)amides by the Crabbé reaction
Leikoski, Tuomo,Wrigstedt, Pauli,Matikainen, Jorma,Sipil?, Jussi,Yli-Kauhaluoma, Jari
, p. 38 - 42 (2013)
The Crabbé homologation of polymer-supported propargylamine with paraformaldehyde, CuI, and dicyclohexylamine in 1,4-dioxane at 100 C, followed by cleavage with dilute trifluoroacetic acid, furnishes N-(buta-2,3-dien-1-yl) amides as isolable products. The N-acyltriazene linker on Merrifield resin serves simultaneously as a protecting group for the nucleophilic primary amine. The product diversity is achieved by altering the acyl chloride in the acylation of the triazene linker. In addition to being a new route to nitrogen-containing allenes, our solid-phase method enables immobilization of these reactive cumulated dienes for further synthetic operations.