1482520-24-0Relevant articles and documents
Easy and regioselective access to dimethyl acetal-protected heterocycles and their efficient allylation reactions mediated by allylaluminum reagent
Bonacorso, Helio G.,Wiethan, Carson W.,Porte, Liliane M.F.,Moraes, Maiara C.,Navarini, Jussara,Belo, Chaiene R.,Luz, Fabio M.,Zanatta, Nilo,Martins, Marcos A.P.
, p. 291 - 305 (2013/10/21)
This paper describes easy access to twelve examples of five- and six-membered heterocycles (monocyclic and fused) containing a dimethyl acetal aldehyde function and/or a trifluoromethyl substituent, in good to excellent yields (72-98%). The dimethyl acetal-protected heterocycles were obtained in one-step via regioselective cyclocondensation reactions of 4,6,6-trimethoxy-1,1, 1-trifluorohex-3-en-2-one with 1,2-, 1,3- and 1,5-dinucleophiles (hydrazines, hydrazides, hydroxylamine, 1-acetylguanidine and 1,8-diaminonaphthalene). Subsequently, to demonstrate a potential synthetic application, some pyrazole rings containing dimethyl acetal moiety were converted to the respective secondary homoallylic alcohols by efficient allylation reactions employing allylaluminum reagent in 84 to 90% yields.