67205-73-6Relevant articles and documents
Further studies on the application of vinylogous amides and β-halovinylaldehydes to the regiospecific synthesis of unsymmetrical, polyfunctionalized 2,3,4- and 1,2,3,4- substituted pyrroles
Gupton, John T.,Shimozono, Alex,Crawford, Evan,Ortolani, Joe,Clark, Evan,Mahoney, Matt,Heese, Campbell,Noble, Jeffrey,Mandry, Carlos Perez,Kanters, Rene,Dominey, Raymond N.,Goldman, Emma W.,Sikorski, James A.,Fisher, Daniel C.
, p. 2650 - 2663 (2018/04/23)
Highly functionalized pyrroles with appropriate regiochemical functionality represent an important class of marine natural products and potential drug candidates. We describe herein a detailed study of the reaction of α-aminoacid esters with vinylogous amides and also β-halovinylaldehydes for the regiospecific synthesis of 2,3,4-trisubstituted and 1,2,3,4-tetrasubstituted pyrroles. Since the vinylogous amides and β-halovinylaldehydes are readily available precursors, rapid access to a wide variety of unsymmetrically substituted pyrroles is accomplished via this methodology.
p-Toluenesulfonic acid-promoted selective functionalization of unsymmetrical arylalkynes: a regioselective access to various arylketones and heterocycles
Jacubert, Maud,Provot, Olivier,Peyrat, Jean-Fran?ois,Hamze, Abdallah,Brion, Jean-Daniel,Alami, Mouad
experimental part, p. 3775 - 3787 (2010/07/04)
Regioselective hydration of a wide range of internal alkynes has been afforded in high to good yields by using PTSA in EtOH. The scope of the reaction of alkynes has been delineated. Arylaliphatic alkynes and diarylalkynes were regioselectively hydrated in good to excellent yields and short reaction times when the reaction was achieved under microwave irradiation. Moreover, diarylalkynes, arylenynes as well as diaryldiynes bearing a methoxy- or a thiomethyl substituent on the ortho position underwent a regioselective 5-endo-dig-cyclization to give a variety of 2-aryl- and 2-styrylbenzofuran or benzothiphene derivatives. We believe that, this new environmentally metal-free procedure combined to microwave irradiation would be in importance in the search of green laboratory-scale synthesis.
Application of the catalytic friedel-crafts acylation reaction and regioselectivity correlations
Wilkinson, Mark C.,Saez, Fabienne,Wei, Lee Hon
, p. 1063 - 1066 (2007/10/03)
A correlation was found between electronic properties and regioselectivity in the Friedel-Crafts reaction of substituted phenylacetic and benzoic acids with anisole, utilising substoichiometric (down to 1 mol%) amounts of catalyst. Relative reactivities of selected catalysts for this reaction were also studied. Georg Thieme Verlag Stuttgart.