Producción Científica Profesorado

Preparation of symmetrical C2-C2-linked bis- and tris-6-bromoindoles by Sonogashira couplings and 5-endo-dig cyclization induced by nBu4NF.



Alvarez Hernandez, Alejandro

2016

Raúl Balderrama-Martínez-Sotomayor, Mariana Flores-Jarillo, Alejandro Alvarez-Hernandez. Preparation of symmetrical C2-C2-linked bis- and tris-6-bromoindoles by Sonogashira couplings and 5-endo-dig cyclization induced by nBu4NF. ARKIVOC, 2016 ,(iii), 36-47http://quod.lib.umich.edu/a/ark/5550190.p009.319/1


Abstract


Preparation of symmetrical C2-C2 linked bis-6-bromoindoles and one tris-6-bromoindole containing ether spacers is described. Double regioselective Sonogashira coupling at the C-I bond of benzyl (5-bromo-2-iodophenyl)carbamate with dialkynes allowed preparation of the corresponding bis-benzyl(2-alkynyl-5-bromo)carbamates. Tetrabutylammonium fluoride (TBAF) promoted 5-endo-dig cyclization was successful with substrates derived from alkyldialkynes but failed with substrates derived from aryldialkynes as base catalysis was not sufficient to promote nucleophilic attack on these electron rich alkynes.



Producto de Investigación




Artículos relacionados

Cathepsins X and B Can Be Differentiated through Their Respective Mono- and Dipeptidyl Carboxypeptid...

Stereoselective addition of allylmagnesium chloride to the CN bond of [4.3.0] boron heterobicycles

Facile synthesis of 1,3,6-oxadiazepines from 2,2?-(1,2-ethanediyldiimino)bisphenols

Diastereoselective Synthesis of Spiro-?-lactams via Staudinger Reaction

Synthesis of New Chiral Derivatives of N,N?-Dimethylpropyleneurea (DMPU) and Examination of Their In...

Diastereoselective alkylation of chiral glycinate derivatives containing the ?-phenylethyl group.

Preparation of Seven- and Eight-Membered Boron Heterocycles from Different Salen Ligands and Arylbor...

Aroylthioureas: new organic ionophores for heavy-metal ion selective electrodes

Preparation of N-aryl-substituted spiro-?-lactams via Staudinger cycloaddition

Further insight into three center hydrogen bonding. Participation in tautomeric equilibria of hetero...