Indole as a dienophile in inverse electron demand Diels-Alder reactions: reactions with 1,2,4-triazines and 1,2-diazines

Studies with polyfunctionally substituted heteroaromatics: A facile route for the synthesis of polyfunctionally substituted N-aminopyridines, 1,2,4-triazolo[1,5-a]pyridines and isoquinolines

“…Polyfunctionally substituted heteroaromatics are interesting compounds for potential utility as dye intermediates [1,2], agrochemicals [3][4][5], and as pharmaceuticals [6][7][8][9][10]. In the past few years, we have been involved in a program aimed at developing new efficient synthetic approaches for these heteroaromatic compounds utilizing inexpensive starting materials.…”

Tandem Silver‐Catalyzed Cyclization/Nucleophilic Functionalization of 2‐Alkynylindole‐3‐carbaldehyde Oximes to Afford New 2,4‐Disubstituted γ‐Carbolines

“…γ-Carbolines can be synthesized by various strategies, such as the Graebe-Ullmann procedure, [5] Pictet-Spengler cyclization, [6] Fischer or alkyne Pd-or Pd/Cu-catalyzed annulations, [7] ring-closing metathesis, [8] or tandem Suzuki-Miyaura/S N Ar [9] or intramolecular Diels-Alder reactions. [10] Another interesting synthetic pathway, reported by Sakamoto, employs the formation of monosubstituted N-oxide B (Scheme 1) from the corresponding oxime A under basic conditions. [11] However, none of these approaches can simultaneously generate the tricyclic core and provide the correct positioning of various C2 and C4 substituents in a one-pot procedure.…”

New small molecule inhibitors of hepatitis C virus

“…The cycloaddition precursors 3 were prepared by S N Ar displacements following BOC-deprotection of L-tryptophan derivatives 1 on triazine 2 10. In situ trifluoroacetylation of the nitrogen linker, accomplished by treatment with trifluoroacetic anhydride, lowers the LUMO of the heteroaromatic azadiene and thereby enables the cycloaddition to proceed immediately after acylation under the reaction conditions without isolation of intermediate 4 .…”